u/Away_Load2282

37 [M4F] #Chicago

How's your week going so far?

Are you out there? Do you exist?

Paging all friendly, cute, inexperienced younger girls looking for an older guy.

Are you 18-21? Perhaps near Chicago? I'm looking for you!

About me:

I'm a 37 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 8 hours ago

37 [M4F] #Chicago - I want to be your older brother figure (with benefits)

How's your week going so far?

Are you out there? Do you exist?

Paging all friendly, cute, inexperienced younger girls looking for an older guy.

Are you 18-21? Perhaps near Chicago? I'm looking for you!

About me:

I'm a 37 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 8 hours ago

37 [M4F] #Chicago - I want to be your older brother figure (with benefits)

How's your week going so far?

Are you out there? Do you exist?

Paging all friendly, cute, inexperienced younger girls looking for an older guy.

Are you 18-21? Perhaps near Chicago? I'm looking for you!

About me:

I'm a 37 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 8 hours ago

37 [M4F] #Chicago

How's your week going so far?

Are you out there? Do you exist?

Paging all friendly, cute, inexperienced younger girls looking for an older guy.

Are you 18-21? Perhaps near Chicago? I'm looking for you!

About me:

I'm a 37 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 3 days ago

37 [M4F] #Chicago - Searching for that elusive age gap connection: something real, reliable, healthy and fun. Does it even exist?

How's your week going so far?

Are you out there? Do you exist?

Paging all friendly, cute, inexperienced younger girls looking for an older guy.

Are you 18-21? Perhaps near Chicago? I'm looking for you!

About me:

I'm a 37 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 3 days ago

37 [M4F] #Chicago - Searching for that elusive age gap connection: something real, reliable, healthy and fun. Does it even exist?

How's your week going so far?

Are you out there? Do you exist?

Paging all friendly, cute, inexperienced younger girls looking for an older guy.

Are you 18-21? Perhaps near Chicago? I'm looking for you!

About me:

I'm a 37 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 3 days ago

37 [M4F] #Chicago

Yes, like a real, actual connection. Hopefully in person, too!

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

I'm a 37 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

Society might not love it. But age gaps are normal and they're fun as hell.

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 7 days ago

37 [M4F] #Chicago - Want to get some good experience and guidance before you leave for college?

Yes, like a real, actual connection. Hopefully in person, too!

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

I'm a 37 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

Society might not love it. But age gaps are normal and they're fun as hell.

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 7 days ago

37 [M4F] #Chicago - Want to get some good experience and guidance before you leave for college?

Yes, like a real, actual connection. Hopefully in person, too!

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

I'm a 37 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

Society might not love it. But age gaps are normal and they're fun as hell.

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 7 days ago

37 [M4F] #Chicago - Is it bad that I want a genuine, healthy connection with a girl half my age?

Yes, like a real, actual connection. Hopefully in person, too!

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

I'm a 36 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

Society might not love it. But age gaps are normal and they're fun as hell.

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 10 days ago

37 [M4F] #Chicago

Yes, like a real, actual connection. Hopefully in person, too!

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

I'm a 36 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

Society might not love it. But age gaps are normal and they're fun as hell.

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 10 days ago

37 [M4F] #Chicago - Is it bad that I want a genuine, healthy connection with a girl half my age?

Yes, like a real, actual connection. Hopefully in person, too!

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

I'm a 36 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

Society might not love it. But age gaps are normal and they're fun as hell.

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 10 days ago

36 [M4F] #Chicago - Is it bad that I want a connection with a girl half my age?

Yes, like a real, actual connection. Hopefully in person, too!

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

I'm a 36 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

Society might not love it. But age gaps are normal and they're fun as hell.

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 14 days ago

36 [M4F] #Chicago

Yes, like a real, actual connection. Hopefully in person, too!

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

I'm a 36 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

Society might not love it. But age gaps are normal and they're fun as hell.

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 14 days ago

36 [M4F] #Chicago - Is it bad that I want a connection with a girl half my age?

Yes, like a real, actual connection. Hopefully in person, too!

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

I'm a 36 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

Society might not love it. But age gaps are normal and they're fun as hell.

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 14 days ago

Yes, like a real, actual connection. Hopefully in person, too!

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

I'm a 36 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

Society might not love it. But age gaps are normal and they're fun as hell.

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 17 days ago

Yes, like a real, actual connection. Hopefully in person, too!

If you're lurking around these parts of reddit and curious about older guys, I'd love to hear from you!

I'm a 36 year old, single, white guy. I'm successful, normal, social, have a demanding job, my own condo in a great city (Chicago) and lots or hobbies. I've never been married. Never had kids.

I have a car, I skateboard places, play on lots of rec sports teams, and I'm even a musician (sometimes). I have lots of house plants, am decent at cooking, and love traveling.

I'm basically the definition of a stable, normal, liberal progressive older bachelor.

What am I looking for? No need to hide it or be shy about it. I want a hot, fun, positive, respectul, taboo age gap.

Whether this is just chat, a one-time meetup, a multuple time meetup, or a serious relationship? Well, I think all of those options should be on the table, depending on the chemistry and vibes.

I love the idea of being a stable respectful older influence in your life. Like an older brother figure, teacher, mentor. Someone like that. (But the kind of older mentor figure that gets to have an intimate relationship or interactions with you, if you know what I mean.)

Society might not love it. But age gaps are normal and they're fun as hell.

I would actually consider a real, stable, healthy age gap relationship with someone way younger than me. And I don't think that's crazy at all.

If you're out there, and you're reading this, don't by shy. Reach out and hit me up. I want to talk to you. Even if you're on the fence.

And if you're close (Chicago area or maybe a little further), which I hope you are, maybe we can meet up.

Some things I especially like: athletic girls, nerdy girls, shy girls, inexperienced girls, nice girls who NOBODY would ever believe was talking to an older guy. There's also something insanely hot about younger girls who are on birth control 🀀 (not required, but hey, a guy can dream, right?).

It's totally okay if you're inexperienced, never done anything like this before, afraid, curious, etc. If you're lurking on reddit and on fence about replying, please hmu. I want to hear from you! I don't bite. I'm friendly.

A lot of girls seem to think being a virgin is a turn off or disqualifies you. It totally isn't. In fact, it might make me MORE interested.

Hopefully you are actually interested in chatting at the very least. If the chemistry and trust is there, I'd be game for meeting up or maybe voice chatting and seeing where it goes.

We can flirt, talk about you, talk about me, talk about experience (or lacktherof), clothing, cute outfits, romance, sex, hobbies, or even plan our first meetup. Maybe we can play dressup? You can wear cute clothes for me. Or we can meet up in public and mess around somewhere?

As long as you're 18+. Let's do this.

Tell me about you! Age, location, interests. Would you actually meet up with an older guy? What are you studying? I'd love to get to know you.

If you can't tell me age and location, I'll assume you're a bot.

reddit.com
u/Away_Load2282 β€” 17 days ago

Hey there.

So there was a big prom part on my street last Saturday and wow... some of these dresses were 😳🫨🀀

Do girls that age know that we're checking them out? I mean c'mom!

Any 18F HS seniors out there going to prom this week or next week and like the idea of an older man checking them out in their prom dress?

Is that bad?

Tell me about your dress! Are you going with a date? Any fun plans after?

I'm 36m, white, single, and normal (well, except for being a bit of a perv I guess). But I'm friendly and would love to chat with you about your prom dress. Or who knows. Maybe you live nearby and want to show your dress off πŸ‘€

Plenty of fun scenarios to think about. Being your prom date. Or picking you up after prom to take your v-card. Is it getting hot in here or is it just me?

reddit.com
u/Away_Load2282 β€” 21 days ago

Hey there.

So there was a big prom part on my street last Saturday and wow... some of these dresses were 😳🫨🀀

Do girls that age know that we're checking them out? I mean c'mom!

Any 18F HS seniors out there going to prom this week or next week and like the idea of an older man checking them out in their prom dress?

Is that bad?

Tell me about your dress! Are you going with a date? Any fun plans after?

I'm 36m, white, single, and normal (well, except for being a bit of a perv I guess). But I'm friendly and would love to chat with you about your prom dress. Or who knows. Maybe you live nearby and want to show your dress off πŸ‘€

Plenty of fun scenarios to think about. Being your prom date. Or picking you up after prom to take your v-card. Is it getting hot in here or is it just me?

reddit.com
u/Away_Load2282 β€” 21 days ago

Hey there.

So there was a big prom part on my street last Saturday and wow... some of these dresses were 😳🫨🀀

Do girls that age know that we're checking them out? I mean c'mom!

Any 18F HS seniors out there going to prom this week or next week and like the idea of an older man checking them out in their prom dress?

Is that bad?

Tell me about your dress! Are you going with a date? Any fun plans after?

I'm 36m, white, single, and normal (well, except for being a bit of a perv I guess). But I'm friendly and would love to chat with you about your prom dress. Or who knows. Maybe you live nearby and want to show your dress off πŸ‘€

Plenty of fun scenarios to think about. Being your prom date. Or picking you up after prom to take your v-card. Is it getting hot in here or is it just me?

reddit.com
u/Away_Load2282 β€” 24 days ago