34M working with my 58F MIL — am I completely overthinking this?
34M working with my 58F MIL — am I completely overthinking this?
I’m 34M and have been with my wife for 10 years. I also work with my 58F mother-in-law. Before anything else, I want to make a few things clear: my MIL is a very friendly person in general, she is not normally flirty, and she and my daughter are extremely close. I genuinely don’t believe she would intentionally cross a serious line with me.
One other important piece of context: she is extremely unhappy/miserable in her marriage. She has talked about being unhappy with her husband, and I know their sex life is basically nonexistent. I don’t know if that has anything to do with any of this, but I figured it was relevant.
That being said, there have been a few things over the years that have made me wonder if she may be trying to get my attention, and I’m curious whether I’m completely overthinking it.
We work in a relatively small office with only six people. My desk is somewhat isolated and happens to be right next to the printer, which she uses every day.
Almost every day, when she goes to the printer, she’ll bend over with her butt facing toward me. Sometimes she’ll grab her belt loops and pull her pants up in a way that exposes her butt a little. She does things along those lines pretty frequently, and not necessarily just at the printer. She’ll also be walking by me and stop right after she passes me (to where her butt is right in front of me) to read a message on her Apple Watch for a few seconds, then walks away.
It could absolutely be that she’s completely oblivious to how it looks. She’s a very casual, comfortable person and may simply not think anything of it.
But because it happens so frequently and often directly in front of me, a part of me wonders if it’s intentional.
She also texts me pretty casually and uses emojis, extra exclamation points, etc. But again, I think that may simply be how she communicates with everyone, so I don’t know if that means anything.
**Now for the important context: I have actually crossed the line myself a few times.**
A couple of years ago, I intentionally sent her a picture of my erection through my boxers with the message, “hurry home,” trying to make it look like I had accidentally sent it to her when I meant to send it to my wife.
She opened it but didn’t respond.
The next morning, I messaged her on Snapchat pretending to be horrified that I had accidentally sent it to her. She said it was okay, that it would stay between us, and that nothing would be awkward moving forward. She said she basically closed the Snap immediately when she realized what it was.
I then stupidly pushed it further and told her she didn’t have to lie because I knew she had looked at it for a while. She laughed and denied it.
We went back and forth for a little while with me making some pretty obvious comments. She never really encouraged me, but she also didn’t react angrily or shut the conversation down immediately.
Eventually, she told me I needed to behave myself because I was married to her daughter. I apologized and agreed.
The second incident happened when I sent her a Snap of two margaritas and said I’d save one for her. During the conversation, I essentially called her a MILF.
She responded with laughing emojis and said thank you. I left it alone.
The most recent incident happened while I was working from home. I sent her a Snap about work, we had some normal small talk, and then I randomly asked if I could ask her something personal.
She said sure.
I asked how often she and her husband had sex. She said a few times a year.
I told her that was a shame because a woman like her should be doing it much more often.
Again, she wasn’t really reciprocating, but I got the impression that part of her was enjoying the conversation. I then took it way too far and told her that if she were mine, I’d make sure she was getting it a lot more often.
She responded that what I was saying made her uncomfortable.
I immediately felt like an idiot, apologized, and told her I was sorry.
She said it was okay, that we were all good, and that we’d just move on like nothing happened.
And that’s what we’ve done.
Since then, nothing has really changed. She still does the bending over in front of me, pulling her pants up with her butt facing me, etc.
So here’s where I’m stuck.
I realize I am probably not the most objective person here because I’ve obviously sexualized the situation myself. I also realize that I’ve given her plenty of opportunities to tell me to fuck off, and she hasn’t completely cut me off or made things awkward.
But at the same time, she has never actually reciprocated my advances, and the one time I clearly went too far, she explicitly told me I made her uncomfortable.
Her being miserable in her marriage also makes me wonder whether I’m interpreting things differently because I know she’s unhappy and have that information in the back of my mind.
So am I just being optimistic/delusional and interpreting completely normal behavior as flirting because I’ve already put that idea in my head?
Or is there a possibility she’s aware of what she’s doing and is intentionally walking a very fine line without actually crossing it?
I’m not looking for people to tell me what I want to hear. I’m genuinely curious how this looks from an outside perspective.