Dating a former student? F30 H20
(Throwaway bc I have a coworker who knows my real account)
To give some context, I met him when he was 14. I was 24; it was my first year of teaching. His mother is a teacher, so he was familiar with the profession and quickly realized it was my first year. He was very kind, joked around with me, and made sure to liven up the classes by participating as much as possible. I could totally see myself in him at that age. We already had a close bond, in a platonic way (though I later wondered if he might have had a crush on me back then—he did everything he could to make me laugh and get my attention). We ran into each other two or three times in the years that followed, but that's all.
We saw each other again in May—he’s now 20 and I’m 30—and I hadn’t seen him since he was in high school. This time, we’ve been seeing each other more often, almost every week for a few hours. He’s become a close friend, and our bond has grown even stronger, since we can now talk about anything. He still has values that I really admire, and he's so kind with me; we have a lot in common and we tease each other a lot. I have to admit that I’m really attracted to him, which surprises me a lot—I’ve always preferred older men; my exes were between 7 and 30 years older than me...
Now I’m wondering if it’s okay to make a move. I’m not sure if he’s attracted to me or if it’s just a friendship, and I don’t want to make him feel uncomfortable. He broke up with his gf of one year in July, he told me he found their conversations and connection superficial and expected more from a relationship, which gives me hope since we spend just as much time teasing each other as we do having deep conversations. But I don't want him to see me as a creep attracted to her students if he's not interested.