Search Results: bringing up the past

Disclaimer: I am not trying to pursue anything since he’s married.. I do find him very attractive. He’s an executive of my company who’s the boss of my boss.

Earlier this year some very unfortunate family death happened. I was a mess, tried to quit the job with no notice. Surprisingly he reached out to me and convinced me to stay. We had a conversation that I opened up to him and was totally vulnerable. He was very understanding and offered me a month off ( mind you I was only 2 months into the job). When I came back, I noticed he became more attentive. He would come to my desk and tried to initiate a conversation. We don’t really have a lot in common so he would always ask about my pets, nagged me to bring pictures of them and even offered to print out their pictures for me 😂. He would assign project for me to work with him directly. He skipped an interview with a candidate to attend a welcome back group lunch with me.

I was so depressed in the past few months and lost 30pounds in a few months and so physically I looked very different now. I felt like he looked at me differently and sometimes he checks me out. When I recently dyed my hair, none of the other male coworkers said anything except him. He asked if I changed my hair color and told me it looks good.. Last week he came by my desk and asked me what my Halloween costume was for the work party. It’s a pretty obvious one. I asked him you can’t tell? He paused, looked at me up and down and claimed he doesn’t know lol. Then when I told him what my costume is, he had an smile as if he already knew it and just waited for me to say it out..

He approached me less recently ever since I started acting colder to him. Now he spent more time talking to my boss, who’s married and physically I wouldn’t say she’s his type? He still try to chat with me briefly when he came to talk to her. But then there’s times he initiated a conversation and excused himself abruptly? Not sure if it’s all just in my head.

Fresh friendship, a few months in, we bonded over being counselors to youth at a camp. I had no intentions of even remotely considering someone so young for me, but somehow I find myself seriously attracted to him and despite the age difference, we surprisingly have so much in common. He's even discussed how, despite his age, he's ready to find the one, marry and have kids, that he's tired of games with those his age. (not that I've even remotely brought that subject up to him, as we are not currently involved romantically).

I think there are times when it's apparent and undeniable when you have that chemistry with someone and you both can feel it and you know, but it's left unsaid. He recently just found out that my ex was 5 years younger than me and he honestly seemed shocked by it and looked over at my close friend and said, "well she sure likes the young one's doesn't she?" to which she teasingly replied while looking at him, "she sure does." He is 20, about to be 21 and I am 29 soon to be 30, like I said, a significant age difference. I know this is totally unorthodox. We made friends with one another before we knew the age difference.

The chemistry, the bonding, the flirting, it's all there, except he is not taking steps to advance, and neither am I, since I am the woman and I'm older, I do not want to come across as weird or overstep. Is it possible that while there may be attraction and all the right connections there, that he just will not consider it because of our age difference? Guys, what's your opinion? If you bonded so amazing with someone older than you, even if you had feelings, would you refuse to take it any further because of the age difference?