Tl;dr should I ask my friend, whom I’ve known for 14 years, and have hooked up with out? I (29F) think I should ask my friend (29M) of 14 years out? We’ve known each other since we were 15, and have managed to keep in touch with each other for the past 14 years. 3 years ago, I was going through a bad breakup and got drunk with this friend. Things started getting handsy and we ended up hooking up that night. It was supposed to be a one time thing and we both decided that we’re not going to date each other, plus he was interested in someone else then. That decision didn’t hold for long, as over the next one year, we hooked up a few more times, as we were both single. During this period, he told me he wasn’t seeing anyone else, but that could’ve been a lie, I’m not sure. After our last hook up in 2024, I told him this has to end because neither of us can actively look for life partners if we keep doing this. We both agreed to keep things strictly platonic from then on. We don’t live in the same city, so after this last hook up I told him I’ll be blocking him, otherwise we might get back to the same pattern again. To this he told me not to block him, as he would still like to know my whereabouts and that I’m doing well in life. For the past 2 years we upheld this and we maintained a strictly platonic friendship. But for the past 6-8 months he started making reaching out to me for the littlest things, things he can just look up online, started letting me know whenever he was in my city, and would make flirty jokes. I once posted about gifts on my story and he asked me when my birthday was (I know he knows my birthday, we were only born a week apart), and then told me that he has set a reminder for my birthday on his phone so he doesn’t miss it. Since then he has indicated multiple times that I should come to his city, and we could hang out. February 2026, he was in my city and asked me if we could meet up. I didn’t want to, for fear we might fall into the same pattern again and end up sleeping together. So I politely made an excuse and didn’t meet him. This month, he was coming to my city again, and told me way in advance about it (like a month in advance). I didn’t offer to meet him but just made a general inquiry about what business he had here etc. Then few days before he was supposed to land, he asked me directly if I would like to meet him. This time I gave in and said okay, we could dinner. The fateful day arrived, we had dinner, caught up on each others lives, and watched a movie together. The whole evening he was making flirty jokes, like “should we get married”?" (since we’re both having trouble finding someone for the long term), and kept “accidentally” touching my arm, thighs. One thing led to another, and we started making out. In my head, I knew I had to stop this before it got out of hand, and kept trying to push him away. I gave him a shove and told him sternly, that we cannot continue with this. We had a talk again after this, and I asked him why we always ended up in the same pattern even though more than 2 years have passed since we last hooked up. We both agreed that this makes the friendship very awkward. It’s not like we have both been deprived of action, we have been with other people in the past 2 years. He had once told me when he used to hook up periodically that he m@t&rb@ted thinking of me, I asked him if he still did, and he answered “yes.” I asked him why, he said he doesn’t know why, that he just thinks of the last time we hooked up and does it. Is it normal for guys to do this? submitted by /u/Ok-Sector-444
Originally posted by u/Ok-Sector-444 on r/AskMen
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