A few years ago I fell for my very best friend. We began dating, and not a week later, a serious crisis occurred in my family and I told him I could not start a relationship under such circumstances. We went our separate ways, and he was very bitter towards me for a while. He immediately began dating a girl, wound up getting her pregnant, and now they are married. Although our friendship suffered serious blows, he will always be someone very dear to me. On occasion we've run into each other at parties, and it's like nothing changed, until a few months ago.
One night we both had a number of cocktails in us and began discussing the unfortunate turn our relationship took. The conversation ended when he grabbed my face and kissed me. Since then, he has contacted me a few times online, asking to hang out. Generally I've ignored these messages, but now he is texting and calling more frequently, asking to just spend a little time with me and talk. I'm not sure how to handle this situation. Spending time alone with a married man with whom I have a past seems inappropriate. I've already caused him to cross the line once, and I refuse to be a part of such a thing again.
All I can think about are his wife and her child, and how this would make me feel if I were in her shoes. Am I overthinking his request? If not, is there a way to handle this without causing any more damage to the memory of our friendship or his marriage?
— Fraught Friendship Fima
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Dear Fraught Friendship Fima,
Wow, this is certainly a complicated situation to find yourself in, although the combination of friendship and more-than-friendly feelings is rarely anything less than complicated. In this case, I think your instincts are absolutely right. The kiss alone was inappropriate enough, but engaging in any other alone time at this point is putting yourself at risk; you don't want to end up in the middle of something you never intended to be a part of. And while it's certainly possible he just wants to get together and talk, it's obvious his feelings for you run far deeper than friendship. He's looking for some kind of satisfaction or closure that he's just not going to get while he's still married.
As hard as it may be, you need to stay away from him. If he persists, clearly state your unwillingness to participate in any questionable behavior. No matter how much he begs or pleads, avoid his attempts to make contact. As far as maintaining a friendship, at this point it doesn't seem possible, does it? The more distance you create, the more likely he is to move on. If he decides to leave his wife and start anew, let that be his choice alone.