I (40F) told a guy (34M) I am seeing that I used to date a criminal when I was younger, and he basically started interrogating me about it. I felt kind of hurt by some of the questions he asked me, and I am not sure if I should continue to see him.

Back when I was like, 17-18 or so, I fell for a guy named Ivan, and we started dating. I knew that Ivan got most of his money from crime, but I didn't really ask many questions because I didn't really want to know. This was in south brooklyn in the 1990s, and I knew a lot of girls who had boyfriends who did stuff like this, and the general gist was to never too many questions about any of it. The most I really knew was that he dealt with something related to imports and exports of electronics and gambling and stuff like that. Anyways, we broke up when I was 19-20 when I went off to college. Even though he was a criminal, he was still a very sweet, very smart guy who largely got pushed into that lifestyle by his family, and I hope he got out of that life and actually made something of himself.

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Anyways, fast forward to today, and I am seeing this guy Tim. Tim is a very nerdy, kind of sheltered guy, and I really like him a lot. We were watching the sopranos together and I mentioned that I dated a guy kind of similar to Christopher (in the show), except he was just a normal criminal for his family and wasn't in the mafia, and also, you know, wasnt as bad as chris obviously. Tim thought I was joking but then I said I was serious and I told him about Ivan, and he looked totally taken aback, like really shocked and surprised. I was like "oh come on, I was a TEENAGER" and he kind of snapped at me and said that was no excuse. Then he started getting kind of rude, asking me how I could possibly be okay with 'blood' money (Ivan was not a violent guy, at all), and how I could possibly be okay with someone who robbed people of their livelihood. I was just confused, obviously by todays standards I would not be okay with that, but I just kept on saying, Tim, I was literally an impressionable teenager, what the hell do you want from me? He then said, literally, "I am sorry if this is rude, but I just find that disgusting to be with him, how do you not feel constant guilt for that?" and I was just seriously upset at that. I was leaving for work either way so its not like I stormed out, but I basically did just leave when he said that. He texted me apologizing and said he didn't mean for that to come off so serious and that he was halfway joking but it came out wrong, but I felt like that was a bit of a cop out.

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Honestly, and this is gonna come off badly, I am not sure if I can be with someone so... moralistic. I mean he seriously came off really judgmental there. I feel like I am not even sure if I can tell about any 'bad' things I have done in my past ever now without him freaking out at me. If I tell him I used to sneak out at night to go to parties is he gonna judge me for 'betraying my parents trust' or something?

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i don't want to break it off with him solely based on this. He is a great guy and we get along very well. But what am I supposed to do? How do I talk to him about why this upset me a lot?

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TL;DR - - boyfriend freaked out at me when I told him I dated a criminal in my teen years.

Submitted February 27, 2021 at 09:48AM by chapsticklm44 https://ift.tt/3b0zUZu