A
female
age
36-40,
anonymous
writes:My bf is 31, I am 26 and we have been together for about seven months. Things are going great...however...I'm confused about the fact that all his exes and friends are strippers, ex cons, prostitutes, porn stars ...and generally people who are a little shady. Don't get me wrong, I'm not judgemental, but I don't get why he is with me??! My bf was also in prison for a while (he is a builder now) and he too grew up with an alcoholic mum, and an absent father. I am an educated, middle class, professional. Went to a great uni, no criminal record, pay my taxes etc...I'm what you would call a very boring, dull citizen. I even work as a special constable (police for no pay!) a few times a month. Also, I am a virgin, waiting for the right time (which he respects and doesn't pressure me) What the hell is going on?! Why did he pick me? All his exes are tattooed, sexy belly dancers/strippers, and I'm a boring virgin. I would understand if a guy like me wanted me (as I'm quite attratcive) but not him I am thinking of breaking up with him as I feel really insecure.
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alcoholic, ex girlfriend, his ex, in jail, insecure, porn, prostitute, stripper, tattoo Reply to this Question
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female
reader, maverick494  +, writes (19 July 2012):
Hmm, a very violent offense he kept from you....I'd be careful if I were you. I can understand why he wouldn't want to advertise his past, but it is a red flag even if he ended up telling you about it.
It means he's had trouble keeping himself under control and may still experience this problem. Talk to him extensively about his past and listen to your gut. If you have the feeling he's not telling you the truth or the whole story, bolt. If he displays aggressive behavior, bolt.
In fact, at this point I'd really reconsider the idea of a relationship because you are such different people (and not in a good way). If you want to give him a chance, make sure you set your boundaries and monitor his behavior.
Smart, nice, well spoken people usually don't end up in prison for a "very violent offense".
A
female
reader, anonymous, writes (17 July 2012): OP here:
Thank you all for your replies, you guys raise interesting points, and I will bring this topic up with him- its the only way I will get answers.
As for the question why I picked him...well, I didn't know until a month in that he had been in prison. He was there for about four years, he got seven years, but let out with good time and probation. It was for a very violent offence. I picked him because he seemed really nice when we met, and as I said, I didn't know about the crime. He is smart, well spoke, and very nice.
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A
female
reader, Honeypie + ♥, writes (17 July 2012):
 Well I hope he gets testing for the whole STD battery before you decide you bed him.
You ask why he picked you, but I want to know why YOU picked him.
Maybe he wants to state over with a "clean slate" the other girls weren't exactly "keepers" but maybe they were good to be around or have around.
Maybe this is even a question you should ask him.
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A
female
reader, Denise32 +, writes (16 July 2012):
 You might be familiar with the old adage that people are known by the company they keep?
In other words, him having all these 'shady" friends reflects badly on him - and indirectly, on YOU because he is your boyfriend.
MAYBE he is now a "reformed character." As the other aunts have said, you need to have a serious talk with him. Though don't be accusatory or judgmental. Ask questions and see what he has to say. If he tells you he's given all that up, you'll have to determine whether his statement rings true. If you still have doubts then that is something you must pay attention to.
Good luck!
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A
female
reader, chigirl  +, writes (16 July 2012):
 To answer the headline question.. The answer is to revert the question: Why did you pick him? Someone who sees herself as being full of dignity, being a virgin (not that that alone makes you decent at this time and age), why would you be with someone "dangerous"?
Maybe he was curious to try something new. And, maybe you're curious about him as well. No shame in that.
Try to imagine yourself as more than "boring". You can't possibly be boring. No one wants to be in a relationship with someone they find boring. But just because you haven't set yourself on fire doesn't mean there's no passion in you. You don't have to be a freak to be cool.
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A
female
reader, janniepeg  +, writes (16 July 2012):
 He picks you because the shady women won't do for him anymore. He wants you to fulfill the nurturing role that he never had because his mother was alcoholic. Waiting for the right person is good, it does not mean you can't have exciting sex with him. When you make love it's a much greater feeling than just having sex. You may give him the ultimate loving experience he so needs. He has to come to terms with what he has done in his life, and make sure he doesn't make the same mistakes again. He however can't expect a "perfect" woman like you to come into his life to erase his problems that's if there are still problems affecting this new relationship. Things like trust, compatability, and chemistry are important things too. You are right to feel reservations about this. Just know that his priority right now is not exciting sex, boob size and funky positions. If he is with you that means he wants a change, he wants something stable. It's up to you to find out if he has something equal to offer you.
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A
female
reader, anonymous, writes (16 July 2012): This is something you need to ask him.
My thought is that maybe he is trying to turn his life around. The exes and prison stint seem to indicate he has had a drink/drug problem.
Please communicate with him. Before things become more serious, you need to know why he is with you.
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A
female
reader, maverick494 +, writes (16 July 2012):
There´s a time for play and a time to grow up. Could be that your boyfriend has had enough of that life, the life of taking risks, putting action before thoughts, the thrill and excitement of doing something on the wrong side of the law...and the disappointment when you´re caught. It´s got to get old at one point.
My dad was a drug dealer. When he was 30 and got together with my mom who was a nice educated girl like you, he decided he was going to earn his living the honest way. He still does. I didn´t know about his past until he told me when I was 18.
People can change. You just have to figure out if your bf is one of those. I cannot do that for you. So why not talk to him about it, ask him what his future plans are, and take it from there. Don´t accuse him, just let him explain and listen to your gut.
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