Girl, I don’t even know you- I couldn’t give a shit what you think.
ETA- replying to Rubystreak, obviously… all done shitting in your thread now, ready! 
Look at that, ready#####! You’ve got three gals in here arguing over you and what you should do. Good on you, buddy!
FWIW, I would never mention it to her. Ever. Just get over it, or move on; those are really your only two options. I’ve been in a similar situation. My course of action is probably unorthodoxed, but I bet when you start having sex with her, thoughts of them having sex together will become less frequent and less intense. Unless you land yourself a virgin, you’re probably going to meet somebody’s ex. You’re probably not going to like most of them. Might as well get used to it now.
Thanks for sharing that. You’ve definitely shown my characterization of “harsh” to be way off base. 
Don’t care much what you think either, and really, wasn’t even addressing much of what you said, except as it contributed to a general tone of the thread. Trying to offer the OP a different point of view than the monolithic one thus far presented. Why you’d choose to take it personally, I don’t know, but I’m over it if you are.
Anyway, back to the OP. Good luck with it. Part of you knows what to do. Just figure out which part it is and listen to it. Simple, right?
What the hell does he have to do with you and your life with her? Stop being a drama llama and get on with your life. Obsessing over an ex is borderline weird and unsavory.
“You’re out with your new love slave and you run into your former love slave. And the new one goes ‘You were obsessed over him?’ ‘Yes, but post-breakup disclaimer, okay? Imagine him with a human head.’” - Judy Tenuta
Why not ask her (diplomatically) what she saw in him? He may have some unseen redeemable qualities that will make him less repugnant to you. Then again, maybe he just had good drugs…
Well, if she dated him, he probably had some good points. Maybe he was hung like a can of Pingles?
Get over it.
or Pringles
Razorette and I met each other (as I think I have mentioned previously) while on the rebound from other relationships. Difference was, she was bouncing a lot harder than I was. The guy was a complete head case with a faked auto accident in his past, drugs in his pockets and jail in his future. He and I actually had a brief, very minor confrontation and, except for hearing occasionally that he’d been arrested, then imprisoned, then paroled, then moved to another state, I gave him no more thought. More than 10 years after my wife and I married, as we were going through a particularly difficult time, relationship-wise, she decided to tell me the whole ugly story about her affair with the guy. It was cathartic for her, epiphaneal for me, and when it was all over she thanked me or not asking me about him for all those years. She just wasn’t ready to talk about it.
Look, we all do things that seem like a great idea at the time but later don’t look all that bright. If it was a major thing in her life, and if you last that long with her, someday she’ll tell you. Until then, enjoy her for who she is.
Would it be better if he was a smooth, hot as fuck bazillionaire who’s notoriously good in bed? Would you be left wondering ‘Shit what does she see in me?’
Anyway, I hope this is just about this one guy. Yes, for most people seeing an ex in the flesh is sort of weird and occasionally infuriating– partly out of fear that your partner will go back to them, or that you’ll be next– but sometimes there’s a creepy, hypocritical ‘I don’t want damaged goods’ angle, which, again, hopefully isn’t the case here.
I’m wth 29003 on this one as far as the emotional side of it goes. There are no skeletons in my dating closet and I expect the same of the people I date. The last reunion I went to I had multiple former girlfriends talking to me at the same time. You could look from one to the other and see a quality person. That doesn’t mean all former mates have to be perfect but I expect them not to be sleezeballs.
With that said, I’ve seen some of the sweetest, smartest most beautiful women from the best of families’ date the most screwed up men imaginable. It’s not a myth that women like to date bad boys. I’ve seen it over and over again. Age is certainly a part of this and should be taken into account but I’m not interested in dating a doormat. That is what my conversation would be about with the lady in question. If this can’t be discussed and dealt with as a couple then the relationship is doomed.
Thank you. And I’m sorry, I was inordinately snarky.
ready, I’m a very toughlove, pragmatic, “there’s no crying in baseball!” kind of person. I realize that sometimes comes off a little harsh (it sounds neutral in my head, I swear!), so my apologies if you felt attacked.
Everyone needs to decide what they can or can’t live with and act accordingly. There’s nothing wrong with deciding this is something you can’t live with (although IMO, it’s a bit shortsighted. You’re not likely to meet many people who will only have slept with guys you approve of.)
What *would *be wrong is to stew over this, let her think everything is okay, and then blindside her with something that you never mentioned, and she can’t do anything about. That **is **immature, and passive-aggressive, and a whole bunch of other things that you don’t want to be.
Been there and it doesn’t make you a bad person to think about this stuff. My wife was married before, to one the biggest sack of shit losers on earth (top ten maybe). Here is some of the thought processes I went through.
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“How could she have gone out with that guy?” You have to remember that the jerks of the world are looking for love too and they are particularly interested in giving and forgiving women, so they end up with the nice girls a lot. Some jerks can be very charming for a short time. Ever had a friend that later turned out to be a jerk?
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“Eww, he has touched her where I am touching her.” Those skin cells are long gone, just like he is. He is not going to be there with the two of you and I’m willing to bet that she won’t be thinking about him when you two are together.
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“Could she see the same thing in me that she saw in him?” That’s a good question, I think. Try to make yourself a better person and try to treat her in a better way, what more can you do?
I could go on and on. After twenty years together I still shake my head and wonder why whenever the thought crosses my mind, like now. But I know she has never looked back. It was a mistake, we all make 'em.
So, to answer your main question: You can ask her “what did you see in that guy” and maybe she will tell you a story about how that all started and maybe you will get some insight. But you can’t ask her to somehow make it go away or expect her to apologize to you for a mistake she made when you didn’t exist in her life. Then you have to either let it go or don’t get into a relationship with her. If you start a relationship with this girl and then start hammering her with guilt over her last boyfriend, well, then you will know how someone can end up dating a jerk.
You may as well learn something. Ask her what she sees in you that reminds her of him.
I’ve decided that, unless he has children with her or got an incurable STD from her, his past relationships and conquests are none of my business. I’ve made some pretty questionable choices in men in my past and I would not appreciate being judged by them today.
I agree, a discussion with her about it is going to lead to nothing good. Either you can take her as she is today, just as she is, or you judge her and I don’t think we have good relationships with people we judge.
Good luck, whatever your decision is.
As someone who has been asked the above question and felt humilated by the experience, all I have to add is an emphatic “this”. (And what HolyFreakingMoly said, too.)
Oh that’ll make him feel better.
OUCH! A can of pringles would hurt…
Just for the record, I don’t know of a single woman who’s ever stayed in a relationship because of someone’s penis size. Sometimes I wish my man’s dick was a little thicker but I certainly wouldn’t leave him for the promise of a fatter dick! At least I don’t think I would.
I’m a fat dick. How you doin’?
The first thing I thought when I read the OP was this: What if the answer sucks?
She might very well say something like: I dunno, the alcoholic controlling losers are all I want to be with. That’s why I love you!
Dude, if you’re happy being with her then leave the skeletons alone and get on about your business.
[Inner Perv]
You sure about that baby, cause I’ve got what you’re looking for. . . heh heh heh.
[/Inner Perv] 