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Online Dating Magazine > Columns > Dating Triumphs & Tragedies > Boyfriends in Your Past

Dating Triumphs and Tragedies
by Nicole Roberge

The Drama of Boyfriends Past

My cousin had been on a date with a guy, who she was set up with by a mutual friend, and then later found out that this guy was “intimidated” by her.  First, let me tell you that there’s no need to be intimidate by her—she’s great.  Second, the reason that she intimidated him was because he thought that her ex-boyfriend was a better catch than he was.  Talk about low self-esteem.  And why should he be comparing himself to her ex-boyfriend?  My cousin was starting fresh and looking to date someone new, and clearly was interested in this guy.  That’s what he should have been focused on.

But it is a common thing, I have realized, for guys to compare themselves to past boyfriends, or even former dates of a girl.  They need to know how they measure up and if they are better (or sometimes worse) than the men who have existed in the female’s life before.  This need to know this information can be daunting for a girl who is just trying to meet a nice guy and hopefully start a new relationship with someone.  But unfortunately, this kind of obsession can often be the quick start, and end, of dating.

For instance, I had just started dating this one guy, let’s call him “David,” and he knew that a couple months ago I had gotten out of a relationship with a guy named “Jake.”  He had asked if I had recently been dating anyone so I was honest and told him.  Now truthfully, I didn’t care if he had been dating someone last week.  He was dating me now and that should have been our focus.  But he cared.  Oh yes, he cared.  He wanted to know all about Jake.  How we met, where he was from, how long we dated, why we broke up, how I felt about it and then all of the little things in between.  And then after that q&a session was over, David would still bring up Jake at random times.  Like, “have you heard from Jake at all?”  “Do you still think about Jake?” or he would joke (I think) and say things like, “Oh, it’s because I’m not Jake.”  His obsession with whom I had dated last was annoying.  I wanted to focus on us and the beginning of our dating, but all he could do was focus on the past.  I believe that he wanted to see how he measured up to Jake, but I wouldn’t give him room to think about it.  I would answer very briefly, telling him, honestly, that I didn’t think about it anymore, and neither should he.  It was in the past, and I’m sure he had former girlfriends too, and it shouldn’t take up too much time of our thinking now.

What happens though if he does continue to dwell on the boyfriends of past?  It can happen.  Perhaps it is an insecurity he has and he needs to know what your other boyfriend was like so he can see a) what type of guys you date, b) what went wrong so he knows not to do that, or c) why you liked that guy so much and how he can amount to that.  He may think that he is asking all of these questions to better himself in the relationship, but what he doesn’t know is the stress that it causes you.  Maybe the breakup was bad, and you moved on from it, so him bringing it back to the forefront isn’t a good thing for you.  Or, maybe him bringing it up will remind you of your former boyfriend and make you want to get back together with him instead of your new dude.

So here’s what to do.  If he keeps questioning you incessantly about your former boyfriends, or even the guys that you have dated, keep it simple.  Try not to get wrapped up into all the explanations of your former boyfriends, because that will only stir the pot and make him want to know more.  Tell him that dating your other guy was right at the time, but things just didn’t work out, as relationships go.  So you’ve moved on, and you’re happy to be dating again.  Hopefully, he’ll get the point that you’re happy to be dating him.  If he doesn’t, just be blunt and say, “No more questions about who I’ve dated.  I’m dating you now, and that’s all that should matter.”  He should get the picture, and then after that, the only questions you should have to be answering are will be, “So, where do you want to go to dinner tonight?”


Dating Triumphs and Tragedies is published every Sunday by Online Dating Magazine columnist Nicole Roberge. She can be reached at

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