Talking to your significant other about his ex-girlfriends

breaking up with your ex-girlfriendWhen two people start dating a little less casually (somewhere between “Go home, it’s getting late” and “Will you be my plus one”), they start to wonder about the other person’s past.

That’s when the ex questions usually come up. For women, sometimes our curiosity can get the best of us. What starts out as a few “I hope he’s not a man-whore” quality assurance questions can easily turn into a violent “tell me everything now!” interrogation.

But because we don’t want to scare him off (yet), most of us tuck that crazy back in and stick to the few basics:

  • What was your ex-girlfriend like?
  • When did you guys break up?
  • And why?

As detailed or as vague as their answers may be, we are content. That’s because any more probing could set off some “crazy bitch” bells, and we don’t want to ring those until much later in the relationship.

But when is it okay to ask more questions?

In my opinion there are 3 instances when it’s okay to dig a little deeper and not look like a loon.

  1. If he says, “I haven’t broken up with my ex yet.” At that point, you pretty much have free reign to ask him as many questions as you want.
  2. If he broke up with his ex just before seeing you. I’d say that merits a few more questions to get clarity on where he is mentally and emotionally, and what his intentions are.
  3. If his ex is somehow still in the picture. I can share from experience that constant phone calls from a bat shit crazy ex-girlfriend definitely raises some eyebrows.

relationships ex

What happens when it feels too late to ask?

Some couples have so much chemistry at the beginning that they tread into “let’s get serious” territory before asking the ex questions. One day, the woman realizes she has no idea where this guy’s been before he crawled into her bed. But because they’ve gotten serious already, it seems a little late to be asking those questions.

In this case, you really only have 2 options:

If you can’t stand not knowing anymore, just ask. There’s no “right time.” Just make sure he’s not shaving, slicing bread, or holding anything sharp before you hit him up with, “Hey, tell me about your ex!”

If you’re not sure you can handle knowing, it might be best to drop it. Otherwise, you could set yourself up to feel really “blah” about the relationship, which at that point you’re too invested to leave.

“How many people have you been with?”

Ahh, time to move on to the ever-popular and somewhat uncomfortable “magic number” question. I’ve heard mixed feedback on this topic. Some people MUST know the other person’s number before they even consider a second date. Others wait till they’re ready to sleep with the guy before they ask that question. And some NEVER ask.

I don’t think there’s a right or wrong approach here. You just have to do whatever you’re most comfortable with. Just be prepared for the answer. Sometimes their response can surprise you.

how many people have you slept with

Do the ex questions still come up after marriage?

I wouldn’t say the questions still come up (because at that point you pretty much know what you want to know), but sometimes the “blah” feelings associated with your partner’s ex can still arise. If a crazy ex pops her ugly head up from the dead, it would probably trigger some unpleasant feelings. Or if he and an ex casually decide to hang out, it can be a little uncomfortable.

I think all women have a degree of insecurity in them regardless of their relationship status – whether dating casually, dating seriously, common-lawed, engaged or married.

What a woman thinks when her man hangs out with an ex-girlfriend:

  • Dating casually: “Do whatever you want. I’m hanging out with other guys too.”
  • Dating semi-seriously: “I hope he doesn’t fall for her again.”
  • In a serious relationship: “If he cheats on me, I’m leaving.”
  • Common-lawed or married: “Mess around with her and I’ll go all Lorena Bobbitt on your balls! I dare you.”

crazy woman, don't mess with her, she'll kill you


Skip to comment form

  1. This subject is a minefield…I feel as though it is best left alone…unless it is really necessary, like if the ex is still around, then I do not think there is any need to ask the questions!!

    1. It can totally be a minefield, depending on what the ex situation is. Ex questions are usually loaded-gun questions, but some women just can’t help it. We ask even if we’re not sure we really want to know.

  2. Thanks for your insight into how to approach the (in many ways dreaded) ex situation. I totally agree that if you really want to know about the previous significant other that you need to be prepared -no matter what the response is. If you don’t think you can handle the answer, then I wouldn’t ask the question unless you want to open up pandora’s box!

    In many instances if you feel so strongly about your partner and see a future together you may have the view that the past is the past and there is no point going there!


    1. Thanks Catherine for stopping by and leaving a comment. Totally agree that it can be a totally awkward conversation to have and you have to be prepared for whatever you may hear. But if you really want to know, I guess you just have to be ready. 🙂

Leave a Reply

Your email address will not be published.

CommentLuv badge

This site uses Akismet to reduce spam. Learn how your comment data is processed.