Unless he asks, and even then, talking about your ex on a date can lead to a disaster. If you've only been out a handful of times, a penchant to talk about a recent breakup makes it seem like you're stuck in the past and not ready to move on. And if he feels like you're not quite over your ex, he may feel like a rebound guy, which some guys are OK with, but some won't want any part of it.
If you find yourself tempted to bash your ex in front of your date, stop yourself. Trick yourself by talking about other people's exes - do you have friends who've been through particularly brutal break ups? We're not suggesting you air other people's dirty laundry, especially other people he might meet (if things go well), but you can ask him what he thinks about various (totally anonymous) situations. Chances are his own share of buddies are dealing with similar situtations - in which case you can bond over other people's break ups, rather than discussing your own!
You may be very tempted to find out everything you can about his last lady love, but try not to ask too many questions. You don't want to come across as overly jealous or insecure so avoid starting a question and answer period about his ex. If and when the relationship progresses, and he feels comfortable discussing his past, then you might be able to get some answers, but for now, keep the past girlfriend curiosities to yourself.
The only tip we have: Just DON'T do it. Seriously, unless you've been dating for a while (as in longer than 6 months) don't make a habit of digging for info about his romantic history. It will just make you sound posessive and insecure - never good traints in a girlfriend.
There is nothing less sexy than someone droning on about the size of their thighs or how they should never have ordered dessert (for fear of it going right to their thighs). Project confidence rather than showcase all your body hang-ups in order to keep him interested. If he's out with you, he probably thinks you're attractive. Don't give him reason to think otherwise.
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