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The first date rule I always break

I’m generally a rule follower on the surface, but I do tend to rebel and chuck convention. In little ways. Pretty often. First dates are one of those times.

See, there are unwritten protocols about what you can and cannot talk about on Date #1. Usually, you are supposed to get the basics out of the way, and avoid talking about politics, religion… and past relationships. While I usually save the former two topics for later dates, I pretty much always broach past relationships right from the get-go.

Part of the reason? I hate small talk. Hate, hate, hate it. And small talk on first dates is the worst. You likely don’t know the guy, or barely know him, and you’re forced to volley unimportant topics back and forth until someone metaphorically cries uncle. No one cares what the weather is doing (I can see it), and no one wants to talk about the nuances of the food we’re eating (I can taste it). That’s just painful. I’d rather engage in some witty banter and real talk.

When you’re sitting there, on a date, feeling out whether or not there’s romantic potential seems like a natural thing to do. And the best way to feel out romantic potential is to figure out how your date views relationships in general and how he views his past relationships. Asking about his history accomplishes a few major things:

1. It shows a guy you’re fearless.

You break rules! Guys love that (wink, wink). It also releases some of that small-talk pressure from the male perspective. If you control the conversation in this area for a while, and seem genuinely interested in his thoughts on this off-limits topic, he doesn’t have to continually think of questions to ask you. Fact: Guys usually love talking about themselves, even if it’s about their former flames, as long as you’re not getting into the nitty-gritty deets of past relationships right away. Stick to mostly generalities.

2. You can find out if he’s still wounded.

Many times, you’ll figure out a guy is still hurting from a breakup. Let’s face it: Everyone has a first date after they split with an ex, and you could be it. No one wants to be the rebound girl, so you can proceed with caution until you figure out if he’s truly ready to pursue a new relationship.

3. You can find out if he’s toxic.

How a guy talks about his past relationships can give you a lot of information right off the bat. You don’t need to get hyper-specific, but if he’s immediately defensive or evasive about the basic reason his last relationship ended, it could mean he did something sketchy leading to its demise. And if every single one of his exes is “so crazy,” you can count that as a red flag right there. (Someone made them that way, my man, and the common denominator is you.)

For what it’s worth, asking this question has never stopped a guy from asking me out again. Like I said, they are generally more than willing to share. Just don’t slap them across the face with demanding probes into their personal lives. You are not the Spanish Inquisition. Lead into it softly. Saying something casual as the conversation is transitioning, like, “So, have you dated anyone recently?” That simple line usually does the trick. Trust me. Good guys are not afraid of this question.

So, next time you’re on a first date, go ahead. Be a rebel, ditch the small talk and get some real answers. (You can thank me later.)

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