Prestige Monitor
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First-Date Conversation Topics: Best Worst, Politics, Religion, Marriage

A date once told me, "I'm sorry, I'm talking too much about myself!" But this is exactly the stuff I want to know: her job, her family, her friends, even the minutiae of her day. I almost feel cheated if I walk home from a date without learning much about her. Don't be afraid to open up.

DO: Talk about the future.

"I'd like to be married by the time I'm 30, and since it will take nine months to plan the wedding, that means I'll need to be engaged by May 1. That leaves eight months for a courtship. Can you pass the salt?" OK, so maybe not like that. But Future Talk doesn't have to be scary. You can drop hints. The stereotype, of course, is that men freak out when thinking about anything but the next 48 hours, beer, and football. Life is more nuanced than that, I promise. We're not all cavemen. If you're looking for a serious relationship, and if he too is looking for a serious relationship, then he wouldn't mind a glimpse—(just a glimpse, not a monologue)—of your mid- and long-term plans.

And the most controversial one…

DO (Carefully, gently, and in the right circumstance): Talk about babies.

This is just some real-talk. And it's context and age-specific. (It probably has less mileage for college students.) But now that I'm getting deeper in my thirties, I've been dating more women who, understandably, are no longer as easy-breezy about kids. As one mid-thirties friend of mine put it, "I'm just gonna start blurting it out on the first date. Because if he never wants kids, screw it." She's 100 percent right. And when women have broached the subject with me on a first date—using a light touch, of course—it didn't wig me out. I appreciated it. It let me know where she was coming from. Trust us to handle a dash of reality.

OK, all that said, I do have a few rules of my own:

1. No ex talk.

It's true that I think most dating rules are dumb. (And I'm a little biased, as I cowrote the book It's Okay to Sleep With Him on the First Date—and Every Other Rule of Dating, Debunked). But not all dating rules are foolish. There is absolutely ZERO reason to discuss exes on a first date. Ever. Unless, say, you have kids together. That deserves a mention. But otherwise? Just no.

2. Nix the complaining.

I'm guilty of this. If you get me talking about, say, Time Warner Cable, I'll spend two hours explaining why their incompetent, bewildering customer service must be managed by Hodor from Game of Thrones. But Negative Nelly is rarely a fun date.

3. Don't make it a job interview.

*A date is kind of like a job interview in that you're seeing if it's a good fit for both parties, but it's kind of not like a job interview, though, in that there's a chance that both parties will end up naked. So avoid the resume questions like "So what school did you go to?", "Where do you see yourself in five years", or "I see that there's a gap in your dating history. Please explain?" *4. Avoid loaded questions.