Besides the obvious “how much money do you make,” the one question you should never, ever ask on a first date is: “do you like kids?” Yes, I know it seems like a perfectly innocent question. But you ladies should know that it’s anything but that.

By asking this question, you’re basically communicating one of two things:

  1. For whatever reason you’re already thinking about children just minutes after we’ve met. I don’t know about you, but that’s a bit off-putting to me. It basically screams, “My biological clock is ticking!

  2. You’re a single mother who’s insecure about the fact that she’s a single mother. Honestly, most guys have no problems dating a single mother. But if she makes an issue out of it early and often, then yes, it does become an issue for us. That’s when we start asking ourselves, “Is she more interested in me or my potential ability to support her children?”

As long as you’re smart, sexy and confident, it really doesn’t matter to us whether you’re single or a single mother. So unless your ideal first date somehow involves an interrogation room, a polygraph machine, and Michael Jackson, please don’t bring up the subject of kids halfway into your appetizer.

Ron Lee, a.k.a. The Boston Bachelor, is the editor and writer of, a mens’ sports, relationship advice and entertainment magazine. He is currently working on his first non-fiction book Tech: What College Wasn’t Like for the Rest of Us. He is also in pre-production for his debut feature film FOBS, and currently resides in the Boston area