Guide to Asking Inappropriate Questions

19 04 2013
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A couple weeks ago, a discussion began in the comments section about the right time to ask inappropriate questions. And since then, I’ve been trying to come up with a better answer than – “not on the first date.”

The reason that answer is wrong is because nothing is ever black and white, so maybe the chemistry you and the other person have makes it okay to bring up what would normally be inappropriate dinner conversation. Maybe it’s you all’s first date, but you’ve known each other for years? Maybe the date lasts a whole day and then feels more like 3 dates in one than a typical first date. Heck, maaaaybe… you just like inappropriate questions and you’ve been waiting for someone to go there on a first date, to no avail!

So anyway, as you can see – I’m not a fan of making an absolute statement in this case (even though I really want to say “not on a first date”). I will say, though, that asking inappropriate questions is a little like the definition of porn. You may not be able to pinpoint exactly the best time, but if you’re sane, you’ll probably notice it when it happens.

Since I couldn’t pinpoint a guide of when to ask inappropriate questions, I figured the next best thing was when NOT to ask them. That’s more important anyway, right? If you miss the opportunity, that’s fine, it’ll come up again – but if you aim too soon? Chances are you won’t see that person in this lifetime or next.

Here’s a few questions I’d suggest asking yourself before just coming out and asking someone “what that mouf do, tho?”

Have you all spoken about under-the-surface topics before?
Meaning, if your conversations have thus far been all about the weather and your respective jobs, right now’s probably not the right time.

Does he or she seem the like the kind of person who would find it funny or get really, really offended?
Chances are if you don’t know the answer to this, it’s not the right time yet.

Have you kissed/made out/joked about making out before?
If not, pump those brakes brotha or sista!

Are you in public/could you potentially embarrass him or her with this question? Some folks are more willing to discuss inappropriate things in private than public, so loud-capping someone with a question about their freak status probably isn’t the way to go.

What do you all think? And have you ever experienced someone jumping way too soon into the inappropriate question arena? Funny enough, I think my friends and I are pretty inappropriate at times, and yet, I’d be willing to bet we’ve all had someone go too far too fast. Not sure why that is, but maybe these few questions will help stop at least one person from making that mistake again.




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