That you're a 40-year-old virgin; that you're taking Viagra; that you played a major role in creating the sub-prime mortgage crisis: Hopefully, it's obvious that these are a few topics that would be best avoided on a first date. But perhaps there are some other matters that you're not so sure about. Like, do you talk about your ex? Your parents' divorce? Your joblessness? For the most part, I think if there's a questionable, uncomfortable or possibly contentious issue that's on your mind, remind yourself beforehand not to mention it--unless it's something that could be a deal-breaker. And unless it's something that could potentially make your date distrustful of you. Let's discuss, shall we?
Best to avoid most, if not all, talk of these puppies till date two or three, at the very least, if you ask me. Otherwise, your date's romantic fantasies about you and him might be overshadowed by images of that other dude whom you've described as someone you're "still not quite over." Even if you've been divorced--which, let's face it, is more and more common these days--I'd hold off on mentioning that, since it's no crime to postpone divulging the information. Unless, of course, you have kids from your earlier marriage, and they're a big part of your life. Since that's something that might be a deal-breaker, and understandably so, I'd communicate it early on, without letting it become the one-and-only thing you discuss.
Former non-relationships + other sexual exploits
If I had a dime for every time I screwed up a date by getting nervous, drinking too much, and then attempting to regale my date with stories of my wild childhood, growing up in Jersey as a repressed Catholic school-girl who would never have sex with anyone--but did give my fair share of back-seat blow-jobs ... ? Had I a dime for every time like that, I wouldn't be writing this blog--I'd be living in a mansion in Malibu, having servants fan me with Ecualyptus leaves, feed me grapes, and paint my toes. I seriously don't drink on first dates any more, mainly to save myself the embarrassment of saying wildly inappropriate things out of nervousness, idiocy, who know's what.
Similarly, I was recently at a lovely dinner party, where the lovely host--who'd invited someone she had a crush on and who'd perhaps had too much wine--told a story over dessert about how she'd recently had anal sex with a well-known visual artist. Yes. Despite the fact that I'd tried to stop her by jumping up, pretending I needed to grab something from the kitchen, while frantically making slice-my-throat gestures at her and cutting her off multiple times to re-fill wine glasses, offer around a plate of cookies, and ask if anyone wanted tea.
No one you are attempting to enamour wants to hear about your sex with other people! Save it for later ... much, much later.
Yes, formative experiences--like the death of a parent when you were young, or a big divorce that screwed up your adolescence--are an important part of who you are. But they can also be depressing. And if you carry on about them too soon, your date may think (perhaps not unfairly) you have some serious issues that you still need to work through.
See above. While I tend to think that just about every human being--including my dear Jonas Singer--could benefit from some time with a head-shrinker, it's not something you need to discuss straight away. Similarly: Avoid mention of any psychopharmaceutical drugs you might be taking.
Hmm, tricky. I think most people are going to be turned off to hear that you don't have a paying gig--and yet I think it will be hard to avoid discussing the issue on a first date. And while most people probably won't fault you for withholding information about, say, your mother who is in a mental institution during Hang-Out Session #1, failing to mention that you don't have a 9-to-5 seems closer to a lie. So mention it--but also emphasize how you're looking for something new, have some great prospects, and are feeling hopeful about the future. And if you got a hefty severance check, or have a nice cushy amount saved up in the bank, go ahead and throw that in there, too.
Credit card debt (and other financial problems)
Not so attractive. Avoid initially. And when you do bring it up, be sure to also talk about the plan you have to get yourself out of the hole.
My friends, what do you think? Agree, or disagree? What other topics should be assiduously avoided? What things must you tell on a first date, no matter how painful?