You already know what not to order, what not to drink, which shoes not to wear and the handbags not to carry on your initial date with a new guy. But, what will you talk about with your Mr. Right Now? Hopefully, it's obvious that there are a few no-no topics on a first date. But perhaps there are some matters that you're not so sure about. As a rule of thumb, if there's a questionable or uncomfortable issue that's on your mind, remind yourself not to mention it, unless it's a deal-breaker in your book.
Past Relationships. Best to avoid most, if not all, talk of past boyfriends until at least date number three. The last thing you want is for your new crush to think you’re not over your ex.
Former almost-relationships (and other sexual exploits). Just because you’ve spent a few years as a Samantha in and out of beds all over Manhattan, you’re new love interest doesn’t need to hear about your less-than-classy past. Tales of one night stands and walks of shame may make your girlfriends laugh, but a new guy may be turned off by stories of random romps.
Your Not-So-Perfect Childhood. Experiences like the death of a parent when you were young or a divorce that seemed to screw up your pre-teen years are important clues to who you are, but they are depressing topics to share with someone who knows nothing else about you. If you carry on about your tough childhood too soon, your date may think you have serious issues that you still need to work through.
Your Therapist. Most people could benefit from some time with a shrink (and hell, in NYC it’s a luxury to have a weekly therapist appointment), but it's not something you need to discuss on day one. Also, avoid mentioning any psycho-pharmaceutical drugs you may be prescribed.
Joblessness. Many men (and women) are turned off to hear that you don't have a paying gig, yet it’s hard to avoid answering the “what do you do?” question on a first date. You can mention your unemployment, but make sure to include how you're actively looking for something new, have some great prospects or interviews coming up and are feeling hopeful about the future. Being optimistic about your career, among other aspects of your life, is attractive, despite a less-than-perfect current situation.
Financial Problems. Avoid discussing your credit card debt, student loans and inability to pay your rent next month, until you’re in a relationship. Once you do bring it up, be sure to talk about the plan you have to get yourself out of debt.