10 Inappropriate Questions We Wish We Could Ask On The First Date

10 Inappropriate Questions We Wish We Could Ask On The First Date ©iStock/gilaxia

First dates are just like job interviews. We have to ask the right questions and make sure the guy isn’t a psychopath or a stage-five clinger. However, there is still some first date etiquette that we should abide by. Unfortunately, there are also certain questions that we want to get answers for, but it’s way too soon to ask. Truly getting to know someone takes time, but some things are better to find out sooner rather than later. If tact wasn’t a thing, however, here’s what we’d ask.

  1. So, are you paying, am I paying, or are we going dutch? How are we doing this? If we’re out to dinner, we always have to do our female due diligence of reaching for our wallet on the first date, but we never know what will happen next. He may a completely gentlemen and pay for the bill or he may pull the “forgot my wallet” line. We’ll find out at the end of the date, but it’s something we’re definitely thinking about in the beginning.
  2. What’s your number? Always the scariest thought. Some couples go throughout their entire relationships without ever knowing their partner’s, which is completely understandable. It could either be very low or very high, but once you know, there’s no way of un-knowing.
  3. Do you or have you ever had and STD? A completely valid question, because safety comes first, right? You may like him, but not enough to contract an STD. Better to be safe than sorry.
  4. Are you only on this date to get laid? We’re all always curious about intentions, especially if we met the guy on a dating site or social media. Motives are always tough to tell these days, and unfortunately, many guys (and girls) are only interested in that one thing.
  5. When was the last time you had sex? Did he just come from another date? Did another girl sleep over the night before and I’m in the midst of being his next home-run?
  6. Are you actually interested in seriously dating someone right now? Some people date for fun and some people really are looking for love, but you never know. You could be on two opposite wavelengths, but it’s always nice to be on the same page even if they’re not “The One”.
  7. Have you ever been arrested? Criminal charges are definitely a red flag and probably a deal breaker. If this guy has done some jail time, then this is something we need to know and if it’s a serious crime, you should probably call a cab ASAP.
  8. How many people are you currently dating? These days, everyone is dating everyone. I don’t know what ever happened to monogamy, but it’s definitely not a common thing anymore. It’s a small world and that other girl could very well be someone who works at your company or even your roommate.
  9. How many people are you currently having sex with? Maybe he’s not dating other people, but he may be hooking up with multiple partners and you’re just another addition to his list of booty calls.
  10. You don’t have any weird fetishes or hobbies, right? I mean, after Fifty Shades of Grey, we kind of have to ask…
Lindsey is a Digital Advertising Professional and Freelance Writer based in New York City. In her spare time, she enjoys running, traveling, and drinking ridiculous amounts of coffee. Follow her on Twitter @lindseyruns