8 Questions You Should Ask A Guy On The First Date (But Probably Won’t)

While you don’t want to make things awkward by basically interviewing a guy on a first date, wouldn’t your love life be so much better if you could ask these important questions right away? If you’re feeling brave, maybe give one or two of them a try next time…

  1. Did your mom do everything for you growing up? This is important because a guy whose mom basically waited on him hand and foot growing up is likely going to be a bit useless as an adult. Unless he has the initiative to become a well-rounded adult on his own, a dude who can’t cook, never cleans, and basically does nothing because he expects you to come behind him to do it for him would be a terrible partner. Don’t even go there.
  2. How emotionally repressed are you? Perhaps this is worded a bit harshly, but you need to know whether or not you’re dating someone with the emotional range of a teaspoon, so to speak. If you want a healthy, thriving relationship, he needs to be able to voice his feelings and concerns so that you can work through issues together instead of letting them simmer until they explode.
  3. Can you handle not being the center of my universe? You’re a strong, independent woman with a full life. A boyfriend would add to your already full plate, not complete your existence. Because of this, you need someone who’s not going to be intimidated by the fact that you have lots of friends, passions, hobbies, and responsibilities outside of the relationship. If he gets jealous easily, give it a pass.
  4. How important is sex to you? You might be all hot and heavy in the beginning, but once the honeymoon phase is over and real life comes back into focus, there are going to be times when the bedroom action takes a back seat to everything else going on. Work stress, family drama, or any number of things could derail your sex life and you need to feel confident that he’d be cool with that and not go looking for it elsewhere in the meantime.
  5. Would you be intimidated by my guy friends? If you have guy friends in your life, you’re not going to give them up when you get a boyfriend (and you definitely shouldn’t). Your boyfriend needs to feel secure enough in himself and in your relationship to not pout, get aggressive, or try to convince you to drop the other men in your life to assuage his ego.
  6. What’s the real reason your last relationship ended? Sure, there’s the standard “we just weren’t compatible” schtick, which may be true enough, but the actual nitty gritty is likely a little more dramatic. Did he cheat? Did she? Did he get bored with her? Did he want to sow his wild oats? You should know what he considers to be deal breakers to determine your own compatibility.
  7. What are your opinions on abortion, immigration, and race? Again, this is heavy stuff for a first date, but these things matter. The last thing you want is to end up with a fake woke bro or worse, a hardcore conservative (unless you share the same opinions, of course). Getting your attitudes about the big issues out in the open early on will save you both a lot of time and potential animosity.
  8. Are you prepared for the responsibilities of being a boyfriend? Presumably, you’re ready to go all-in and work on being the best girlfriend ever but can he say the same? If he’s not ready to be a good partner, there’s no point in even dating him. Cut your losses, wish him the best, and move on to someone who’s on the same page.
Piper Ryan is a NYC-based writer and matchmaker who works to bring millennials who are sick of dating apps and the bar scene together in an organic and efficient way. To date, she's paired up more than 120 couples, many of whom have gone on to get married. Her work has been highlighted in The New York Times, Time Out New York, The Cut, and many more.

In addition to runnnig her own business, Piper is passionate about charity work, advocating for vulnerable women and children in her local area and across the country. She is currently working on her first book, a non-fiction collection of stories focusing on female empowerment.