- WHAT SUPERPOWER WOULD YOU LOVE TO HAVE?
This is a great ice breaker question on dates. It will also sneakily show you where a guy’s at and if he has an imagination. The last thing you want is to be with someone who shuts you down when you dream or are creative, but have fun with this one.
- WHAT DO YOU ENJOY ABOUT YOUR JOB?
If you ask this and he doesn’t care about his job or career, and he’s not ambitious in the least, that’s a huge red flag. You don’t want to date someone who doesn’t have a goal for his future.
- WHAT DO YOU LIKE MOST ABOUT RELATIONSHIPS?
This is a toned-down version of asking the guy what he wants out of a relationship. You’ll be able to gauge what makes him excited about relationships. Obvs, if he writes off relationships or tells you straight up that they’re not really his thing RN, run.
- WHAT’S SOMETHING MOST PEOPLE DON’T KNOW ABOUT YOU?
Is he a strong guy who’s got a really soft side? Awww. Is he a guy who loves to shoplift on the weekends? Yikes. Ask this question to make him think and so that you can suss out where he’s at and what he’s really like.
- WHAT WAS YOUR EX LIKE?
This might be too much to ask on a first date, but if exes have come up you can ask what his ex was like. If he says she was crazy, that should ring a warning bell. But this question also helps you to ask other questions about his relationship history, such as how long, exactly, he’s been flying solo.
- WHAT’S THE BEST THING TO DO WHEN YOU HAVE SPARE TIME?
This will show you what’s important to him and how he spends his days, like what hobbies and interests he has. It can save you time because if he tells you that he just wants to hang with his best mates and drink ‘til he blacks out, you can find out immediately that you’re not on the same page. Ugh.
- WHAT WOULD YOU TELL YOURSELF AS A TEENAGER?
This is a good question to ask the guy on a first date. We’ve all made mistakes in the past, so this question will help you to learn more about what he’s done, how he’s improved in his life, and what he regrets. Deep stuff but without sounding too heavy when asked over cocktails.
- WHAT MAKES YOU REALLY ANGRY?
You don’t want to date a guy who’s got a violent temper or anger issues, so asking this can help you figure out if he’s boyfriend material. If he says, “Man, what don’t I get angry about, you know?” cut the date short! This is one of the questions to ask guys to figure out his general temperament, which is super important.
- IS TEXTING IMPORTANT IN A RELATIONSHIP?
You want to date someone who’s on the same page when it comes to texting, and you want textual chemistry. If he never likes to text, it helps to know that right away so you can see if you can deal with it.
- WHAT’S YOUR DEALBREAKER?
You should know your relationship dealbreakers. If the guy doesn’t have any, that should be a red flag. You can also tell a lot about him by his dealbreakers. Is cheating a dealbreaker for you but not for him? That’s info you should know right off the bat before getting into a relationship with someone!
- DO YOU WANT TO BE FAMOUS, AND WHY?
This is one of the most fun questions to ask guys, but it’s also quite deep. His answer will tell you if he loves having all the attention or if he’s a wallflower. You’ll be able to tell if you’re a good match when it comes to whether you’re an extrovert or an introvert.
- DO YOU HAVE A ROOMMATE?
While this might not seem immediately relevant, this is one of those questions you need to ask guys because they mean something for your long-term potential. You should find out who he lives with or if he lives alone. This question could also give you some funny stories about his roommates, so it’s a great way to start a conversation. If his roomie is his ex-girlfriend, that’s a red flag.
- HOW DO YOU DEAL WITH NEGATIVE FEELINGS?
Again, this is one of those questions that exposes how guys operate when it comes to conflict. This might feel too heavy, so save it for the middle of the date when you guys are in your conversational stride. If he says he hits the gym hard or goes on a hike, that’s awesome. It’s not so cool if he turns to substances to cover up all his bad feelings.
- HOW DO YOU APPROACH WOMEN?
Does he use lame pick-up lines? Or, does he try to form a real connection with someone? This could also give you some insight into if he’s still dating or hitting on women on dating apps. Hey, it’s good to know, right?
- WHAT’S YOUR FIGHTING STYLE?
Does he say he’ll do anything to avoid an argument, or does he have the bad habit of raising his voice during an argument with a GF? People who are dating need to get in sync with their fighting styles to prevent toxic arguments from happening. Again, this info is useful to know about and can reveal a lot about him.