Never Feel Weird About Asking These 10 Questions On A First Date

First dates are fun, sure, but they can be nerve-wracking. You may wonder what’s okay to ask and what’s probably off-limits and will make you seem like a psycho. Don’t stress too much! Here are 10 questions you should totally get the answers to so that you know what you’re in for and that you’re not wasting your time.

  1. What are you looking for? This may be the biggest question there is! Many people are afraid to ask this on the first date or think it’s too soon, but it’s totally valid to want to know what your date is looking for. If one of you wants casual and one of you wants serious then there’s really no point in going on another date, so it’s better to find out sooner rather than later.
  2. What’s something I should know about you? This is kind of a vague question, but most people can come up with an answer for it. They may say something that you’ve already learned from their profile or they may surprise you and say something completely out of the blue like that they’re a stand-up comedian. Be sure to have your own answer prepared because once they’re done answering the question, they’ll likely want to know about you!
  3. What’s your take on [insert deal breaker]? We all have our dealbreakers (or you should). They’re the non-negotiables that just absolutely won’t work for us in a relationship. It’s good to bring these up early on to find out sooner rather than later if someone’s going to have a deal breaker. One example could be that you don’t want to date a partner who smokes weed. It’s totally fine to bring that right up on a first date. If you’re incompatible in this way, you’ll find out ASAP.
  4. What are your political leanings? Especially if politics are important to you, this is a valid question. It might be a total turnoff to you if the person is of opposite political belief than you. Alternatively, if you discover you have similar values then you just opened a treasure trove of things to talk about! For some people, politics aren’t a make-it-or-break-it, but it’s still cool to know.
  5. What was your worst first date? This is just kind of a funny question where you can swap ridiculous stories if you have them. Their answer will shed some light on what they perceive as weird or bad in a date, so you’ll definitely learn something, too. Plus, you can give them that same opportunity when you tell your story, they’ll learn about what gets under your skin.
  6. What do you do? I kind of hate this question, but also it’s one of the only ways you can ask what they do for work in a straightforward way. So, it’s a valid ask. You’ll learn about their job and you can ask further probing questions to keep learning more about it.
  7. Are you happy with your job? This may seem like a bold question, but it’s a good one. You might think it’s super cool that they’re a teacher, but they could really hate it or feel like they should be doing something else. You just never know, so it’s totally worth asking. Again, you’ll have to have your own answer ready about whether or not you’re happy at work!
  8. Are you an introvert or an extrovert? This may or may not affect compatibility. Maybe you’re an introvert and you’ve had the experience that you really pair best with another introvert. Most likely, though, it doesn’t matter and you’re just curious to learn more about their style of living. This will provide insight into what their social life might be like.
  9. How do you spend your time when you’re not at work? It’s sexy when someone has hobbies. It means they’re being true to themselves and exploring what’s important to them. This can be a great way to get to know what someone values. Plus, it’s a low-pressure question. They don’t have to get super personal, they can just tell you they like to play soccer and read books.
  10. What are you watching on Netflix right now? This is a fun question. Who isn’t watching something on Netflix, Hulu, etc. at any given time? You can learn about their areas of interest, like if they’re into superhero stuff. This can give you an opportunity to check out some of the shows they’re into to see what they’re like. You can even swap show ideas. It’s just a nice, lighthearted conversation to have. All of the questions can’t be serious!
Ginelle has been writing professionally for more than six years and has a bachelor’s degree in digital marketing & design. Her writing has appeared on Birdie, Thought Catalog, Tiny Buddha and more. You can follow her on Instagram @ginelletesta, via her Facebook page, or through her website at