10 Questions To Ask A Guy On The First Date To Break The Ice

There’s nothing quite as exciting–or as nerve-wracking–as a first date. You’ve already decided what to wear, where to go and maybe even what to order, but you’re likely wondering how to keep the conversation flowing as freely as those cocktails. Come prepared with some classic and creative conversation topics. Here are 10 questions to ask your date to break the ice.

  1. What do you do for a living? Although not the sexiest question, asking about a guy’s job is an easy way to get him to open up early in the evening. After all, people love talking about themselves and this particular question allows for follow-ups like “How long have you been doing this?”, “Do you enjoy what you do?”, or “Do you get the opportunity to travel for your work?”. His response might also give you a hint as to his availability during the week. Does he tend to work late or get off in time for happy hour?
  2. What’s your favorite food? This is a logical question to ask if you’re meeting at a bar or restaurant and learning what kind of food he’s into might tip you off as to what future dates will look like. Is he talented in the kitchen (*swoon*) or is he more of a take-out kind of guy (no judging!)? Is he as crazy about Mexican food as you are or would he opt for a burger and fries? If you’re getting good vibes from the start, this could be the moment to mention any restaurants you know of that serve the food he likes.
  3. Where did you grow up? If you don’t know your date’s hometown already, this question is another softball to toss his way. If he’s from the area, he might be up to showing you around his old stomping grounds. If not, this is the perfect opportunity to offer to give him a tour of your favorite spots in town. His response may lead to talking about family or his childhood friends, people you’ll likely meet if this first date goes well.
  4. What were you like in high school? After learning where he’s from, asking about his high school identity is a fun segue into more personal questions. Was he on a sports team or in the drama club? A bookworm or the Prom King? Would you two have dated back then? This question also gives both of you the chance to share hilarious or cringe-worthy anecdotes about your teenage years.
  5. Where was your most memorable trip? Whether his job has him on the road or he’s taken to satisfying his own wanderlust, you can learn a lot about a guy from his travel habits. Would he rather fly to Europe or hike through a National Park? This is another subtle way to gauge his interests and your compatibility together. Who knows? You two might even share a bucket list destination.
  6. What’s your Netflix guilty pleasure? The date is well underway and it’s time to ask the big questions. Is he a Friends fanatic or is Breaking Bad more his speed? And has he seen Tiger King? His response might reveal you two share favorite series or suggest the chance to binge something new together. If Netflix and chill is in your future, it’s best to know what’s in his queue.
  7. What’s the best concert you’ve ever been to? Asking him to recall a favorite band or song might be a little intimidating, but this is an easy question to get to know his musical tastes and, consequently, even more about his personality. Find out if you’re dating a quiet, sensitive guy or someone who’d rather jam out to heavy metal. Better yet, his response may be an easy transition into future date ideas.
  8. What does your perfect day look like? Another way of asking about his hobbies, this question encourages your date to get creative about what he’d do with 24 hours to spend as he pleases. His response will clue you in on his interests, priorities, and what activities he’d potentially do with a partner. If he’s as charming as he looks, he’ll likely include a date with you in this fantasy.
  9. What’s your biggest pet peeve? If you’re seated next to someone smacking chewing gum or glued to their phone at the table, this question might come up naturally. While your date may give you a serious or humorous response, what he says could tip you off to any deal-breakers on his end.
  10. If you could have dinner with any person–living or dead–who would it be? Present company excluded, of course. He might choose a celebrity crush, favorite author, or a member of the Beatles. In any case, he’ll likely name someone he admires. Have him explain why and, of course, be sure to have your own response at the ready.
Julia is a recent graduate of the University of Virginia where she majored in English and French language and literature. She's engaged in an on-again-off-again French love affair (with the country itself) and has been crushing on French pop star Jean-Baptiste Maunier for about 8 years. When she's not writing you can find her rereading The Wizard of Oz or trying to run away with the circus.