First dates are the worst. Okay, that isn’t true; they can be fun and exciting, but also totally nerve wracking, from the time you accept the date down to just before it starts. And once you’re face to face with your companion, it can be hard to keep the conversation flowing without making things too stiff or formal like a job interview.
Luckily, we’ve prepped a list of interesting questions to ask your date sure to keep you chatting well into the night.
How did you choose this bar/restaurant/cafe?
There couldn’t be a more natural conversation starter to ease into the date. It opens up the opportunity for them to tell you whether it’s their neighborhood favorite, a new restaurant they wanted to try, or if it’s because of their extensive wine list. If it’s a favorite, you can ask them for drink or meal recommendations. If it’s a new restaurant for the both of you, you can bond over the experience.
What was your favorite TV show growing up?
This dating question is flawless, because the light and fun topic allows the two of you to reminisce about childhood favorites. People love nostalgic conversations, and with good reason. Nostalgia isn’t just an instant mood booster, but can also increase feelings of social connectedness.
What are your friends like?
Many people don’t think about their date’s friends until they meet the crew for the first time. Asking in advance about the people that he or she chooses to spend time with can reveal a lot about them. Is your date’s best friend their childhood neighbor? Then they likely value lasting relationships. Do they spend time with people from their local soccer league? Then they may be interested in meeting new people to try new things. Hearing about their social circle will answer questions that you may have without the pressure of issuing the third degree.
Who would play you in the movie of your life?
We have all fantasized about becoming famous, with the cherry on top being our own biopic, and we’ve definitely thought about who should play us. When your date tells you about which actor or actress should play them, you have the opportunity to probe into why, which can help you understand how they view themselves.
If money wasn’t an issue, what would you do with your life?
If you’re planning on investing time and emotions into forging a relationship with your date, don’t you want to know their dreams and aspirations? Even if the response seems completely unrealistic, it’ll give you great insight into their character, especially if they wow you with an answer like “raise the global standard of living.”
What’s on your bucket list?
Unlike the last question, this one is a bit more grounded in reality and can teach you about your date’s motivation. If they tell you that they want to make the Forbes 30 Under 30, then you know that they’re ambitious and goal-oriented. On the other hand, if they say that they don’t have anything on their checklist, make it their homework to come up with one for the second date.
Do you have any nicknames?
At one point or another we’ve all been given a nickname, so this one is pretty fail-safe. It’ll give you a peek into their lives and relationships with others, whether the nickname came from a family member, best friend, or colleague. It encourages sharing and continued conversation because they can’t just say that their nickname is “T-Bone” and leave it at that- you’ll have to press them for why!
What’s the craziest thing you’ve ever done?
This is an interesting icebreaker which gives you the opportunity to find out if your date is an extreme risk taker and rule breaker or more on the straight and narrow. You’ll either get a funny story out of their answer or end up hearing the details from their lengthy rap sheet. Want to avoid that possibility altogether? Run a people search prior to your meetup to learn more about him or her, including whether or not they have a criminal record.
If you could travel anywhere in the world, where would you go?
Maybe you and your date share a dream destination, or maybe they can introduce you to a place you’ve never heard of. Either way you’ll discover their appreciation and attitudes toward other cultures, traditions, religions, and cuisines.
Now that you’re armed with these dating questions you can relax a bit. Even if you start to blank on these talking points come date night, remember to ask questions other than those with simple yes or no answer. Keep questions open-ended so that your date has the opportunity to expand on their answers. Every conversation is two-sided, so be prepared for some of your questions to spur on some inquiries about yourself!
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