6 Interesting Questions to Help Get a First Date Started

A couple walking down the street during a first date and laughing.

If you’re a dating app veteran, you know how it goes. You match with a cutie, exchange a few messages to make sure you guys vibe, and then go out for drinks or dinner.These early message exchanges and first dates generally consist of the same basic questions:

What do you do?
Where are you from?
What part of town do you live in?
Where did you go to college?

While there’s nothing wrong with these questions, they don’t exactly make for the most enthralling conversation. And once you’ve been on a decent amount of dates, they all start blending in to each other—because you end up talking about the same things on most of them.

But sometimes it’s hard to stray away from the same old topics, especially when you’re just getting to know someone. But small talk should be saved for networking events and family reunions with far-removed relatives, not a potential partner.

Here are six interesting questions to get a first date off to a good start without putting your partner completely on the spot—or coming completely from left field.

1. What was your last relationship like?
Let’s start off the bat with a doozy! Just kidding, this shouldn’t be a doozy. And if it is, you may reconsider if you’re ready to date and/or if your date is bringing a lot of baggage to the table.

There’s a negative stereotype about people who bring up their exes on dates. While there’s definitely a wrong way to do this, I also think you should absolutely want to know about a potential partner’s relationship experience before diving in head first. You can learn a lot about someone by the way they talk about their past partners.

This also sets you up for open communication in your relationship. It’s okay to acknowledge that you’ve both been with other people before—you’re adults, after all.

2. What do you like to do when you’re not working?
We always ask each other what we do for work, but we less often ask others what they do for fun.

Personally, I never know how to answer this question because I’m a work-a-holic, but this question is definitely more interesting than the classic, “What do you do?” (which is usually already listed on their profile) and can lead into conversations about exercise, television, food, music, and more.

3. What was the last book/TV show/movie you really got into?
This is still a pretty basic question—especially if you choose to go the TV route, but it tells you something interesting about your date if they’re willing to explain why they liked the book/TV show/movie so much. It also lets you know if your date is more of a Netflix-binger or a bookworm, and what kind of movie to choose if you plan on going out again.

4. What’s your zodiac sign?
I love when zodiac signs get brought up on a date (and in LA, they almost always do). You don’t have to believe in horoscopes to want to bring them up on a first date. Not only does it tell you when your date’s birthday is, it can also tell you if they believe in the zodiac.

A good follow up question to this one is, “Do you feel that you possess a lot of the characteristics typical of your sign?”

Of course, if neither of you know anything about zodiac signs, this might not be such a great question—but hey, maybe you can both bond about how you think horoscopes are silly? Or you can Google your sign’s compatibility and find out you’re meant to be?

5. What’s something that you feel like gets better as you get older?
One of the common questions or topics that gets brought up on a date is your age. Whether your date is older, younger, or the same age as you, this is a fun follow up question that won’t seem totally random. Maybe their answer will be sex, maybe it will be that they now enjoy staying in on Friday nights. Whatever it is, chances are you’ll learn something about them and be able to teach them something about yourself with your response.

6. What wrong assumptions do people tend to make about you?
If you use dating apps, chances are you make assumptions about people all the time. Whether they’re positive (“he has a lot of pictures with children, so he must be a good guy”) or negative (“she has a lot of bikini photos, so she’s probably just looking for attention”), we all do it—even if it’s subconscious.

This is a great question to ask your date because you give them a chance to defend themselves from the stereotypes that people project onto them—stereotypes that you, too, might have made about them when agreeing to go out with them.

I feel like many of us worry about getting too personal on first dates—but considering that most of us are looking for a potential partner (whether long-term or simply sexually)—the more personal the questions, the better (within reason, of course). Try some of these questions on your next date and see if your date stands out more than the last five people you went out with, I dare you.

Ashley Uzer

Ashley Uzer is a freelance writer who specializes in sex and dating. She has written for many international outlets including Bustle, VICE, & Galore. She’s currently doing the whole digital nomad thing, but you can find her in Washington D.C. or NYC every once in a while. Follow along with her adventures on TwitterInstagram, or on her blog.

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