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Awkward first date? These 15 fun questions will change that

Let’s be honest: First dates, while exciting, can also be downright terrifying. Sometimes we get so caught up in what a first date can lead to that we freeze under the pressure. Awkward silences abound, or worse: You ask him a question that either comes off like you’re interviewing him for a job, or you’re interviewing him for the wedding you already have planned. Either way, womp, womp.

Because there will be times when you’d like a second date, let’s learn the art of asking your potential guy the right questions, shall we?

You should use this time together to playfully grill each other — while, you know, throwing in some flirting for good measure. Asking questions is also a great way to calm your nerves: “This takes the attention off you so you can take a few deep breaths and calm yourself,” says relationship expert Nicole McCance. “Pick something you have in common, whether it’s a mutual friend, the bar you met at or the online dating site he emailed you on and go from there.”

The more you allow questions to come up naturally as you go along, the easier he’ll feel you are to talk to. “The secret to achieving good flow is to intersperse the question-asking with tidbits of sharing about yourself, and when you do ask further questions they should be related to new information that he’s just revealed,” says relationship expert Kimberly Moffit.


You: “Where did you go to school?”

Him: “I went to Queens. I’m originally from Kingston, so I wanted to stay close to home.”

You (Right way to achieve conversation): “Oh, that’s cool. I have a couple of friends who went to Queens and they loved it! So what was it like growing up in Kingston?”

You (Instant conversation-killer): “Oh, OK. So what do you do for a living?”

You want to try to incorporate your questions throughout the flow of the conversation, not as if you’re checking them off a list. “If you pose a question that elicits the same information as a joke, a clause in a humorous story or wrapped in flirtation, you may not only get your answer, but you’ll open a conversation about the topic,” says relationship expert April Masini.

15 Questions to ask on a first date

Shoot for questions that take the two of you off the beaten path, for example:

1. “This cocktail (pizza, latte, etc.) reminds me of Portugal. I don’t know why — I haven’t been there since my junior year abroad. Do you ever have that, where something normal reminds you of your past?”

This style of question can take the two of you anywhere. If anything, seeing where he goes with it will be more interesting than the actual answer!

2. “Whatever happened to those great double features? What’s the most number of movies you’ve ever seen in one day?”

This type of question gives him information about you first, so it comes off less like a job interview and more like you’re opening up to him. By then asking him an offbeat, lighthearted question about his past, you’re inviting him to do the same, but giving him the opportunity to take the conversation wherever he wants.

3. “That scene in [ movie you’ve both seen ] where they were swimming at night in the ocean — reminded me of skinny dipping at camp as a kid. I really miss that kind of thing. Did you ever do things like that?”

This is a risqué question wrapped in an anecdote wrapped in a flirt. “Simply wrapping risqué content into charming memories makes it fun conversation fodder, and a way to get to know him beyond the dinner and a movie date,” says Masini.

If your motto is “always be prepared” and you just have to memorize as many questions as possible, make sure they’re versatile questions you can pop into the conversation at a moment’s notice:

4. “How did you end up in [ insert city here ]?”

5. “Where are your favorite places to go out?”

6. “What was it like growing up with three sisters?”

7. “What’s your all-time favorite food?”

8. “Where have you always wanted to travel?”

9. “What was your worst job?”

10. “What are your biggest pet peeves?”

(And hopefully you haven’t done any of them.)

11. “What’s the best advice anyone’s ever given you?”

12. “Where would you want to travel if you could?”

13. “What do you like to do in your spare time?”

14. “Are you a morning person or a night person?”

(If he’s a morning person… well, have fun with that.)

15. “What was the worst first date you’ve ever been on?”

(C’mon. Live a little.)

Topics to avoid

Steer clear of history conversations, such as ex-girlfriends, and future conversations, such as what he’s looking for in a mate. Stay completely in the present moment, and you know, take a chill pill. “Most men feel like they’re being interrogated during the first date, so try not to grill him with heavy future-oriented questions,” says McCance. “Even if you’re dying to know, let it flow naturally. Men don’t like to feel pressure, and they can smell it a mile away.”

More first date tips

25 Topics to never bring up on a first date
Survey says sex on the first date isn’t as bad as we think
What he wants most on the first date (it’s not sex)

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