50 Non-Awkward Questions for a First Date That’ll Actually Spark a Connection

Jenna Ryu
·7 min read

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Meeting a potential partner should be exciting, but the nerves and pressure can easily make things…uncomfortable and intimidating. That’s where prepping a few questions for a first date can come in handy: A good one will prevent much-dreaded silence and maybe even spark some real chemistry.

“We ideally want conversations to flow organically,” Payal Patel, LMFT, licensed therapist and CEO of Manu Counseling in Montclair, New Jersey, tells SELF. But let’s be honest: You’re with a person you don’t know in an unfamiliar yet intimate setting, and the stress can be intense—especially when you’re worried about making a solid first impression or anticipating yet another dating horror story. Awkward silences are bound to happen, but Patel says the right icebreaker can ease some of that initial tension—and in a perfect world, eventually lead to smooth, engaging chats that feel organic, not scripted.

The trick, though, is striking the right balance: You want it to be a genuine exchange, not a pre-planned job interview. What makes a “great” conversation starter depends on your dynamic—something Patel says you’ll likely have to feel out as the date unfolds. For example, “some couples are open to deep and intimate questions about their past relationships or future together, while others aren’t comfortable with those types of discussions so early on,” she explains. Not to mention, asking about marriage right off the bat might be a bit much for a person who’s just looking to have a good time.

So if you’re hoping to skip the cliché small talk (Where do you live? What do you do for work? Tell me your life story) and actually build a real connection, here are a few expert-approved options to help you break the ice—and see if there’s potential for a second date.

First, what makes a “good” conversation starter?

No matter the topic, what’s important is that your conversation starters actually, well, lead to conversations. For that reason, Rachel Zar, PhD, LMFT, AASECT-certified sex therapist at Avid Intimacy in Chicago, tells SELF that it’s best to stick with open-ended questions that’ll invite more than just a one-word response. Instead of saying, “Do you want kids?” for instance, try, “How do you feel about having kids?” The latter opens the door to a real discussion rather than a potential dead end.

It also helps to lean into things you know they’re into, Dr. Zar adds. Depending on how you connected, you probably already have a little background like the job they’ve had for five years, say, or their pets all over their dating profile. “People love talking about themselves, and they’ll light up when you mention things they’re passionate about,” she says.

However, conversations are a two-way street—meaning, even if you come up with the most thought-provoking questions, it doesn’t mean much if you’re not actively contributing. Chances are, they’ll probably ask a few predictable basics—how your day was, what your hobbies include, etc. In that case, Dr. Zar says “it can take the edge off to have a story or two ready about something that happened to you this week, or a personal interest you’re excited to talk about.” That way, you’re not left drawing a blank and adding to any awkward vibes.

On that note, there aren’t necessarily “wrong” things to ask on a first date either. As a general rule of thumb, “I’d avoid yes or no questions,” Karyna Auletta, LMFT, licensed psychotherapist based in Los Angeles, tells SELF. “Also, make sure you’re not asking something you yourself aren’t comfortable answering.” So if the thought of being grilled about your exes makes you squirm, maybe hold off about prying into their recent breakups.

Also, your listening skills are just as important as your questions, according to Dr. Zar—they make a conversation feel authentic, not rehearsed, and help you come up with natural follow-ups. (Oh, you like pop music? Who’s your favorite artist? Have you been to any of their concerts? Oh, me? I’m obsessed with Lady Gaga.)

Ultimately, though, what kinds of topics for a first date feel “right” depend on your unique vibe. Below, we’ve rounded up a bunch of ideas to get you started, whether you’re looking to get deep or just have a little flirty fun.

If you want to start off light and casual

1. What were you doing before this date?
2. What’s been the highlight of your week so far?
3. What’s your go-to order at a place like this?
4. How do you spend a typical week?
5. What do you usually do in your free time?
6. What are some hobbies you’ve been wanting to learn or get better at?
7. What’s your all-time favorite [book, movie, show, game, etc.]?
8. Do you like to travel? What has been your favorite place so far—or what’s on your wish list?
9. What type of music do you usually listen to?
10. How long have you lived in _____? Would you ever consider leaving?
11. If you could trade lives with anyone for a day, who would it be and why?
12. Who do you usually call when you’re having a bad day?
13. What’s the most random thing on your bucket list?
14. How do you feel about social media? Do you have a favorite app?

If you’re looking to learn more about them—without overstepping

15. Are you more of a texter or a caller?
16. How would your closest friends describe you?
17. Among your friends, what are you best known for?
18. Who is the person you look up to the most?
19. What’s something you wish more people knew about you?
20. Did you set any goals this year? What were they?
21. What’s one thing you hope to accomplish in the next five years?
22. What’s something you do every single day without fail?
23. How do you feel about your current job? If money weren’t a factor, would you pursue anything else?
24. What’s one topic you could make a whole TedTalk about?
25. What’s your biggest pet peeve?
26. Do you tend to be more of a planner or more spontaneous?
27. What’s one thing you really value in your friendships?
28. What are your hidden talents?
29. What are some accomplishments you’re really proud of?
30. If you could have any superpower, what would it be?
31. What wrong assumptions do people make about you?
32. Is there anything in your life that you feel like you’re missing—like a specific achievement or experience?
33. Who’s the person you talk to most in your life?
34. What’s one thing you’re always willing to splurge on?

If you’re ready to suss out your compatibility

35. What made you want to go on this date with me?
36. What was your first impression of me?
37. I really care about _____. What about you?
38. What’s one date idea you’ve always wanted to do?
39. What are some of your favorite romantic gestures?
40. What are you looking for right now? Something casual? Long-term?
41. What are some of your dealbreakers or pet peeves while dating?
42. How do you handle conflict? Are you usually more upfront or go-with-the-flow?
43. What’s your love language?
44. How long was your most serious relationship?
45. What are some nonnegotiable things you’d like in an ideal partner?
46. What are the most attractive qualities to you in a partner?
47. How do you prefer to spend quality time together in a relationship?
48. In your opinion, what are the most important factors in a successful relationship?
49. What’s the best piece of relationship advice you’ve ever gotten?
50. What’s the biggest lesson you learned from your last relationship?

Beyond what topics you lead with, Auletta says what’s most important is showing up as your true, authentic self. In other words, “don’t pretend to be someone you’re not, or ask certain questions for a first date that feel unnatural or uncomfortable to you,” she says. Genuine connections happen when you’re honest, curious, and engaged—and before you know it, the conversation will flow so easily, you ideally won’t even need to lean on this list.

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Originally Appeared on Self

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