No secret here—dating can be a real pain. Nothing’s more nerve-wracking than a first date, especially with someone you hardly know. And while, sure, dates are meant to be a precursor to an actual relationship, first dates are also mini-interviews disguised as social outings, whether we like to admit it or not. That’s why figuring out what to talk about ahead of time with a list of good first date questions and conversation starters is so important.

A foolproof way to ensure that conversation will always be flowing is to simply ask your date things, although—given the fact that we never know how comfortable others are with casual conversation—that might be easier said than done. The trick to successfully vetting a prospect on a first date, while simultaneously keeping the energy light and fun, is knowing what questions to ask and how to ask them. For example, work, his or her family, hobbies, pop culture, and favorite music are all surefire bets.

If you’re savvy, you’ll realize that certain questions–even the most basic ones—have the ability to tell a lot about a person. Here, we’ve divided your hypothetical first date into five phases and suggested a series of questions to ask your date during each.

“Ideally, first dates should strike a balance between lighthearted curiosity and deeper connection,” says Jordanne Sculler, LMHC, a licensed therapist for couples. The best questions will help you understand someone’s values, interests, and emotional depth, without making it feel like a formal interview or deposition.”

“The most important thing is to just be yourself—if you lead with authenticity, you’ll be more likely to attract the right match,” she adds.

What Not to Talk About During a First Date

There are some topics that probably shouldn’t be mentioned on the first date. “The key is to keep it light but intentional,” says Sabrina Bendory, dating expert for Dating.com. “You’re gathering information without making it feel like a checklist. The best connections happen when two people naturally fall into conversation that feels both exciting and effortless.”

Bendory suggests avoiding these topics on a first date for these reasons:

• Finances & Salary: “Talking about money too soon can feel transactional and create unnecessary pressure. It’s fine to discuss career ambitions and passions, but avoid prying into financial details.”
• Marriage & Kids (In a High-Stakes Way): “It’s okay to discuss long-term values, but grilling someone about their five-year marriage plan on a first date can feel overwhelming. Instead, keep it light with a question like, “What’s something exciting you’re working toward in your life right now?”
• Deep-Seated Trauma or Emotional Baggage: “Vulnerability is important in relationships, but unloading personal trauma or past heartbreak too early can create an imbalance. Save the deeper emotional conversations for when you’ve built more trust.”
• Highly Controversial Topics (Unless You’re Open to Debate): “Politics, religion, and other hot-button issues can be polarizing. If these topics naturally come up and you both enjoy a respectful exchange of ideas, that’s great—but avoid making the conversation feel like a debate club meeting.”
• Negative Rants (Work, Dating, Life in General): “Complaining about work, bad dates, or life frustrations can kill the vibe. Instead of venting about how awful modern dating is, shift the focus to what you’re excited about or looking forward to.

“The goal of initial interactions aren’t to have deep, heavy discussions, but rather to get a sense of fundamental compatibility in a way that feels natural and engaging,” she adds. “You want to cover topics that reveal values, lifestyle, and long-term outlook—without making it feel like an interrogation.”

Phase 1: The first 10 minutes

Now that we’ve covered what not to talk about, we can cover what to ask in one of the most important moments of the date–when you first sit down. These first date questions are key primers, the ones to ask after you’ve said hello, and settled in somewhere comfortable. Sure, they’re kind of snoozy, but they’ll set the tone for your date, and give you immediate things to talk about: “Oh, you went to Notre Dame? So did my cousin!”

1. What do you do, and how long have you been doing it?

2. Where are you originally from?

3. Where did you go to school?

4. What was your major?

5. Where exactly do you live in [insert your city or town here]?

Phase 2: After the first drink arrives

Now that you’ve gotten the primers out of the way, it’s time to get a tad more specific. Questions over the first drink should be an equal mix of inquisitive and casual, and should allow you to start gauging their true personality. What are their likes and dislikes, what do you have in common, what does he or she do in their spare time?

“Getting to know someone isn’t just about asking questions—it’s about asking the right ones that spark curiosity, storytelling, and real connection,” Bendory says. “The best questions aren’t just about gathering facts; they invite your match to share who they are, not just what they do.” These questions below will allow you to break the ice while still getting insight into your date’s hobbies and interests.

6. What’s your ideal way to spend a Sunday?

7. Are you more of a TV person, or do you prefer movies?

8. Depending on the above answer, ask what they’re watching, or what they’ve seen lately.

9. What type of music are you into?

10. What’s the best trip you’ve ever taken, or one you’re dying to take?

11. Have you read any good books recently?

Phase 3: Things are starting to get comfortable…

If you and your date are really starting to hit it off, it’s time to start slipping in some slightly more personal questions, while making sure neither of you feel compelled to reveal too much. Some of these questions may seem silly at first, but they can be very telling. They’ll also further loosen the two of you up and can lead to some funny, entertaining conversation.

The key is to ask a variety of questions. Not only does touching on a lot of different topics keep the conversation interesting, but it helps reveal genuine compatibility. “A mix of lighthearted and thought-provoking questions makes the interaction memorable and enjoyable,” Bendory adds. “Some people need the right question to open up. When you ask diverse questions, you give your match a chance to share different sides of themselves.”

12. Are you a cat person or a dog person?

13. If you could only eat one thing for the rest of your life, what would it be?

14. Do you have any nicknames?

15. If you won the lottery tomorrow, what’s the first thing you’d buy?

16. Do you have any siblings?

17. If you could be any person for a day, who would it be?

18. What’s your biggest pet peeve?

19. Coffee or tea?

20. Where else would you consider living?

21. Are you as tired of Taylor Swift and Travis Kelce (or another celebrity couple) as I am?

22. Do your parents still live in the house you grew up in?

23. What’s one thing on your bucket list that you’re determined to make happen?

24. Are you a morning person or a night person?

25. Do you ever cook?

26. Do you like your job? What do you want to do next?

27. What kind of friendships do you value most?

28. Do you consider yourself career-driven?

29. What are you most passionate about?

30. When’s your birthday?

Phase 4: Sign Me Up for a Second Date 

Time to seal the deal—the last few minutes of a date are crucial to make sure a second date happen. If you think things went well, don’t be afraid to let him or her know. The final questions should easily transition you out of the date while subtly implying that you’d be down to meet up again.

31. Can I split the check with you? Okay, can I at least leave the tip?

32. How is work looking for you this week?

33. Did you like this place?

34. Do you have any fun plans for the rest of the weekend?

35. Do you have a busy week coming up?

36. How are you getting home?

Phase 5: Let’s Keep the Date Going

This phase is tricky, and should only be reserved if you’re really feeling strong vibes. If you’re confident, ask if she or he would like to continue the date someplace else. Suggest a (PG-rated!) alternate ending to the night rather than simply going your separate ways after drinks or dinner.

37. There’s this cool bar I know around here. Want to go grab a drink?

38. Want to get coffee/dessert after this somewhere else?

39. My friend’s actually having a party a few blocks away, do you wanna stop by?

40. What are we doing after this?

A version of this article was originally published in 2016.