10 Questions to Ask on a First Date, According to a Matchmaker

Ahh, first dates. Questions about siblings and favorite drinks interspersed with awkward silences and anxiety. But as uncomfortable as it can be to meet a prospective partner for the first time, it’s unavoidable when it comes to finding your person. To make the experience as painless as possible, I turned to relationship expert Susan Trombetti for advice on questions to ask on a first date. “As a matchmaker, when it comes to first date questions, in theory, I hate them because it's not an interview but always turns into one,” she says.

But because they’re a necessary evil, she has some tips for breaking the ice. “All questions asked should be flirty in nature that allow for witty banter, fun, and nostalgia,” she suggests. “You’re aiming to bring up good feelings that penetrate the facade of who they are now and rock their emotions a bit off kilter to get a glimpse of the real person sitting across from them.” Without further ado, tips for first date questions (including a few topics to avoid).

Susan Trombetti is a relationship expert and owner of Exclusive Matchmaking in Washington, D.C. As a leading celebrity matchmaker and relationship expert, Trombetti has helped discerning singles across the country discover long-term relationships and partnerships that are both rewarding and fulfilling. 

Before I get into specific questions to ask on a first date, let's go over a couple of ground rules for your first in-person meeting.

• Be yourself. It can be tempting, especially on a first date, to present the version of yourself you think the person you're seeing will like most. And while there's nothing wrong with putting your best foot forward, avoid falling into the trap of molding yourself into exactly the person you think they're looking for.
• Avoid talking about your exes. Sure, talk for a few minutes about your third-grade crush. But in Trombetti’s eyes, talking about your ex is tied with not putting your phone away when it comes to the biggest dating mistakes. Bringing up old relationships makes it seem like you’re living in the past and not actually interested in starting fresh with a new partner. Even if it’s a wild story you think they’ll love, just don’t do it, OK?
• Don't ask about long-term plans (yet). “Even if they want the same things, let the relationship develop,” Trombetti urges. “There should be some major flirting going on during the first date instead of you laying out your future plans to someone that might not even text you back.” She strongly advises against going too intense too fast, and instead maintaining some mystery and intrigue until you get a better handle on whether you’re even a match for each other. 
• Don't get too into job talk. Yes, it’s OK to ask what they do, but try not to go too much deeper than that on a first date, Trombetti warns. “This will bring up visions of an irritating coworker and ruin the energy of your date.” Also off the table? Money talk. “I think asking how much money they earned last year is a question many people wouldn't dare dream of,” so be sure to steer clear of any salary conversation—even if you’re curious how a lower-level employee affords such extravagant vacations.   

Trombetti tells me that this question is cute but not trivial. “It brings up nostalgia from 3rd grade memories,” she says, while adding, “You’re tapping into what made them who they are.” If you can’t remember your IRL crushes, try asking about first celebrity crushes (it’s eye-opening, I promise).

“Something along this line is flirty and fun with just the right amount of serious,” Trombetti says. A query like this also lets you know what their idea of romance is, a key if you see any kind of a future together. Trobetti notes that, if you’re feeling especially flirty, you can slip in the fact that you wouldn’t mind being their next kiss.

We’ve all played this game, and that’s because it’s a fabulous conversation starter. “Even though you might think it's too contrived, it isn't once you get going,” Trombetti explains, noting that she’s heard hilarious stories during her company’s virtual matchmaking happy hours. One example? “One guy talked about practically setting a restaurant on fire when he hit the candle with his cloth napkin.”

A person can dream. “This is always an interesting answer and can be revealing,” Trombetti tells me. “You’ll find out how close they are to living their version of it, and it also can reveal how responsible or idealistic someone is around money and life.” Do they live to work or work to live? This question is a great way to examine a person’s passions and values without getting too deep.

Whether you matched on a fancy dating app like Raya or were set up by a mutual friend, there are only so many surface-level facts you can know about someone ahead of a first date, and most of those are probably pretty run-of-the-mill. Asking about a surprising fact on the first date is a way to create some vulnerability without going too too deep. The best part of this question is that your date can take it either super seriously ("People are surprised that I helped raise my niece and nephew growing up") or more jokingly ("People are surprised I've been to 15 Britney Spears concerts"); regardless, the way they choose to answer the question can give you almost as much insight into who they are as their actual answer can.

You know those internet jokes about how relationships are all fun and games until you marry into a Turkey Trot family and you're up at the crack of dawn on Thanksgiving to run a race? This question can help you get a better idea of what a person likes to do in their free time. Whether they're more of a low-key, roll-out-of-bed whenever and then get brunch type or a "I've never missed Sunday morning 7 a.m. hot yoga" type, asking how they'd spend their perfect weekend can be very telling.

The point of this question isn’t necessarily to add to your travel bucket list through secondhand wanderlust. Trombetti tells me that their reasons why can reveal a lot about them (Are they a super-scheduler or more go-with-the-flow? Are they all about relaxing or hell-bent on taking in every single sight?), and the question allows you to see them get passionate about something.

This question can be a great way to a.) suss out tk, and b.) uncover potential similarities between you and this person. Let's say, for example, you're interested in something serious in the next year but your date has plans to travel tktkt. That might be an early sign that tktktk. Or, on the flip side, if your date says they tktkt and you also tktkt, that can be an early bonding experience.

Are they jazzed at the idea that animals can experience time differently than humans? Do they think it's interesting that the first taxis in the U.S. were painted red and green, despite their now-famous yellow hue? This question gives your date the chance to geek out over a seemingly insignificant fact that for some reason or other has stuck with them. Even the silliest of facts (did you know Kate Middleton did her own makeup at her wedding to Prince William?) can provide a window into the type of person sitting across from you—and what gets them fired up.

Maybe your date is ultra-proud of their PhD dissertation that earned rave reviews from their academic advisor, or maybe they still think about the time met Emma Stone at a bar and she told them they had beautiful eyes. The compliments that stick with us most say a lot about the traits we value in ourselves. Ask your date about the words of praise they've appreciated most and get a peek into how they want to be perceived in an ideal world.

1. Who would play you in a movie about your life?
2. What's your favorite thing to cook?
3. Did you have pets growing up? What were they like?
4. If you could see any musical act live, who would it be?
5. What goals are you working toward right now?
6. What's the best book you've ever read?
7. If you could become an expert at any skill overnight, what skill would you choose?
8. What the most embarrassing thing you've ever done?
9. If you could switch lives with anyone for a day, who would it be?
10. Are you normally the friend who makes the plans or the friend who just shows up for the plans?
11. What's your love language (or love languages)?
12. If you walked into a room with everyone you've ever met, who would you look for first?
13. What was your first impression of me?
14. What's your biggest pet peeve?
15. What does your ideal weekend look like?
16. What was your biggest fear as a kid?
17. Are you a morning person or a night owl?
18. What was your first job?
19. Are you a cat person or a dog person?
20. What's your favorite holiday tradition?
21. Who's your celebrity crush?
22. What was your dream job as a kid?
23. When making a bowl of cereal, do you pour the cereal or the milk first?
24. Are you an introvert or an extrovert?
25. What's the cheesiest pickup line you've ever used (or heard another person use)?
26. What's your go-to karaoke song?
27. Do you prefer texting or talking on the phone?
28. What's your guilty pleasure TV show?
29. What's the hardest you've ever laughed?
30. What's the wildest thing on your bucket list?