5 Questions to Ask on a First Date (& 2 to Avoid), According to a Matchmaker

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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, we turned to Susan Trombetti, relationship expert and owner of Exclusive Matchmaking in Washington, D.C. “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 tells us. 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, five questions to ask on a first date and two to avoid.

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5 Great First-Date Questions

1. Who was your first crush? What were they like?

Trombetti tells us 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, we promise).

2. Who was your first kiss? Where was the most romantic place you ever kissed someone?

“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.

3. Tell me two truths and a lie.

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.”

4. What would you do with your life if money didn't matter?

A person can dream. “This is always an interesting answer and can be revealing,” Trombetti tells us. “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.

5. Where's your favorite place in the world that you’ve traveled, or a place you’re dying to visit?

The point of this question isn’t necessarily to add to your travel bucket list through secondhand wanderlust. Trombetti tells us 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.

2 First-Date Questions to Avoid

1. Anything too specific about their job

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.   

2. Anything about their ex

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?

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sarah stiefvater

Wellness Director

Sarah Stiefvater is PureWow's Wellness Director. She's been at PureWow for ten years, and in that time has written and edited stories across all categories, but currently focuses...