12 first-date questions that actually work

Most first dates go wrong in the same quiet way: two nice people trade job titles, home towns and the names of their siblings, and go home feeling like they've filled in a form together. The fix isn't being more interesting. It's asking better questions.

Good first-date questions have three things in common. They're easy to answer, they can't be answered with one word, and the answer tells you something about how the person thinks, not just what they've done.

There's research behind the idea, too. In a well-known 1997 study, psychologist Arthur Aron and colleagues had pairs of strangers take turns asking each other a set of questions that slowly became more personal. The pairs who did ended up feeling noticeably closer than pairs who made small talk for the same length of time (Aron et al., 1997). The trick is the gradual build. Don't open with "what's your biggest regret?"

Warm-ups (the first drink)

1."What was the best part of your week?"

Better than "how was your week?", which gets you "good, busy." It also tells you what makes them happy.

2."What are you weirdly good at?"

Everyone has one: parallel parking, remembering birthdays, assembling flat-pack furniture without the instructions. People light up talking about it.

3."What did you want to be when you were small?"

A gentle way into their story, and it's usually funny. Follow up with "how close did you get?"

4."What's the last thing you got really into?"

A show, a hobby, a rabbit hole at 2 a.m. You learn what holds their attention.

Getting into it (the second drink)

5."What does a perfect Sunday look like for you?"

Quietly one of the most useful questions in dating. You find out whether your ideal Sundays could ever overlap.

6."Who in your life do you talk to most?"

Friends, a sibling, a parent, nobody? You learn who matters to them and how they keep people close.

7."What's something you've changed your mind about?"

Listen for how they talk about it. Someone who can say "I was wrong" on a first date is a green flag.

8."What are you looking forward to?"

People with a life they like have an answer. It also opens the door to plans, and plans are how second dates happen.

If it's going well (dessert)

9."What made you swipe on me / say yes to this?"

Flirty, a little brave, and you'll learn what they noticed.

10."What's your idea of a great date, if money and time didn't matter?"

Fun to answer and a free tip for date two.

11."What's a small thing someone did that made you feel really cared for?"

The closest you'll get to "what's your love language?" without sounding like a quiz.

12."So, should we do this again?"

Yes, that's a question. Asked with a smile at the end of a good night, it saves both of you three days of wondering.

Both fears have the same answer: follow up. Ask the question, then ask about the answer. "Wait, you did what?" beats moving to question six every time.