- First date conversations can get tedious and predictable.
- Famed sex and relationships therapist Esther Perel shared how to ask better questions.
After a bout of dating app fatigue, you redownload Hinge and revamp your profile. You get one match, two, five. Your first conversations are easy, and you set up a few bar dates.
Nothing is necessarily wrong, but when your date starts talking about their software engineering job, your eyes drift over to the gilded wallpaper behind them. When you exchange quick tidbits about your home states and college majors, your leg starts to twitch from the monotony of the same script you followed two nights ago. When they ask about your weekend plans, you want to guzzle your negroni and sprint into the night with a witch’s cackle, because at least you’d feel alive.
Rest assured: If you’re bored on first dates, it’s because they’re inherently boring. But luckily, the fix is easier than you think.
Esther Perel, a famed sex and relationships therapist and podcast host, told Business Insider that common first date questions like “What do you do?” and “Do you like your job?” are recipes for tedium.
“These kinds of dead-end questions resemble job interviews quite often,” she said.
Perel, who recently released a new edition of her card game that features thought-provoking questions to ask the people in your life, said that many first date questions veer into data collection.
“A date that gathers data is deadly,” Perel said. “A date that evokes curiosity, discovery, serendipity, happenstance — that becomes interesting. That's the one that goes on for four hours and you didn't see the time pass.”
Perel shared her tips for making a first date actually fun. Because even if nothing else comes of it, at least you won’t be half asleep.
1. Ask questions that invite stories
Perel believes the best first date questions prompt the other person to tell a story — especially if it’s one they didn’t expect to tell.
For example, she said “How long have you lived in New York?” is boring because it ends with you saying the length of time you’ve been in a city.
A different twist on the same question could be “If cities were people, which one would be your best friend, which one would be your lover, and which one would be your long-term relationship?”
“And then people start to tell you the story of their connection to New York and they tell you the story of their connection to Rio or Berlin or Amsterdam or Madrid,” she said.
Similarly, if you’ve already broached the topic of therapy, you can spice things up by asking them what they would lie about to their therapist.
“The assumption is that you shouldn't or you don't, but in fact, probably many of us do,” Perel said. “And so it opens up a kind of door behind the door.”
2. Be on the move
Meeting up at a bar, cafe, or restaurant can feel easy and low-stakes, but Perel generally advises against it for first dates. “Don't sit in front of each other or in a noisy bar,” she said. “Go for a walk, go biking, go dancing — but be in movement.”
She said when you’re sitting across from each other, it adds a formal, stiff energy to the interaction because if you look away, it looks like you’re disinterested.
But when you stroll through a park, you can switch back and forth from glancing at each other to gazing around you.
“You have 10 different stimuli in front of you to talk about — the water, the sky, the motorcycle that just passed,” she said. “And then you are freed from the interview.”
If you feel comfortable committing to a bigger date, she also recommended attending an event that you can talk about after. Perel said she’s had some people tell her they’re taking new-ish partners to her US speaking tour, as a way to easily break the ice after.
3. If you get nervous, bring pre-written questions
If you desperately want to venture outside “what did you get up to this weekend?” but feel intimidated by deviating from the expected first date questions, Perel recommended prepping a few pre-written ones.
She said you can open with something like “I’ve done this for a while, so I’ve been thinking about how this can be more fun, more interesting.” That way, you can set up the expectation that the questions might be a little more unusual than what they’re used to.
To make it even easier, she said you can take a few cards from her game or another Q&A deck and ask them to pick one. “You make it low-stakes, low-investment, but potentially high return,” Perel said.
4. Don’t fixate on your best side
While Perel said apps can be great at expanding your access to new people, the downside is you can get into the habit of pre-packaging your shiniest qualities.
“We are not products, and we don't need to sell ourselves,” she said, adding that what’s compelling isn’t focusing on what we think makes us fascinating or impressive, but by eliciting curiosity in the other person.
One way to do that is to ask and answer questions that don’t make you out to be perfect. “People shouldn't just tell a story in which they were the saint and the other one was the wrong one,” Perel said.
Instead of waxing poetic about your workout routine, share the rule you love to break or your most tenacious vice, she said.
5. Open up without dumping everything out
While dates that tread surface-level waters are dull, Perel said the alternative isn’t to dive headfirst into trauma-dumping territory.
Perel said the way you open up should make sense in the context of the date and your relationship to the person, instead of “here's my wallet and I'm taking out all the stories of my life.”
Even if a question feels personal, you can take a beat and go much lighter if your full answer feels like an overshare. “You do not necessarily need to elicit empathy and compassion for the woundedness inside of you on date number one,” she said. “Because you're more than that, too.”
It’s another reason why she loves dates that leave the bar, because there’s always something else that can grab your attention and take conversations in new directions.
From the questions you ask to the activity you do, a date should be “a story that unfolds,” Perel said. “It's not a therapy session.”