How To Have A First Date That Doesn't Feel Like a Job Interview

Andrew Zaeh

So you're meeting an internet stranger in a bar and, naturally, you want to gauge right away if they could be a serial killer. Maybe the dude in question posted only one Tinder picture wherein his eyes were visible, and that single shot betrayed a sort of emotional dead zone; maybe the woman you've been chatting with keeps bringing the conversation back to unsolved murders and the different kinds of knots she can tie (sounds like a keeper, tbh). Maybe you want to just very quickly pin down whether or not this stranger is danger, so you hit them with a bunch of rapid-fire questions to establish a context, a background, a few opportunities to fact-check the information they've previously divulged over text. But before you know it, the first date starts feeling like an interview, or a quiz, and your date seems miffed.

Your desire to avoid stranger danger is not misplaced, but many people aren't going to like or appreciate the feeling of being interrogated — especially by someone they've just met. It can feel invasive, stressful, and wholly antithetical to the natural flow of a first conversation, but so many of us do it when we're excited or nervous. If you're looking for love or even just sex, though, you don't want to drive away prime candidates.

"One of the most common complaints I get after a first date is that it felt like a job interview," Lori Salkin, SawYouatSinai Senior Matchmaker and Dating Coach, tells Bustle. "Question after question, almost a total interrogation. Leaving no room for chemistry or romance."

None of us wants to make the first impression of having not even a modicum of chill, and probably each of us would prefer not to feel backed into a corner when we still have three quarters of our beer to finish. So here's how experts say you can make a first date feel less like a quiz.

1Leave Your List Of Questions At Home

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Maybe you are going into the date with a certain number of things you want to know, possibly a catalogue of dealbreakers you'd like to check immediately because you're busy and need to stick to the agenda. Resist the impulse to check boxes.

"Don’t come in with a script, a list of questions to ask or answer," Salkin says. "If you have a script that you are planning to get through you’re not leaving yourself open to pick up on emotion and create a connection or give off emotion and vulnerability. It is the stories and tangent conversations between questions that truly enable individuals to build connections with one another."

In other words, let your date take the time to respond to a question you ask, and listen to their answer. Take that as a jumping off point for your next comment.

2Keep Your Questions From Getting Too Personal

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"You may be aching to ask how many people your date has slept with — but don’t. Not on the first date," New York–based relationship and etiquette expert of Relationship Advice Forum, April Masini, tells Bustle. "You may want to know how much money they make — but don’t ask on a first date. And you may want to know what kind of debt your partner has, but don’t come right out and ask this on a first date."

Sure, there are pieces of information you might find critical to assessing a person's long-term potential, but this is a first meeting and not a marriage test. No one wants to talk credit scores instead of what should be casual banter. "There are certain questions that can turn a nice first date into the definition of awkward," Masini says, "because they’re inappropriate for someone you’re just getting to know."

3Treat Your Date As You Would A New Friend

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In determining what questions are too probing, it may help to take yourself out of a romantic headspace. "It is not as an aggressive job interview," Salkin says. "You don’t have this one hour to decide if this person can be your soulmate. If you focus on getting to know your date slowly and in an easygoing manner and focus on building the foundation of a friendship (with flirting of course) you will give off a much better impression of yourself and gain a much better understanding of who your date is."

If life-long companionship is in fact what you're after, you might be particularly well-served by Salkin's approach. "Finding a spouse is first finding your best friend and you would not make a best friend solely by quizzing them to see if they check off your list," she says. "Get to know the person fully and don’t worry so much about checking off a set of boxes." And don't worry so much about long-term legal commitments on date one — one step at a time.

4Talk About Topics At Hand

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With an eye to keeping your date from feeling like you brought in a formulaic questionnaire, base your conversation on the activities at hand. Rather than dredging up exes or kids or taxes or the typical questions about college, "talk about the restaurant you’re in or the food on the menu," Masini suggests, perhaps the most straightforward and easily accomplished tip of them all. You are, after all, wedged together in this shared experience for a little while, what more natural conversation topic is there?

"Talk about the movie you just saw or neighborhood you’re strolling through together," she says. "Keep the conversation about the present, and let it flow. This will keep your partner from feeling grilled and you from feeling like you’re running someone through their paces."

5Don't Monopolize The Conversation

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"If you just ask question after question or just answer question after question it will very quickly be a one-sided conversation," Salkin says. Ask one question, and allow your date time to flesh out a response — and get in a few of their own questions, too.

It feels decidedly weird to sit there while someone runs through all the things they'd like to know about you, a possible new squeeze. And that feeling of awkwardness, pressure, one-sided interest has a tendency to tank whatever prospect there was of going out again. After all, you may leave the date knowing everything you wanted to know about the person sitting across from you, but they may leave without any concrete info about you — other than that you're perhaps a little nosy.

6Compliment Your Date

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"This is one of the most charming things you can do on a first date, and it’s part of the art of flirtation," says Masini. Are you impressed by her encyclopedic knowledge of deep sea creatures? Is he sporting a particularly fetching facial hair arrangement? Are they an unassuming bar trivia star and are you floored? Say so!

Complimenting your date, whether it's about their style or their accomplishments, is a good way to prevent your date from feeling 'grilled' by rapid-fire questions, Masini says. "[A compliment] can be charmingly disarming and sets the tone for a much more romantic and open conversation than you might otherwise have had," she says.

7Treat Your Date As You Would Want To Be Treated

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Treat your date as you would want to be treated; pause before you fire off a question and consider how you would react if the tables were turned. Would you feel as though your mental space were being invaded by inquiries into your student loans or your sexual history 20 minutes after just meeting someone? If you can see where requesting a particular piece of personal information might rankle a relative stranger, keep your question to yourself.

If the date goes well, you stand a much better chance of eventually learning everything you wanted to know about this person — gradually, over time, and not in the course of one meal.