7 Unexpected But Useful Questions To Always Ask On A First Date

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Knowing what to talk about on a first date can be nerve-wracking. Ideally, you both click and the conversation flows easily, but sometimes you have to have more of a plan of attack — and asking the right questions can make all the difference.

"Don’t try to impress your date with [wild] stories and facts about yourself; this will almost always backfire," online dating consultant Stacy Karyn tells Bustle. "You should rather learn how to engage, listen, and genuinely respond to your date. This will make them feel valued and excited to see you again."

But what kind of questions can you ask? Well, even on a first date you may be able to go deeper than you would think. Don't shy away from personal or unusual questions, because those should actually be exactly what you're asking. "Asking questions that are more personal will not only get you the answers you need but will also make your date different than most dates [they've] been on," Anna Morgenstern, a dating and relationship coach in NYC, tells Bustle. "[They'll] feel more connected to you because you asked questions to really get to know [them], rather than just getting [their] stats. You'll build a connection much quicker if you come prepared with questions that are important to you."

So here are some unexpected questions you should try on your first date — because it's best to get some things out on the open, right from the get-go.


"How's Your Relationship With Your Parents?"

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Zen psychotherapist and neuromarketing strategist Michele Paiva tells Bustle that asking "What is your relationship like with your parents?" is a great way not only to get some background on the person, but also to see how they handle adversity. Even though asking about your childhood might seem really deep on a first date — it's also really revealing.


"How Would Your Friends Describe You?"

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Sometimes, asking about someone else's viewpoint is really telling, even if we rarely think to do so. “Asking them what their friends say about them provides them the safety of describing themselves from another person’s point of view,” relationship expert, Dr. Karin Anderson Abrell, tells Bustle. “In addition, you get to learn about their friendships, which of course, ultimately says a lot about who they are.” Win-win.


"What Are You Looking For?"

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Another question that gets right down to the point. Jump in on the first date by asking about where they're at right now. "While it might seem taboo, you do want to ask the question, 'What are you looking for in a relationship?'" BetterHelp telehealth counselor and psychologist Nikki Martinez tells Bustle. "While some might argue this is early, I would argue that this lets you know what page each of you are on, and if they are likely going to be headed in a similar direction, at a pace you can live with." You might as well get right down to it.


"What's The Best Vacation You've Ever Been On?"

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Another weird but telling question, asking about their best vacation can be really revealing. “The answer to this question will give you an idea of your date’s sense of adventure and what they consider great or standard,” Patt says.


"What Is Your Greatest Achievement?"

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Another great first date question? One that helps you learn more about them, both by the content of their answer and the way they answer it. "What is your greatest achievement?" Salama Marine, psychologist, tells Bustle. "This is a good opening personal question to discover something about the person you’re seeing without them being able to show off too much."


What Are Your Thoughts On Monogamy

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One way to jump right in? Ask your date how they feel about monogamy or if they've ever been in an open relationship. "The question of monogamy is no longer a given," author and relationship expert Susan Winter tells Bustle. "You want to make sure you're on the same page while constructing your partnership foundation."

Not only can you make sure you're on the same page with this question, whatever that page may be, you can also open up a dialogue about relationships and commitments more generally.


"If You Could Have Any Superpower, What Would It Be?"

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This is a silly question, but it's a lot of fun, too. "You can tell so much from the answer, or lack thereof," Crystal Rice, licensed therapist at Insieme Consulting, tells Bustle. "Do they really give the question the time of day and think through an answer? Is their answer focused on helping others? Is their power selfish in nature? Are they creative with their response, or do they go for the 'normal' stuff and then move on?" Just know they'll probably ask the question right back.

A first-date conversation doesn't have to be stilted or overly formal. Don't be afraid to ask the deep questions right from the very beginning. It will save you time and make the date way more interesting.