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10 first date questions to ask to avoid awkward small talk, according to relationship experts

Ask these questions to avoid feeling anxious.

first date, first date questions, first date conversation, first date advice, first date tips

First date questions relationship experts and therapists recommend asking.

First dates are the first step to pursuing a new romantic relationship. But anyone who's ever been on one knows that they can also create a lot of anxiety.

"First dates can feel awkward because nerves naturally make us want to protect ourselves," Danielle Sethi, a licensed marriage and family therapist in Florida, tells Upworthy.

But asking engaging first date questions can help you avoid awkward small talk or feeling anxious, and allow a true connection to start growing. "Once one person shares something a little vulnerable, it signals it’s safe for the other person to do the same and go a little bit deeper," adds Sethi. "Ideally then the conversation starts to feel balanced, meaningful, and engaging."

Here are 10 awesome, expert-approved first date questions to come prepared with:

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"What’s a passion or hobby that makes you lose track of time?"

"This shows you how someone taps into presence, play, and their natural energy," Lauren Salaun, a relationship expert and host of the AMPLIFY podcast, tells Upworthy. "It gives you an idea of what fascinates them and brings them joy."

"What do you do that brings you joy?"

"This question helps someone talk about their interests in a way that isn’t tied to productivity or work," Saba Harouni Lurie, owner and founder of Take Root Therapy, tells Upworthy. "It invites someone to talk about what matters to them beyond how they make a living."

"When do you feel most like yourself?"

"This question gently explores identity and authenticity," Brie Temple, Tawkify's CCO and chief matchmaker, tells Upworthy. "It encourages the person you’re asking to reflect on their most true moments, whether that’s being with close friends, creating something, helping others, etc. It’s a light way to build emotional trust and vulnerability."

"What is one thing you’re currently learning, or unlearning, about yourself or the world right now?"

This question bypasses the typical job description and hobbies list.

"It immediately requires a level of self-reflection that signals emotional maturity and an openness to growth," Claudia Giolitti-Wright, founder and clinical director of Psychotherapy for Young Women, tells Upworthy. "Asking what they are unlearning is especially powerful because it acknowledges that everyone is a work in progress and allows the person to share a recent shift in perspective, which is inherently intimate and connection building."

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"Who is your role model?"

You can learn so much about your date's values and close relationships by asking this question.

"It can also reveal healthy attachment relationships in their life (people they look up to and trust) which is linked to a more secure attachment style," Sethi says. "Partners who've had secure attachment figures in their life are often better able to navigate future challenges and conflict, making this question helpful early on. Of course we can't draw conclusions, but we can start to notice patterns in their ability to connect strongly and securely with others while being themselves."

"Where are you from, and how does that inform who you are today?"

"This question opens a window into someone’s story. Getting someone to talk about where they’re from invites reflection on upbringing, culture, and identity," Harouni Lurie says. "It's a natural way to get to know someone on a deeper level."

"If you had an hour of completely free, unstructured time today, what would you spontaneously decide to do with it?"

"Many people, especially on first dates, describe 'fun' as activities that sound impressive or are socially desirable. This question is designed to reveal how a person naturally recharges and what restorative activities they genuinely value when they don't have to put on a show," Giolitti-Wright says. "The answer tells you a lot about their inner world, their relationship with solitude or connection, and whether their definition of fun aligns with yours in a way that truly brings comfort."

"If you could pick three cuisines to eat for the rest of your life, what would they be?"

"This question is light and playful, and always brings laughter and levity!" shares Harouni Lurie. "Food is universal, making this question perfect for easing tension and sparking easy rapport. It's a perfect ice breaker."

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"What’s the most beautiful or chaotic thing you’ve seen happen in a public space recently?"

"This question is a fantastic way to assess a person’s perspective and values without asking heavy questions," explains Giolitti-Wright. "If they talk about the chaotic thing, you learn what frustrates them or how they handle stress. If they talk about the beautiful thing, you learn what brings them joy and what details they notice in the world. This exercise in shared observation shifts the focus away from the self and onto the external world, building connection through a shared, interesting narrative."

"Have you had a long term relationship?"

Find out more about your date's dating history with this question.

"Understand whether you are matching up with someone who has had established relationships or scars from the past," says Sethi. "You may also ask whether they have ever been to therapy with a partner to assess their openness to learning and growth."