Tips For Great First Date Conversation

First-date conversations are tricky. The difference between dull, boring small talk and asking overly personal questions can be difficult to see in the moment. Often, singles opt for the safe bet and spend their dates talking about their jobs. Discussing what you do for work isn’t a bad place to start, but can we do better? Yes!

Don’t waste a great opportunity to genuinely connect with your date. This is the time to get to know them, not just learn about their job. Asking interesting questions can help keep the connection going and reveal the shining personality of your new love interest. Read on for our advice for having great conversations and some fun thought-provoking questions to get you started.

Start With “How Was Your Day?”

Dating and relationship coach and author of The Secret Rules of Flirting, Fran Greene recommends starting off simply. By asking your date how their day went, you can show them right away that you’re interested in hearing their perspective. It can also help your date get more comfortable talking to you. “It sets the stage for your date to start talking about something they know,” she says. From this point, they can share as much or as little as they’d like.

Stay Positive

It’s true that your mindset matters. The way you think about things can profoundly affect your behavior. That means that believing your date will go poorly makes you more likely to behave in a way that makes your date go poorly. You can avoid this self-fulfilling prophecy by being conscious of your negative thoughts and trying to reframe them in a more positive light. For instance, you might find yourself worrying that your date won’t like your outfit, your hair, or your jokes. You can try to change your mindset by reminding yourself that you look and feel great in your outfit. 

You are funny, smart, and charming, but your date won’t see that if you allow negative thoughts to control your behavior.

Practice Active Listening

Active listening means being fully present, giving your date your undivided attention, and genuinely hearing what they have to say. When your date speaks, pay attention to their words, the emotions behind them, and their body language. Get rid of distractions and make eye contact to show that you’re interested in the conversation. Active listening sends a powerful message to your date that they are valued, and what they have to say matters to you.

12 First Date Questions

The key to great first-date conversation is giving your date opportunities to talk about things they enjoy. These questions will keep the conversation positive and allow both of you to show off your best selves.

1. Do you have any passion projects that you’re excited about right now?

Learning about someone’s passion projects can give you a sense of their drive and what they find fulfilling outside of their job and regular responsibilities. Asking the question in this way also invites them to share something they are enthusiastic about, hopefully sparking an interesting conversation about your date’s passions.

2. What is something you’ve always wanted to do but were afraid to?

This question invites your date to share something personal and potentially vulnerable. It shows that you are interested in getting to know them on a deeper level. Discussing your fears and aspirations in a lighthearted way can lead to a more genuine and meaningful conversation.

3. If you learned a giant meteor was going to hit the Earth in 48 hours, how would you spend your time?

This is a silly question that will encourage your date to reflect on their values and priorities. Their choices and the reasons behind them could give you a fuller understanding of who they are. Depending on the answer, it may help you understand if your values are aligned. If their priorities align with yours, it could be a positive sign of compatibility.

4. If you could switch lives with someone for a day, who would it be?

This is a fun and lighthearted way to find out more about your date’s values and interests. By inviting your date to share details about someone they admire or find interesting, you can learn more about what they’re paying attention to regularly. For example, if they name a political figure, you can infer that political action is important to them. 

5. What is one thing you know now that you wish you had learned at 18?

We all find things out the hard way sometimes, and your date is bound to have a story or two about lessons learned. This allows your date to tell an anecdote from their past and to show off some of the ways they’ve grown. This honesty creates a sense of openness and authenticity, fostering a stronger connection between you.

6. What’s the most fun thing you’ve done recently?

Asking this will give you some insight into what your date likes to do for fun. They might tell you about a recent beach vacation, a sunrise hike, reorganizing their pantry, or something entirely unexpected. You may be able to discern how adventurous or spontaneous they are. Their answer could also give you insight into whether they’re a social butterfly or a more quiet type, what kind of activities they enjoy, and so much more.

7. What’s your favorite meal?

Food is a universal topic. Asking about your date’s favorite meal can serve as a great conversation starter and a way to bond over shared culinary experiences. Their answer may also tell you more about their background. They might love an old family recipe, or maybe they’re still in love with a dish they tried on a trip abroad.

8. What is something that people are always surprised to learn about you?

People often have hidden talents, unexpected quirks in their personalities, or unique life experiences. This question allows your date to talk about something they might not think to bring up otherwise, letting you see another facet of their unique personality.

9. What was your dream job when you were a kid?

While this question is likely to segue into a conversation about careers, it introduces the topic in a fun and light-hearted way. Kids’ career aspirations typically range from unrealistic to outlandish. Superhero, Movie star, and Professional Athlete are all popular answers. Whether this sparks a deeper conversation or just a good laugh, it’ll be a fun chat.

10. What’s the best piece of advice you’ve ever received?

Talking about personal advice can help build a sense of connection with your date. It creates a shared space for vulnerability and understanding without crossing boundaries. Your date might tell you about someone they love who helped them, giving insight into their life. This question can help you have a more intimate and meaningful conversation without veering too far into heavy subjects.

11. What’s your favorite way to unwind after a long day?

How someone chooses to relax says a lot about their interests, hobbies, and social habits. You could discover they like to unwind by going for a relaxing three-mile run, or they could reveal that the time they spend with loved ones is the most relaxing part of their day. 

12. Who is the person you talk to the most? 

This question can tell you about the important relationships in your date’s life. Do they talk to their best friend most? The way someone talks about their friends can be very revealing of their character, so pay attention. You might also learn that their #1 conversation partner is their boss, their mom, or their cat. 

When in Doubt, Be Yourself

Knowing what to ask on a first date can be difficult sometimes but don’t get too hung up on doing things “right”. Be yourself and keep your intentions well-meaning. The art of asking good questions is about having a genuine curiosity to want to know someone on a deeper level, not about getting the scoop on their past or sniffing around for red flags. Unconventional questions will help you see a less rehearsed side of your date, which will help gauge if a real connection is possible.