13 Unique and Fun First Date Questions to Ask a Guy

couple outside in each others arms

First dates can be thrilling, nerve-wracking, and everything in between. But what are the best questions to ask a guy on a first date?

There’s no right conversation for a first date, but a good rule of thumb is to aim for a lot of fun and a little intimacy.

We’ve broken our first date questions into two sections so that you can tailor your choices to what suits you.

Basic Questions to Ask a Guy

1. Open with a question about his profile

One of the perks of online dating is that you already know a little about your date before you even meet them.

This makes starting a conversation easy. Take your cue from his profile and begin by asking him about something he’s posted.

Whether it’s his really exciting job, his cute dog or the beautiful hike he just went on, asking him about a specific detail shows that you’re paying attention and are genuinely interested in his life.

2. What are you most excited about this season?

From summer kayaking to cozy Christmas markets in the snow, seasonal activities are an easy way to talk about the near future.

Discovering what he’s excited about allows you two to get to know each other while also subtly introducing some fun ideas for a second date.

3. Why did you choose your career path?

Talking about your careers is a tried and tested first date topic, so don’t be afraid to throw it into your first date conversation.

Asking him why he chose that path gives insight into his values and passions, and might even spark a conversation about his life growing up.

4. What skill are you most proud of?

Depending on the tone of your conversation, this can be either a playful question or spark a serious discussion.

Whether he’s a pro at parallel parking or neurosurgery, this question will reveal the little things that often take several dates to discover.

5. What movie can you watch over and over again? 

Talking about your favorite books and movies always gets the conversation flowing.

If you’ve got the same picks it creates an instant bond, and if his faves are things you’ve never heard of before then it’s a great opportunity to learn about something new.

6. Describe what you love about your best friend

This is a deep question masquerading as a playful one. The qualities that we love about our friends are often the ones we value in a romantic partner.

Kindness, loyalty, a sense of humor, these essential qualities open the door to a relationship where your partner is both a lover and a friend.

7. If you could have a dinner party with any five people (fictional, historical, etc.) who would they be?

This question is a total classic. It’ll keep the conversation flowing smoothly and show you what kind of people he admires.

Meaningful Questions to Ask a Guy

8. What drew you to my profile?

This number is a fun, flirty segue to a more serious conversation.

Chances are he thought you had a stellar dating profile, so asking him about what caught his eye is both intimate and engaging.

It’s also an opportunity for him to talk about the qualities he values in a partner and it’s a bonus because he must have seen these qualities in your profile.

9. What are you looking for in a relationship?

While this might feel like you’re coming on a little strong, discussing realistic relationship expectations is one of the most important things you can do on a first date.

This doesn’t have to be a promise of a relationship together, but knowing what he wants can help you decide whether a second date will be worth your while.

10. Where do you see yourself in 5 years?

This question doesn’t just apply to relationships, it’s also a discussion about physical space. Maybe he sees himself as the head of his company, or maybe he sees his job taking him across the world.

This is your chance to find out if he’s ambitious, what his goals are, and whether they align with your own.

11. Which person in your life shaped you the most?

Having an open and supportive discussion about childhood deepens your connection with someone. It encourages intimacy and trust.

Talking about his role models gives you an insight into the kind of parent he might be, what qualities he thinks are important, and what lessons he would like to pass on to a child.

12. If you were elected President, what would be your first three decisions?

Forget about politics as a taboo date topic, studies show that most people would be happy to discuss their political opinions on a first date.

If political leanings are important to you when choosing a partner, talking about politics early on can be essential in deciding whether your date is a serious contender for a long term relationship.

13. Describe your perfect Sunday

Sunday is usually a day of relaxation and laughter. How people choose to spend their Sundays says a lot about them. Maybe he likes to spend it outdoors or curled up with a good book?

If your Sunday plans align then it’s a pretty good sign that you’ll enjoy spending downtime together, and that’s important.

A couple who’s happy doing nothing together is a happy couple indeed.  

If you’ve had a fun date together, there’s a genuine connection, and you can see a future that aligns, then ask your crush out on date number two! Who said guys had to make the first move? 

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