09.19.2019

13 Unique and Fun First Date Questions to Ask a Guy

Starting a new relationship can be thrilling, nerve-wracking, and everything in between. The first few dates are a delicate balance, trying to dig deep and form a genuine connection without coming on too strong. So, what are the best questions to ask your crush 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 “getting to know him” and “digging deep” for 13 questions to ask a guy that helps you form a real and meaningful connection.

Getting To Know Him: Fun and Flirty 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 the conversation effortless – 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 did, 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 lets you get to know each other while giving you the opportunity to subtly introduce fun ideas for a second date.

3. Why did you choose your career path?

Talking about your careers is a tried and true first date topic, so take the opportunity to use the classic conversation starter to dig a little deeper. 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 a serious discussion. Whether he’s a pro at parallel parking or at neurosurgery, he’ll let you in on the little things that often take several dates to discover.

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

There’s nothing wrong with keeping it light and easy, and 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 it’s something you’ve never heard of it’s a great opportunity to get him talking about something he loves. 

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 can 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?

Dr. Arthur Aaron’s 36 Questions to Fall in Love asks “Given the choice of anyone in the world, whom would you want as a dinner guest?”. We’ve expanded that a little to fit the mood of a first date – offering five options lets you discover more of his personality and creates more chances to find things you have in common. 

Digging Deep: The Meaningful Questions to Ask a Guy

8. What drew you to my profile?

This is a fun, flirty segue into more serious conversations. Chances are he found your profile attractive, so introducing that idea adds a little intimacy into the conversation. It’s also an opportunity for him to talk about the qualities he values in a partner, and a bonus because these are already qualities you possess.

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?

Being on the same page about your future doesn’t just apply to relationships. It’s also a discussion of 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 the chance to find out if he’s ambitious, what his goals are, and whether they’re a match for your own. 

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

An open and supportive discussion about his childhood deepens your connection, creating intimacy and trust. Talking about his role models is also an insight into the kind of parent he might be – what qualities he thinks are important, and what lessons he would want 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 – we found that 65% of those surveyed 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

At the end of the date, the best thing you can discover is that you want to spend more time with them. Maybe it’s as simple as a second date, or maybe there’s a part of you that can imagine growing old together. When they look at their future and picture the best possible outcome, is there a partner in that picture? And is their ideal future one that you can see yourself being a part of? If you’ve had a fun date together, there’s a genuine connection, and you can see a future that aligns, chances are you won’t regret inviting them on date number two.

If you’re wondering how to get the conversation flowing, our 13 questions to ask a guy are a great way to start off the date. Discover even more tips for finding success with online dating to find that special someone today.