16 Questions To Ask On A First Date, According To Marriage Therapists

If you’re an introvert ― or just hate small talk ― few things are more stress-inducing than a first date. Keeping conversation flowing freely is no easy feat.

To help you figure out what to talk about ahead of time, we asked therapists and psychologists who work with couples to share their favorite first date discussion points. See what they had to say below.

1. What was the last thing you bragged about to your mom?

“Figure out some way to ask what makes your date proudest. You get to see your date light up and see them at their best. Common values are more important to a relationship than common interests and by asking this question, you get to find out what they really value in their life.” ― Isiah McKimmie, a couples therapist and sexologist in Melbourne, Australia

2. If you could get advice from anyone living or dead, who would you want advice from and what would you ask?

“You would be able to tell quite a lot from this question. For example, you’d be able to see how well they think on their feet, how playful or imaginative they are and you’d get a flavor for how worldly they are. Perhaps most obviously, you’d see who they admire, which would tell you if his or her values line up with yours. If they pick a political figure, it could tell you about how conservative or liberal they are. And asking what advice you’d be seeking tells you a lot about their goals in life.” ― Susan Pease Gadoua, a couples therapist and the co-author of The New I Do, Reshaping Marriage for Skeptics, Realists and Rebel

3. Do you make your bed in the morning?

“The answer to this question can reveal how much importance they place on order and tidiness versus saving time. It also allows for some interesting sharing about if they are a morning or night person and their usual morning routine.”  ― Danielle Kepler, a couples therapist in Chicago

4. What’s the worst first date you’ve ever been on?

“Only ask this question if you sense that things are going well, as their answer will reveal whether they can let their guard down and tell an entertaining story. Plus, it’s a great way to build an instant ‘us vs. them’ bond, as it requires the person to subconsciously reflect on how well your date is going compared to the one they’re recounting.” ― Spencer Scott, a psychologist in Santa Monica, California 

5. If you could wave a magic wand right now and have your life be perfect, what would that new life look like?

“This is a version of the question therapists often employ with their clients to help them think differently about a problem or issue. But it’s also useful in finding out a lot about a person’s hopes and dreams. If you’re a plugged-in city girl and your date’s answer is, ‘I’d be living on a remote mountaintop with no cell service,’ your life goals are probably not compatible.” ― Abby Rodman, a psychotherapist and the author of Should You Marry Him?: A No-Nonsense, Therapist-Tested Guide to Not Screwing Up the Biggest Decision of Your Life

6. What could you spend all day talking about?

“Even a simple question like this ― or simply ‘what are you passionate about?’ ― can clue you in on a person’s values, morals, goals and motivation in life. If your date’s answer is ‘my family,’ then chances are that this person is someone whose priority is to build a prosperous future with a partner both emotionally and financially. If their answer is ‘reality TV,’ be prepared to watch a lot of ‘The Real Housewives.’” ― Carin Goldstein, a couples therapist in Sherman Oaks, California 

7. On your last vacation, did you plan everything out beforehand or go with the flow?

“This question reveals a lot about a person’s lifestyle and personality. For many people, having things scheduled or planned will cause anxiety and make a vacation stressful. On the other hand, those who are planners might find an open vacation with no plans to be anxiety provoking. I think this question reveals much about one’s personality because it will mimic a person’s lifestyle.” ― Antonio Borrello, a psychologist in Detroit

8. When you’re old and gray and you’re looking back at your life, what do you want to be remembered for?

“This is a fun one but it also tells you what their priorities really are. Everyone tells you what they’re doing currently in their life (I’m an accountant or in grad school, for instance) but that doesn’t really tell you where their priorities really are. This one gets to the bottom of it without it seeming like an interrogation.” ― Aaron Anderson, a couples therapist in Denver

9. What dating advice would you give the high school version of you?

“You learn about how the person has grown with this question. You also get a sense of how the person sees him or herself then and now, and what could be improved.” ― Diane Spear, a couples therapist in New York City

10. What is the most awkward/embarrassing thing that’s happened to you recently?

“Ask this to see how willing they are to be vulnerable and humble and if they have a sense of humor. If they are able to laugh at themselves, then it’s likely they will be easygoing when you take a fall.” ― Kristin Zeising, a psychologist in San Diego 

11. What’s your philosophy on tipping?

“People who are generous tend to make better partners. A similar question might reference volunteerism!” ― Tom Murray, a couples therapist in Greensboro, North Carolina

12. What’s your favorite thing about your best friend?

“This question gets at a person’s value for close, ongoing relationships and the role they play in their life. Listen for what they like about these people, how they engage with them and how much they smile, and you’ll get clued into what they are looking for in a partner without asking so directly. You’ll get a great sense of what kind of friend and what sort of value they put on keeping those relationships strong.” ― Alicia H. Clark, a psychologist in Washington, D.C.

13. If you had a dinner party and had to invite a musician, a politician, a famous couple and only one family member, who would you invite? Bonus points: What would you be serving, where would you have it, and what would be on your dinner playlist?

“This question assesses a person’s creativity and personality. As you are getting to know someone, it’s important to assess interests, values, political views, and how they interact in social settings. It also allows you to see how they use their imagination, which can be helpful later on in romance and sex.” ― Shannon Chavez, a psychologist in Los Angeles

14. What’s your biggest pet peeve in a partner?

“On a first date, we all put our best foot forward, but this question can cut through the facade and invite them to give an authentic response. They don’t like messiness and you’re a slob? We may have a problem. They despise country music and so do you? Still in the running.” ― Ryan Howes, a psychologist in Pasadena, California

15. How do you spend your free time?

“Many people don’t have ‘hobbies,’ so this question is less likely to make someone feel like their answer needs to be special or impressive. There’s enough of that kind of pressure on a first date. Their answer could be spending time with friends or scrolling through political blogs. Regardless, it’s a nice picture into their life on the day to day.” ― Marie Land, a psychologist in Washington, D.C.

16. If you won a $20 million lottery, what would you do with the money?

“Simply put, this question may reveal a person’s value system and help you discern whether your date is self-absorbed, or generous and caring.” ― Jeannie Ingram, a couples therapist in Nashville, Tennessee


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