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?

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