There are two schools of thought about first dates: Play it super cool, or go deep. If you're apt to try the second route, there are certain personal questions to ask on the first date. I mean, if we all put our heads together, we could probably think of about a thousand. But I asked a slew of relationship experts to each pick one serious question they'd advise you ask on your first date with someone to get a better idea of who they are, and compiled them into a succinct list of 11 ideas, from questions about deal-breakers to ones about what really makes them happy.
I have historically gone more in the direction of the first path, keeping things pretty light on a first date. That being said, if you're the type to go there on a first spin with someone new, these queries are solid things to ask off the bat, and will certainly guarantee an interesting conversation. You'll find out a lot more about your potential partner than you normally would, and you won't waste any time with small talk or vapid questions about work or the weather, and no one will be staring quietly into the guacamole. One thing is for sure: You won't be bored.
1. How Do You Get Along With Your Parents?
The best first-date question: "What is your relationship like with your parents?" zen psychotherapist and neuromarketing strategist Michele Paiva tells Bustle. This can be extended to relate to exes or anyone, she says — it's just as valid to ask about your date's relationship with their former lovers and parents as it is to talk about their friends or even their professors or mentors. "[This] tells you a lot about how they handle adversity," Paiva says. Find out now, or forever hold your peace …
2. Do We Share The Same Deal-Breakers?
"Ask about one of your deal-breakers," life coach Kali Rogers tells Bustle. When she says "one," she really means one: "You don't have to ask them all at the same time, but start with the most important one first," she says. "It might seem embarrassing or too personal, but there's no reason to waste your time or theirs. Plus, if they are in agreement with your deal-breaker … it won't seem too intense and you'll know if a second date is a good idea."
If you find out that "yes, they want kids one day," she says, and you do too, at least you know you're on the same page.
3. What Do You Want?
"While it might seem taboo, you do want to ask the question, 'What are you looking for in a relationship?'" BetterHelp telehealth counselor and psychologist Nikki Martinez tells Bustle. "While some might argue this is early, I would argue that this lets you know what page each of you are on, and if they are likely going to be headed in a similar direction, at a pace you can live with." So find out if they're looking for something no-strings attached, or if they want a relationship, or what. And be sure you feel they're being genuine.
"You want to make sure that you have your radar up to know if the answer that you are getting is authentic," she says. And once you have your answer, think about whether it's an answer you like. The whole point here is to try someone out. "You are getting to know them, after all," Martinez says. If you feel they're being real with you, is their answer one that you can live with? If so, try a second date.
4. Are You Dating Around?
"The truth about this one should be told, especially if someone comes out and asks," relationship coach and psychic medium Cindi Sansone-Braff, author of Why Good People Can't Leave Bad Relationships, tells Bustle. If you need to know upfront, the first date is as good a time as any, she says. "Whether you're looking for a committed relationship or not, this is an important question to get out in the open," Sansone-Braff adds. "If you're both looking for fun and games or a hookup, then this was a first date made in heaven, and it doesn't really matter if you're both seeing other people."
But the flip side isn't so groovy. "If you're looking for a committed relationship, but this other person isn't ready for that, and lets you know that he or she likes playing the field and isn't ready to settle down, then this might be a deal-breaker for a second date." This is great to know, though.
"Don't think you're going to change this person's mind, or that you can sell them something they aren't in the market for," she says. Knowing you have differing needs might be annoying in the short-term, but you'll be glad you knew right away in the end. "Being honest with your desires and intentions from the start will save the two of you a lot of heartache later on," she says.
5. How Do You Have Fun?
"The one thing I suggest to ask on a first date is, 'What do you do for fun?'" Rob Alex, who created Sexy Challenges and Mission Date Night with his wife, tells Bustle. "I feel it is important to get a feel on the first date as to what the person you might possibly get into a relationship with considers fun." If they're all about Netflix and you love taking long runs in the park, you might be on different wavelengths. This question "can go a long way to helping you see a bigger picture in your relationship," Alex says.
6. Do You Have A Dog?
To keep things a little lighter, talk about cats or fish. "A great conversational starter is whether or not your date has a pet," relationship coach and psychic medium Melinda Carver tells Bustle. But it's not just light fodder. "This is important to learn because you may have severe allergies to pets, or you may dislike animals in the house or sleeping in your date's bed," she says. "There are hundreds of stories of people that dislike animals that begin to date someone that does have a pet, and they want that partner to remove the pet from their home or life." Well, that's horrible.
7. How Do You Find Fulfillment?
Ask your date, "What gives you meaning?" Dr. Ramani Durvasula, author of Should I Stay or Should I Go: Surviving a Relationship With A Narcissist, tells Bustle. "It's heavy, but if a person can't answer that, then it is not likely to be that deep a ride." It's not as potentially off-putting as getting deep into deal-breakers, too — this questions could just inspire a really great conversation. "It can be anything — their kids, their family, their art, their job, their surfing, their time with friends." Find out, and remain open.
The only problem comes if they can't answer at all. "If they can't tap into this, then it may not worth step two," she says.
8. What Are You Most Proud Of?
Find out what your date feels most accomplished about. Ask the question, "What is your greatest achievement?" Salama Marine, psychologist and online dating expert for dating website EliteSingles, tells Bustle. "This is a good opening personal question to discover something about the person you’re seeing without them being able to show off too much." And you can share your own stories, which'll be a nice way to talk to someone new.
9. What's Your Marriage History?
You could ask, "Have you ever been married?" New York–based relationship expert and author April Masini tells Bustle. "If the answer is yes, find out if they’re divorced." If not, know that you're in a tricky sitch. "I hear from lots of people looking for relationship advice because they don’t understand that separated is not divorced. It’s married." This might mean entering into a partnership that is fraught with issues.
"His wife is going to be more interested in his doings if she’s still married to him than if they’re divorced," Masini says. "You can feel divorced and act divorced and even look divorced — but unless you’ve legally sealed that deal, you’re married." Don't just figure it'll work out. "Ask. Don’t assume," she says.
10. Do You Want Children?
"If you are over 35, I think it's fine to find out if a person wants kids or not," Stefanie Safran, Chicago's "Introductionista" and founder of Stef and the City, tells Bustle. It doesn't have to be a desperate-sounding plea, but you can easily broach the topic of children and see how they react. You can even just point to a cute kid nearby and find out how your date responds. Less is more here, but it's worth bringing up if need be.
11. What Does Happiness Look Like For You?
Just ask, "What makes you happy?" Tina B. Tessina, aka Dr. Romance, psychotherapist and author of Love Styles: How to Celebrate Your Differences, tells Bustle. It's simple. It's succinct. You'll find out if you're compatible in many ways. And it'll spark a great conversation.