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The 25 Questions You Should Never Ask on a First Date

Relationship experts say these questions are not likely to get you a second date.

First dates, albeit nerve-wracking, can also signal the beginning of an exciting new relationship. So, of course, you want to make a great first impression—and this includes asking the right questions. You'll want to stick to topics that are respectful and will hopefully spark further conversation. And you'll want to avoid anything that's inappropriate, prying, or makes your date feel like they're on a job interview. To give you some help, we spoke to relationship experts about the worst first date questions.

RELATED: 20 Red Flags Your Partner Can't Wait to Break Up With You.

Why are you still single?

Woman on a bad date

There are so many things wrong with this question.

"For starters, it presupposes that there is something wrong with being single," says Rabbi Shlomo Zalman Bregman, an author and matchmaker. "Beyond that, it's quite possible that a person hasn't met their soulmate yet, and that's why they're not in a relationship. If you're on a date and realize that you're sitting across from someone who seems amazing and is still single, don't ask them why. Simply be happy about it!"

What dating apps are you on?

first date tips: don't ask this question.
Dusan Petkovic/Shutterstock

"What purpose does this ever really serve?" asks Jessica Elizabeth Opert, a dating and love coach. "It doesn't really add anything to the experience of your first date."

Generally, it just becomes a bashing session of all the various apps and sites that are out there. Also, filed under this category: "How are you liking (insert name of dating service here)?" It brings nothing helpful to the conversation.

You're not crazy, are you?

Man talking too much on a date

Followed by something like, "I've been meeting a lot of crazy people lately." Yikes.

"Though this might sound cute, it can come off as strange to your date," says Candice Alstar, a certified matchmaker and dating coach. After all, they might start to wonder why you're meeting so many crazy people in the first place.

"It's best instead to focus on questions that actually help get to know what your date is about," she advises.

Where do you see this relationship going?

sad young black woman and young white woman sitting on the dock at a lake and not looking at each other

"This always makes the person asking it look desperate, foolish, and in a rush, while annoying or stressing out the person to whom it is asked," says Bregman. To be fair, it is a pretty weighty question to lay on someone you just met.

RELATED: 8 "Small But Toxic" Things to Stop Saying to Your Partner, According to Therapists.

How much did that cost?

A bored-looking young woman sits at the table having a coffee with a man.
Dean Drobot / Shutterstock

Nope nope nope. Whether it's their apartment, watch, or a clearly luxe handbag—it's none of your business.

"It's just plain tacky, and also will make you appear shallow and only concerned with money," says Bonnie Winston, celebrity matchmaker and relationship expert. "You can compliment something without wanting to qualify it with a price."

Are you seeing anyone else?

Couple Disagreeing at Dinner
Volodymyr TVERDOKHLIB/Shutterstock

This question implies a more intimate question: Are you having sex with anyone else? And the first date is simply too soon to be asking about this.

"Anytime you bring up sex early in a relationship it can be seen as intrusive or as if that's the person's only interest," notes Venessa Marie Perry, founder and chief relationship strategist at The Love Write. "The topic of sex isn't something that should be taken lightly or brought up too soon."

Do you like my outfit?

young red-haired woman sitting in a cafe with friend and talking about something.

Avoid this or any other question related to your appearance.

"These are loaded questions and you may not be happy with the answers," says dating and relationship coach Rosalind Sedacca.

Emma Hathorn, dating expert at, adds that asking about being over or underdressed is a no-no: "You should always seek to be an individual. Dress to your personality, your character, and your taste. If your date doesn't like that, then that's on them."

Do you want to have kids?

man and woman thinking of fun questions to ask each other during a first date

"First dates should be all about getting to know someone on a lighter note," says matchmaker Lisa Ronis. "These questions should be raised down the road. I have clients who are caught between a rock and a hard place because they don't want to waste time, but I advise them to wait until they know the person a while before asking. And so many times, the topic comes up organically."

RELATED: How Long It Actually Takes to Get Over a Relationship, According to Research.

What are your deal breakers?

male gay couple sitting at a dining table with serious looks on their faces.. Real people. Real couple.

It might seem like asking this upfront could save you some time, but it can backfire.

"This question comes off as though you're trying to find out what the other person likes so you can either pretend to be that or decide immediately if they are worth your time," says Celeste Headlee, a radio host, journalist, and author of We Need To Talk: How to Have Conversations that Matter.

Chances are, if someone does have true deal breakers, they'll tell you about them in their own way.

What's your family like?

couple getting to know each other on a first date
Rommel Canlas/Shutterstock

Barbie Adler, the founder and president of matchmaking service Selective Search, notes that family is a complex topic, uncomfortable for some but a source of joy and support for others. "It is by no means off-limits, but it should be approached with care," she says.

"This is particularly true if they aren't on good terms or don't have parents," adds Perry. "In addition, people automatically assume if you don't have a good relationship with your parents, then you have mommy or daddy issues, which may not be the case."

What are you?

Couple talking seriously outdoors in a park with a green background

This type of language should be avoided if you're using it to ask a person about their race or ethnicity.

"Newsflash: We are all humans," says Michelle G, a certified matchmaker and dating coach. If someone wants you to know about their race or religion, they'll tell you.

Another area to avoid? "You definitely don't want to put someone on the spot by asking if they have dated other people of your race or religion on a first date," Sedacca says.

What do you want to do tonight?

couples drinking coffee- signs hes not into you
bbernard / Shutterstock

"Trust me, a date appreciates it when you've made plans," says Headlee. "If you ask where they want to eat, it often sounds like you've put no thought or preparation into that all-important first date."

If you're not going to set a destination before meeting up, at least come armed with some options and ask what they'd prefer.

RELATED: 5 Things You're Not Texting Your Partner That Therapists Say You Should Be.

Do you drink a lot?

Waist-up view of men sitting at outdoor table in afternoon sunlight, holding glasses of red wine by the stem, and examining color and clarity.

The topic of drinking can be sensitive for people, so spotlighting it can make them feel obligated to share something personal. It can also make you seem like you value drinking more than you do.

"You probably don't drink as much as you think, and discussing topics like this even as a joke can come across wrong if someone doesn't know you yet," Candice A. explains.

Why did your last relationship end?

bored woman date
Mladen Mitrinovic/Shutterstock

No matter how curious you are, "do not ask about previous relationships, especially not about the dynamics of their divorce or recent breakup," advises Sedacca. "It's really none of your business at this stage in the relationship to know the gory details of their breakup or how many people they've had sex with since their divorce."

What are you looking for in a relationship?

Middle aged male gay couple eating dinner in a restaurant

This is yet another topic to be saved for later on down the road.

"There's no need to put that kind of pressure on the other person," Headlee says. "Let them enjoy the first date without worrying about next steps. If they want a second date, you will know, believe me. If they don't, it's best to make it as easy as possible for them to walk away kindly and happily."

How many people have you slept with?


This question is never really appropriate, but especially not on a first date. "This is none of your business," Bregman points out. "It is private, personal information. Why should it be revealed to YOU, a complete stranger, who they may never see again?!"

Do you own your house?

Unhappy middle-aged distanced couple on bench
Erickson Stock / Shutterstock

While you might think you're just making conversation, you're actually subtly gauging the other person's financial situation.

"A lot of people keep their cards close to the vest at the beginning—as they should," Ronis says. Trying to figure out how much your date has in their bank account is never a good idea.

RELATED: 7 Body Language Signs That Mean Someone Is Attracted to You, According to Therapists.

What's your favorite sex position?

Man looking skeptically at woman

"If you're looking to not have the second date, this is a great way to kill any possibility," Michelle G. says. "Maybe you thought this would be funny or a great way to break the ice—wrong." It's pretty much impossible to ask this in a way that doesn't make you look bad.

Suzannah Weiss, relationship coach and resident sexologist for the pleasure product brand Biird, adds that this can come off as presumptuous since you're assuming you'll be having a sexual relationship with the other person. "It is great to communicate about sex, but only once it's clear that both of you want to have sex," she says.

Do you always eat/drink this much?

Unhappy Woman on a Date

This one should be self-explanatory, but Bregman says he has heard of people asking this on first dates before. The reasons they give? Everything from wanting to gauge how much things would cost if they ended up together to liking thinner partners in general.

No matter the reason, "any person who asks this… should be avoided at all costs. They obviously have no tact," he says.

What was your ex like?

People on a bad date

In general, asking about someone's ex on a first date is a bad idea.

"It's best to treat first dates as a clean slate for the both of you," advises Adler. "Knowing about a person's past relationships before developing your own relationship with them can lead you to make biased assumptions about them based on limited information. These topics should only come up later in the relationship when you know the person well enough to interpret their past decisions in light of who they really are."

RELATED: If Your Partner Is Asking You This One Question, They Could Be Cheating.

Tell me about yourself.

Young Asian woman on date with boyfriend
BigPixel Photo / Shutterstock

Okay, so it's not technically a question, but the question is implied—and it can make your date feel like they're on a job interview.

"This is an overwhelming statement that typically causes an awkward pause," says Michelle G. "The best approach is to ask what you want to know."

What do you like to do?

bad date bad tipper
djiledesign / iStock

While learning someone's favorite things to do can help you get to know them, this question is a bit too broad. "More specific questions tend to yield more interesting and personal answers," explains Adler.

"Picking up on your date's comments and behaviors and basing your questions off of these can yield more generative conversations: For example, noticing them humming along to a song in a public place can be a good segue into a conversation about music, and the dish they order in a restaurant can be an entry point into asking about their favorite type of cuisine, or even their past travels," says Adler.

Why did you swipe right?


This is essentially the equivalent of fishing for compliments. Weiss says they might not remember exactly why they swiped right on you and it can put both of you in an awkward position.

"Also, initial right swipes are often about looks, so it comes off like you're basically asking them to validate that you're attractive," says Weiss. You can ask this question further down the line, or Weiss suggests telling them why they stood out instead.

What's your biggest regret?


Adler says it's not uncommon for people to ask these types of deeply personal questions on a first date, however, you should try to avoid them: "Most often, it simply comes off as invasive or even rude, and can make your date feel awkward or interrogated."

Conversations like this are hard, and when the time is right, or you feel comfortable with the person, then you can share those more intimate details. "This is not to say that first dates cannot enter into this kind of deep territory—they certainly can—but it should happen organically, in a way that is comfortable for both of you, rather than being forced," says Adler.

Why don't you want to see me again?

confused woman looking at man
Shift Drive / Shutterstock

If the date ends with them expressing that they don't want a second date, the worst thing you can do is ask why. "It puts them in an awkward position because there's almost no way to respond to this question that does not come off insulting," explains Weiss.

"It also puts you in a position to hear what somebody else dislikes about you—which will often reflect their preferences and perceptions more than any actual flaws of yours," Weiss adds.

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Courtney Shapiro
Courtney Shapiro is an Associate Editor at Best Life. Before joining the Best Life team, she had editorial internships with BizBash and Anton Media Group. Read more
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