The 20 Questions You Should Never Ask On a First Date

There are usually two kinds of first date: The ones that flow magically—where the time passes so effortlessly that the restaurant has to remind you that they're closing—and the ones that are… well, less smooth. Obviously, the first type of initial meeting is ideal, but a less graceful first encounter doesn't necessarily mean all hope is lost. In fact, along as everything goes fairly well, there's potential for a second date, which could potentially turn into a more serious connection.

But there's one way to make sure that never happens: Asking the wrong questions on date number one. Avoid these twenty queries at all costs and you'll be well on your way to scoring a repeat meet-up. And for advice on what you should actually be saying, refer to The 10 Sexiest Things to Say to Her On a First 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!" Plus, being this skeptical about your potential mates is actually one of the 15 signs you should definitely be single.

"What purpose does this ever really serve?" asks Jessica Elizabeth Opert, a dating and love coach. Generally, it just becomes a bashing session of all the various apps and sites that are out there. "It doesn't really add anything to the experience of your first date," she points out. Also filed under this category? "How are you liking (insert name of dating service here)?" It brings nothing helpful to the conversation. And if you're making The 12 Biggest Dating Profile Blunders Men Make, you definitely shouldn't call attention to it.

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 A, a certified matchmaker and dating coach at Toronto Wingwoman. 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.

"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 pretty weighty question lay on someone you just met.

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." Even when you're in a relationship, if you have separate finances you shouldn't feel obligated to tell your partner the price of something you spend your own money on—in fact, it's one of the 13 secrets you should always keep from your partner.

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 Dr. 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."

Or any other question related to your appearance. "These are loaded questions and you may not be happy with the answers," says Rosalind Sedacca, a dating and relationship coach. 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," she says.

"First dates should be all about getting to know someone on a lighter note," says Lisa Ronis, a matchmaker. "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 awhile before asking. And so many times, the topic comes up organically."

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It might seem like asking this up front 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 really does have true deal breakers, they'll tell you about them in their own way.

"The subject of parents can strike a chord with people and make them uncomfortable," says Perry. "This is particularly true if they aren't on good terms or don't have parents. 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." On the flip side of this, though, is how to tell your partner's relationship with their mother is actually a problem: These are the 6 Signs His Relationship with His Mother Is a Total Deal Breaker.

If you're using this language to ask a person about their race or ethnicity, maybe don't. "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.

"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.

This is maybe seen as an endearingly awkward comment, but it can come off badly. "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. "They don't know you, so they don't know the jokes from the truth." Save these types of comments for when you've spent a little more time together.

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."

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. Also, when you ask this question, it can sound like you're hoping to find out what they want so you can play that role. It's best to let it happen authentically."

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?!"

While you might think you're subtly gauging their financial situation, you're actually just being rude. "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.

"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 like a jerk.

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 is a loser and it's a red-flag which screams they should be avoided at all costs. They obviously have no tact," he says.

Okay, so it's not technically a question, but the question is implied. "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." Opening up first is also a good way to move toward topics you're interested in discussing—making this kind of "power play" is one of the 7 Expert Dating Tips from Silicon Valley's Top Millionaire Matchmaker.

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