- Making small talk on a first date can get awkward — especially if you ask the wrong questions.
- Business Insider spoke to seven relationship experts and found out their least favorite first date icebreakers.
- Their off-limit questions ranged from "Why did you and your ex breakup?" to "Do you always wear this much makeup?"
- Visit Business Insider's homepage for more stories.
First dates can be a communication minefield.
On the one hand, you want to present the best version of yourself to someone who could potentially be your boyfriend or girlfriend. You want to get past the awkward "small talk" and figure out whether the two of you are compatible.
Read more: 7 relationship experts reveal their favorite questions to avoid awkward small talk on a first date
But on the other hand, you don't want to get too invasive. While there's no set rulebook for how to act on a first date, there are some questions that could give your potential partner the wrong impression. Business Insider spoke to seven relationship experts and found out their least favorite conversation starters, ranging from asking about an ex to bringing up sex too soon.
Here are the seven worst questions to ask on a first date, according to relationship experts:
SEE ALSO: 7 relationship experts reveal their favorite questions to avoid awkward small talk on a first date
SEE ALSO: 13 simple ways to get better at small talk
What's your relationship like with your parents?
Relationships experts say to stay away from overly personal questions on the first date.
Asking people invasive questions regarding their relationship with family and friends gets too nosy, says Rori Sassoon, a relationship expert based in New York City. "That's just so personal, number one, and it's not your business, number two," Sassoon told Business Insider.
If you're not sure if something is too personal, you can ask your date if they mind sharing, Shira Teichman, a dating coach and cofounder of the dating app Forj, told Business Insider. While Teichman understands many people want to skip the "small talk" and get to a deep conversation, you must ease into these topics so the other person does not become uncomfortable.
"You can't 'fast-track' emotional intimacy; relationships need to unfold in their own time and in their own way," she said.
Why did you and your ex break up?
Bringing up past relationships can also ruin first dates, experts say.
Some people might be curious about why their date broke up with an ex in order to spot potential red flags down the road, New York City-based love coach Susan Winter said. This question is problematic for multiple reasons, however — including the fact your date likely won't be honest with you.
Plus, what happened in the past isn't relevant to the date that's happening right now. While someone may have had a rocky relationship with their last partner, you could bring out a completely different side of them.
"Sometimes we are different versions of ourselves with different people," Winter told Business Insider. "There are people who bring out the best in us, and there are people who bring out the worst in us."
What's your favorite position?
Avoid talking explicitly about sex on the first date, says Marla Mattenson, founder and CEO of a relationship consultancy. (The one "correct answer" here is "CEO," if someone actually asks this, Mattenson added).
Sassoon said men especially tend toward getting too sexual too fast. "They can be a little more inappropriate," she said. "It's a little too much, too soon."
How can you work in a job like that?
Avoid judgmental comments and questions about what someone does, wears, hangs out with, etc., says Andrea Syrtash, a dating expert and co-author of "It's Okay to Sleep With Him on the First Date: And Every Rule of Dating Debunked."
"You don't want your date to feel like you're keeping score and auditioning him or her for the future," Syrtash told Business Insider.
Why weren't you a better friend?
Along with judgmental questions, avoid asking things that would make your date feel guilty about a personal story they revealed to you, says relationship coach Sami Wunder.
"Remember, the point is to feel good," Wunder said.
These kinds of comments can suggest a negative attitude that will lead to problems down the line.
"You can tell when people have a negative attitude if they are judgmental or making fun of the people around them, if they are curt with the waitstaff, or if they're complaining," Winter said. "[You] just don't need that negativity."
Do you always wear this much makeup?
Mattenson says to avoid asking a question about someone's appearance.
In fact, don't say anything about your date's appearance unless it's a direct compliment, Miami-based matchmaker Claudia Duran told Business Insider. Even if your date looks different in real life than they do in their photos, or if you don't want to see them again, Duran says to still be kind.
"If there's nothing nice to say, be respectful and don't say anything at all," she added.
Do you want a relationship?
Don't inquire about a long-term relationship on the first date, Duran says. While you should be upfront about whether you just want to hook up or would like something more serious, getting too serious too soon turns your date off.
Even if you are looking for someone to get serious with, "no one likes to be asked on the first date," she said. "It's too early to say."
Plus, you yourself should not decide whether you or not you want to date a person after just one date. Just as if you were a job candidate looking for a new gig, you don't know if the first place you interview at will work out.
"You go and you look and you talk to the people and you look at the corporate culture and you kind of get a feel for whether this job would be right for you," Duran said.