Awkward questions you should never ask on a first date

What's your relationship like with your parents?

Relationships experts say to stay away from overly personal questions on the first date.

Asking people 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.

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."

How can you work in a job like that?

Avoid judgmental comments and questions about what someone does, wears, hangs out with, etc., said 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.

Do you always wear this much makeup?

Mattenson said 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 said to still be kind.