Worst First Date Questions

Asking how many people someone has slept with is very personal. This question often makes someone uncomfortable, no matter the answer.

Do not ask this question on any date. Especially not the first one.

Asking about money early seems shallow. It suggests you care more about a date's bank account than their personality.

This question may hit your date's insecurities about being single. It almost suggests something is wrong with them.

Does this question need an explanation?

Wait. If you are on a first date, wondering about the future of the relationship is too presumptuous.

How often do you share your 'deepest secret' with someone you don't know well? The answer is probably 'never.' This question pushes the talk toward awkward ground.

If your date has debt, they will likely feel uncomfortable discussing it with someone they do not know well.

If your date wants you to know this sensitive information, they will tell you on their own time.

This question is too personal. It can sound judgmental.

This topic is too personal and sensitive for a first date. Avoid asking about exes early on.

This political issue can end the date right away. If political alignment is a dealbreaker for you, maybe save it for later. You can still talk casually first.

Asking about kids is tempting if you have strong feelings. Getting this dealbreaker out of the way quickly might be good, but it is a heavy topic. Save it for a later date once you both feel more comfortable.

This question sounds disturbing. Ask, 'Do you have roommates?' or something similar instead. This avoids sounding like a stalker.

Talking about major life regrets over coffee is unlikely to be what your date wants.

Many people get scared off if you ask about big commitments on the first date.

Asking this question makes you sound either too arrogant—seeking someone to praise you—or too insecure—needing someone to tell you what you like. Neither approach sets a good tone.

This question is a big risk. If your date has a good family relationship, they will likely want to talk about it. If they do not, you bring up painful memories with one sentence. Let them lead with what they choose to share about family.