Terrible Questions Never to Ask on Your First Date

Alejandra Rodríguez
3 min readSep 6, 2022

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First dates are nerve-wracking. You have to make a good first impression, and at the same time, must not come out too strong. Everything must also be perfect: the place, the food, and the ambiance.

On top of all these, you have to ask the right questions. You don’t want to come out offensive or rude by asking the wrong ones. If you do, you won’t get a second date.

To avoid driving your date away, here are five of the worst, no-go questions you should steer clear from asking on a first date:

Why are you single?

Asking a woman why she’s single is outright rude. It may imply that something’s wrong with her; that she’s single for a negative reason. You may not mean it that way, but she might misunderstand.

It sounds harmless, but asking about it will make her uncomfortable. She doesn’t want another person to question her life decision.

If she wants to talk about it, she will open up. The same goes for asking about her previous relationships or sexual partners.

Do you always wear this much make-up?

Don’t comment about her appearance if it’s anything but nice. Whether it’s her make-up, her dress, or her skin color.

You may not like her make-up, but that woman spent hours just to look good. She prepared for your first date. Besides, putting on make-up isn’t always to impress you. It may be her way to gain confidence. Don’t ruin it for her.

The same applies to her skin color. Be sensitive enough and refrain from commenting about skin preferences or race. You would not want to offend her or be called ‘racist’.

Do you normally eat this much?

Aside from implying that she eats too much, you’re also indirectly saying your preference for skinny women. Women are sensitive when it comes to weight. So the question will deeply hurt her feelings.

Be glad if a woman eats on your first date. This means she’s comfortable with you. Don’t kill the mood by asking this rude question. It won’t only make her self-conscious, but also worry about the bill.

How much money do you make?

In case you forget: You’re on a date, not on a transaction or business meeting.

While it’s okay to talk about your careers on the first date, try to draw some lines. It’s okay to ask about what she does or her line of career. But don’t go overboard and ask about how much she’s earning.

It’s inappropriate and would make the conversation awkward. She may also think you’re interested in her money more than her. Basically, anyone who gets asked about their salary would feel uncomfortable and hesitant to answer it.

Don’t make comments about her career or job preference, too. Avoid judging her work or saying she could do better. Instead, express interest in what she does in a way that you’ll get to know more about her.

Do you love me?

If you’re doing that to hook her up, don’t. She will not fall into your bait.

Instead, she will freak out. She will think you’re onto something because you’re moving at a brisk pace. You might as well not hope for a second date because she will dodge it.

Serious men take their time to build relationships. They don’t just ask uncomfortable questions out of nowhere on first dates, so be mindful. Good luck!

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