In Honor Of The Day Of Stupid Questions — 10 Questions You Probably Shouldn’t Ask On A First Date

Flirtini Blog
3 min readSep 28, 2021

The Day of Stupid Questions is September 28, or it will be because we are making it. So in honor of the day, here are ten stupid questions you probably shouldn’t ask on a first date; well, I guess at least if you want to have a second date.

Why Are You Still Single?

While this may seem like a relatively harmless question, it can imply you are asking your date if something is wrong with them. Remember, some people are happy with being single until the time is right.

How Many People Have You Slept With?

First of all, there is no reason to ask this on a first date unless you plan to sleep with this person that night and are concerned about disease. If that is the case, consider asking if they’ve recently been tested at a more appropriate time.

Where Do You See This Relationship Heading?

If you are asking this question on a first date, you have some serious confidence issues. There is no reason to ask this question unless you have been together for a while and feel like the relationship has stalled. Please just don’t!

Are You Attracted To Me?

Again this seems like confidence issues. Just assume the person you are on a date with finds you attractive, which is why they are on the date with you. Just chill.

You’re Not Crazy, Are You?

Whether or not you think your date is crazy, you should never ask them. If you are worried, just leave. On the other hand, if you ask just to be funny, keep in mind this question can come off as creepy or even rude.

What Are Your Deal Breakers?

When on a first date, remember this isn’t 20 Questions. You don’t need to know what your date deal breakers are right off the bat. Some people’s deal breakers change. You could blow a great opportunity by asking this unnecessary question.

Why Did Your Last Relationship End?

It’s never a good idea to dig into your dates’ past when you barely know them. When relationships end, there are always two sides to the story. Even if they tell you, it may not be the truth. Just avoid this question until much later in the relationship.

Do You Always Eat/Drink This Much?

If this question even pops into your head, maybe you should just leave now. You don’t know what your date’s day was like; they may not have had lunch and are eating to make up for it — another question to avoid.

How Old Are You?

If you don’t know how old your date is, you probably shouldn’t even be on the date, to begin with. However, you should focus on your date’s more important qualities and on getting to know them better as a person.

How Much Do You Weigh?

You should never ask anyone this question unless you are a doctor conducting an exam. While the question may seem innocent to you, it’s actually very offensive. Weight is subjective, and if you don’t like bigger or smaller people, DON’T GO OUT WITH THEM!

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