11 Questions You Should Never Ask A 20 Something Woman On A First Date

Twenty20 / rosslynn
Twenty20 / rosslynn

1. Are your boobs real?

When a woman catches you looking at her boobs on the first date, that’s one thing, but asking this question, just don’t. And no, you cannot touch them.

2. Where did you get that top?

Are you asking because you want to borrow it? Complimenting her top is nice, but asking where it’s from is a bit weird.

3. Is that your natural hair color?

If it isn’t will you even care?

4. So how much money does that pay? (Referring to your career)

Are the amount of zeros in her paycheck dependent upon whether or not she’ll see you again?

5. How many people have you slept with?


6. How long was your last relationship?

Let’s not talk about exes on the first date. We can ride that emotional roller coaster some other time.

7. What’s your ideal guy like?

If she tells you are you going to pretend to be him? She wants you to be yourself, not the guy you think she’ll like.

8. What’s your bra size?

See question 1. Way too aggressive, way too personal, and whatever your guess is, it’s most likely wrong.

9. Do you want children?

This is a very important question, but NOT for a first a date. She just met you, she most likely doesn’t want to think about carrying your child just yet.

10. When do you see yourself getting married?

Another very important question, but don’t assume that every woman WANTS to get married, and don’t ask her on the first date when she plans to. She will have a wedding date on her calendar when she is engaged, until then don’t try to make her feel like her love life needs a schedule.

11. Do you have sex on the first date?

If she does, and wants you to be apart of that, she’ll make sure you know. Thought Catalog Logo Mark

Writer based in the Philadelphia area. Person who really loves her dog and watching cooking shows. Check out my writing on Thought Catalog and follow me on Facebook! Connect with me and submit your work on Collective World.

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