20 Questions a Man Should Never Ask a Woman (and the Reasons Why)

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by  Dean Stephens | Last Updated: 

Better to remain silent and be thought a fool than to speak out and remove all doubt. Abraham Lincoln

If there’s one thing that most men eventually learn in life, it’s that sometimes it’s better to say nothing at all.

And this lesson is arguably best applied when it comes to asking women certain questions. You may have already realized this the last time you asked a girl how old she was—or worse, how much she weighed.

We’ve all been there. You’ve dropped the first question that (for whatever reason) came to your mind and, were met with daggers / a drink to the face / a kick to the shin (pick your poison).

To be clear, we’re not telling you to ramp up the awkward silences. When it comes to questions you should ask women, you’ll find 120 of them right here.

Rather, every man should be aware of the questions which will not add any real value to your interactions.

As usual, gentlemen, we’ve taken care of the legwork for you. Here are 20 questions you should never ask a woman, in no particular order.

1. Can I kiss you?

It’s generally not a good idea to ask her before going in for the kiss. 

Assuming you’re on a date and that the circumstances are right, it’s ‘less square’ to just go for it.

Why?

First off, there are plenty of ways to test the water without vocalizing the request (raise a hand to her cheek and brush her hair out of her face. If she pulls back a bit from your touch, you know the kiss is a no-go). 

Secondly, asking for a kiss isn’t necessarily wrong by itself. But it puts you at risk for sacrificing masculine frame

For best results, make sure to test the water with some innocuous touching/flirting first, then go in for the smooth-move when her body language has given you the ‘green light.’ 

2. Why won’t you talk to me?

Post-commitment, this isn’t such a bad question (when posed within the context of you holding masculine frame and checking on her out of a sense of care, responsibility, and boundaries within the relationship—and not out of insecurity). 

But pre-commitment? Asking this question puts you at serious risk of sounding desperate and clingy—neither of which are attractive masculine traits. 

Concentrate on pursuing your own purpose in life, and not caring as much if a woman does or doesn’t want to talk to you. 

A better question to ask would be “You seem quiet today. Is everything ok?”

3. You look different today, why’s that?

If this is meant as a compliment to acknowledge something ‘new’ she’s done (like getting a haircut), then you may be able to pull it off in a teasing, mischievous fashion. 

But if it’s meant as a neg or a put-down, it likely isn’t a good idea. 

Whether she does or doesn’t look different, this question lacks tact and doesn’t really go anywhere meaningful. 

A better question to ask would be something like “I like that dress! Is it new?”

4. You’re looking tired today, did you not get a good night’s sleep?

Calling out a lady’s tired looks (even if she truly does look tired) may hurt her feelings and make her feel like you think she’s unattractive. 

Instead, consider an alternative question. “I’ve been looking forward to catching up with you. Tell me how your last few days have been.”

5. I know you’ve got a boyfriend, but can we be friends?

If you truly just want to be friends, then there’s nothing wrong with this question. Yes, it will make you seem less attractive—but if all you want is friendship, then that shouldn’t matter to you anyway. 

But if you have ulterior motives (i.e. you actually want to sleep with her), then just skip it. 

Here’s the thing. A high value man doesn’t ask for people to be his friends. He naturally attracts friends by being awesome, likeable, and a winner. 

6. How old are you?

This actually isn’t a bad question to ask a woman who looks to be under 25-27, as long as she’s younger than you. 

But if you ask a 30-40+ year old this question, you may run the risk of making her feel a bit self-concious. It may be better to let this one sit until you know each other better. 

7. I don’t know, what do you want to do?

Every girl wants a guy who’ll be the man and lead with a decision.

As the man, the ball is in your court to make a plan. 

You can ask her if she has a preference. 

“Do you prefer movies or concerts?”

But never ultimately put the decision of ‘what to do’ onto her. It’ll make you look weak, disorganized, and apathetic—none of which are attractive traits. 

8. Is that what you’re going to wear tonight?

Implication: “That looks terrible, what were you thinking?” 

Unless your girl is completely off the mark on dress code, this is a risky line to take, boys.

If you feel like you need to correct her fashion choices, you should probably just cut her loose and court a woman who’s more in-line with your style. 

9. Are you pregnant?

This is a risky one, because if she’s not pregnant, you pretty much just called her ‘fat.’ 

Best way to handle this one? Just ride it out and don’t mention anything. If she doesn’t bring it up, you can casually bring up a conversation about your thoughts on having children in the future. 

If she still doesn’t mention it, and if you’re not fond of the way she looks, it’s probably best to move on and date someone else. 

10. How many guys have you been with?

I’m not a huge fan of this question because asking it out of a very specific context can put you at risk of looking jealous and insecure—which is a massive turn-off and a low-value marker. 

There’s one caveat, however. If she asks you the question first, it’s fair game to reverse it. 

11. Is your sister attractive?

This is a risky question. For women, competing for the attention of a dating partner with a sibling feels far worse than competing with a stranger. 

It just hits closer to home, in every way imaginable. 

Whether you’re pre-commitment or post-commitment, stay out of this territory unless you’re willing to risk complete and total disaster. 

12. Are you on your period?

This is a dangerous question to ask because, in her mind, it implies that you’re asking her if she’s ‘available for sex,’ which puts you at risk of sounding desperate and low value (trying to secure the ‘prize’ through agreement ahead of time instead of just making your move). 

It’s also crass and insensitive. 

What should you do instead?

Carry on and make your move as usual. If she informs you that she can’t because she’s on her period, tell her you don’t mind (if you don’t), but be understanding if she’s not down with it—especially if you’ve never slept together before. 

That’s a big step for some women, and being understanding is the right move on your part. 

13. Can I borrow some money?

How to turn a girl off in 5 words. Women seek providers, not parasites.

14. Do you think I’m attractive?

Asking this question makes it sound like you aren’t confident, so it’s a risky one. 

If she’s spending time with you and engaging with you, assume she’s into you. Don’t worry—she’ll bolt soon enough if she’s not. 

15. How much do you weigh?

Chapter two of the gentleman’s handbook. Never ask her how much she weighs.

Either you like how she looks, or you don’t. There’s really no reason that a man would need to ask this one. 

16. Why do you like wearing [insert piece of clothing]?

I’m not a big fan of this question because even if it’s meant well, you run the risk of sounding judgemental. 

Instead, ask something like this: 

“I like that dress. Do you feel like the style matches your personality?” 

17. Are you in love with me?

This question puts you in dangerous territory. You run a serious risk of sounding low-value and desperate. 

Always leave the L-word (and/or bringing up the commitment talk) to her to bring up first. Once she brings it up to you, you can decide if you’re ready for it. 

18. Why are you friends with [insert guy’s name]?

This question definitely puts you at risk of sounding jealous or insecure—both of which are serious low-value markers. 

As a strong, masculine man, you shouldn’t be threatened by other men in her life. This woman is either into you, or she isn’t. You can either trust her, or you can’t. 

If you don’t like her friends, feel like you can’t trust her, or just don’t like how she interacts with other men in-general, bail and find a different woman to date. 

Don’t ever try to come between a woman and her friends or control how she interacts with them. 

On the same token, if you don’t like her friends, you have every right to hit the road and not feel guilty about it. 

19. Why are you single?

This is an interesting question because it’s almost ok, but not quite. 

It can make the conversation sound more like an interrogation than a conversation. 

Instead, phrase it like this (and by the way, this is a question that you SHOULD always ask when you meet someone new):

“So tell me about your relationship history. What kinds of dating and relationship experiences have you had?” 

A high-value woman won’t mind talking about her relationship history in the slightest, as long as you’re willing to return the favor. 

Red Flag Warning: If everything she has to say about her exes is negative (they were toxic, they were abusive, they were all pieces of crap, etc.), then head for the hills. 

Odds are very good that those men were not all bad. The common denominator is likely her.

20. Are you really going to eat that?

Unless this is said in a playful way, hold off on the food judgment.

Instead, ask a question like this: 

“Wow, that dish looks exotic/rugged/spicy. Have you ever had it before, or is this a new experiment?”

Conclusion

When it comes to many of the above questions, context is key. If you’re maintaining a strong masculine frame, have a great rapport with the girl, or are in a relationship already, you may be able to get away with a few of them.

If you’re not the best at maintaining a conversation, you might want to learn about the best topics to talk about with women.

The goal isn’t to stop being playful or teasing. Teasing is a great way to build attraction with a woman and show that you have a sense of humor.

We merely want you to avoid the questions that put you at risk of coming off as low-value, insecure, desperate, etc. 

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