Dumb Questions Guys Frequently Ask

So you want some awkward questions to ask a girl? Well, whatever your motivation is, there are a lot of questions that girls will find awkward, so even if you are just here to do some research for what NOT to say, this list could prove very useful for you! Some of these questions might be better classified as “annoying” but I threw them in here all the same. These are designed to be questions that any guy might ask any girl, not specifically two people in a relationship. Generally speaking, any question which plays on a girls insecurities, such as weight, sex, looks, will end up being awkward. And remember to be prepared. If you have an awkward question to ask a girl, it may end up being just as awkward for you too.
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Onto the awkward questions to ask a girl…
Awkward Questions to Ask a Girl
What’s your bra size?
Depending on the girl, this might not be that embarrassing, but I think the whole concept of expecting her to tell you is awkward.
What’s your most embarrassing moment?
If it is really embarrassing she might not tell you though, but quite awkward if you are expecting an answer.
Is your sister/friend single?
If the girl you are asking likes you herself, I can’t think of a more awkward question than this, although in another situation she might be trying to set the two of you up.
Does your friend/sister like me?
Basically the same as above but with the added pressure of her having to know what her friend/sister thinks.
Do you like me?
Awkward! Even if she does like you, how is she supposed to answer on the spot like that?
Am I your type?
Similar to the above question, but if you aren’t her type, it is hard for her to answer, and if you ARE her type, even harder- just wait and see!
How many guys have you been with?
This is probably acceptable to ask if you are in a relationship and the discussion is going that way, it is still going to be awkward though.
Why are you single?
I find this question just comes out sounding like “What’s wrong with you? There must be something”
Have you ever been with a girl?
I think the assumption guys like to make that all girls have been with another girl while experimenting at college can cause a lot of awkwardness for girls, some of them might even feel bad that they haven’t since they get asked it so often.
Why don’t you go out much?
Again, this sounds like you are suggesting there is something wrong with a certain behavior and can be an awkward question to answer.
Why do you go out so much?
You may as well ask “Are you a slut??!” You might want to word this question differently.
Are you on your period?
If a girl is angry, and you make the suggestion that she must be on her period, what do you think is going to happen to those anger levels? The suggestion that she is only angry because of her period is just going to make her more angry, regardless of the validity of the question.
What’s your sexual fantasy?
Chances are, she doesn’t want to tell you this, so now she either has to make up a fantasy that you will associate with her forever (awkward!) or she has to lie and say she doesn’t have one. Or just tell you her fantasy.
Why don’t you dress like other girls?
Or you could just say “Are you weird?”
Why did you and your ex break-up?
I hate questions like these, it is clearly fishing for more information like “Did you cheat?”. This question brings up a lot of potential pain, and you are very unlikely to get the real reason anyway, so just avoid it. Unless you WANT to make her feel uncomfortable, in which case, go for it.
Random sexual questions like “What’s your favorite position?” “Do you spit or swallow?”
Most girls don’t like discussing topics such as this so freely, maybe with their best friends but not with guys, they don’t want to appear slutty, or they just don’t want to tell you personal things, and some will be disgusted just by the words used.
What underwear are you wearing/What color is your underwear?
This might not be such a big deal depending on the girl, but they might still feel awkward knowing which way you are trying to steer the conversation.
Tampons or Pads?
This question is just going to be awkward for the guy as well as the girl, in fact, anything period related will probably be pretty awkward.
How much do you weigh?
Remember what I said about questions that play on her insecurities as being awkward?
Which of your friends would you have a threesome with?
Probably “none” by all means, but make her answer anyway if you want to make things awkward.
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Temi Badmus
Temi Badmus
Temi Badmus is a Food scientist and an Art enthusiast. Her desire is to give a listening ear to people and to give an opportunity for everyone to be heard. Has any one told you that you are special? Yes, you are. You were beautifully designed, you are relevant to this generation and very special to me. Connect with me on LinkedIn

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