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20 Awkward Questions Guys Ask Girls



I’m never quite sure whether to tear my hair out, punch the guy or just politely brush it away when I hear some of these. I’m sure you’ve all run into at least one guy who doesn’t hesitate to ask awkward questions to a girl. Maybe we should hold up a sign saying “Hey that’s an awkward question”. Do you think that would shut them up? Probably not. Here’s a list of some of the most awkward questions to ask a girl.

Boys, pay attention and despite your first instinct, do not ask the girls you actually like these questions!

1. Is your sister/friend single? – Awkward especially when you’re the one eyeing him
2. Am I your type?
3. Are those real? – Drunken guys really come up with the most awkward questions to ask a girl.
4. What is the most embarrassing thing that has ever happened to you?
5. Why are you single?

6. Have you ever done drugs?
7. How much does your job pay? – Boys, this is definitely an awkward question to ask a girl, especially if you’ve just met.
8. Tell me something you haven’t told anyone before/What’s your deepest darkest secret? – What makes you think I want to tell you?
9. How many partners have you been with?

10. Can I kiss you? – This is such an awkward question to ask a girl. A good response would be “Only if I can punch you”.
11. Is it okay if I sleep over?
12. Have you tried peeing standing up?
13. Ever been with a woman?

14. Do you like that? or other such questions in #bed. There is no right way to answer that and that’s what makes it an awkward question to ask a girl.
15. Why did your ex and you part ways?

16. How come you didn’t return my call? Don’t make it embarrassing for yourself and for her by asking this awkward question. Obviously, she saw your call and chose not to return it.
17. Does size really matter? – especially when you know he’s not as ahem gifted.
18. Was s*x better with your ex than with me?

19. Anything to do with STD’s- Important no doubt but also an awkward question to ask a girl.
2o. Have you put on some weight? – This is possibly the most awkward question to ask a girl. Boys, if you value your lives, find a nicer way of telling her she’s put on weight.

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