If you want some awkward questions to ask a guy, choosing your questions will probably depend on why you want to ask. Are you asking just for fun? Do you want to embarrass him? Is this a flirty game? Obviously, some questions could be REALLY awkward, and others might be not so bad, so it is recommended that you choose your questions with caution, and *ALWAYS* consider possible repercussions.
That said, asking awkward questions can be great fun and makes for more interesting conversation than the usual “get to know one another” type questions, so we would definitely recommend a few rounds of “asking each other awkward questions” if you want to really get to know somebody better.
Down the page is some information to help you become a master! Lets call it a Master Class to know exactly what a man wants and have him wanting you as a result.
Awkward Questions To Ask A Guy
Choose 3 people who you would Kill, Marry, and have sex with.
Guys don’t often like being honest about their feelings, so two of those questions would be pretty awkward and you might find that you don’t get straight answers, or you get celebrities listed instead of people that you both know more closely.
Have you ever been in love?
Guys don’t like admitting things like this, but if the guy is close to you he won’t want to seem like he has no feelings whatsoever, so he might stumble over this question wondering what his ideal answer should be. Sometimes guys forget that they should just give the most honest answer and instead try to guess what you will want to hear.
Do you think X is pretty?
Guys HATE this question. If “X” is your friend, what does he say? If he says NO he risks offending you for being mean about your friend, if he says YES he risks angering you for eyeing up your friends. This is perhaps the ultimate question for putting a guy on the spot, except for this next question.
Do I look Fat In This?
You would think that this is an easy question for a guy, the answer is of course NO NO NO, but for the guy, they don’t know how to say it and sound sincere, even if you really do not look fat in said outfit, he will panic over the question.
Which of my friends would you like to kiss?
This will probably be more awkward if you are in a relationship with the guy you are asking, but can still put him in a sweat if you are good friends.
Is my mom hot or ugly?
Assuming he has seen your mom.
Do you know any good porn sites?
Guys never know whether they should admit to watching porn or not, so this is quite a good question to ask them. Don’t feel offended if you get linked to some horse-porn though, he might be just calling your bluff…..or not.
Some Sexual Awkward Questions To Ask A Guy
You might think asking “How big is your penis?” is going to be an awkward question, but a lot of guys are hoping you will ask them this question, it gives them free reign to ask you about your bra size, or ask you if you would like to come and measure it for yourself, or all sorts of things, so it is up to you if you would like to ask that one. A more awkward one might be:
Do you masturbate?
Or even better, assume that they do, and ask them:
How often do you masturbate?
If you want to take it even further, why not ask them:
What (or who) do you think about when you masturbate?
Depending on how good your relationship is with that particular guy, you may want to branch out and ask questions such as:
Do you think your mom is attractive/sexy/f*ckable? (Be careful not to go too far here!)
I think most guys wouldn’t even THINK about answering this question but if you really want to go there, it sure will be awkward.
Have you ever had a wet dream, what was it about?Not all guys have had these, it seems to just come down to luck I believe, but will certainly make for awkward conversation!
Do you think my twin sister is sexy?
Obviously you need to have a twin sister for this one.
Master Class in Communicating with Guys
As you master various questions including awkward questions to ask a guy, you will realise what you can do by communicating with guys, or maybe that one guy. Both verbal and non-verbal language is critical. Do you want to know exactly what a man wants when he says “talk dirty to me”? Or are you a “nice girl” and want to make a man addicted to you without even touching him?
To learn the language of desire, to master the art click here or on the image below to find out more.
More questions beyond the awkward questions to ask a guy
If you would like some additional questions, try these:
- 20 Questions To Ask a Guy
- Flirty Questions To Ask A Guy
- Questions To Ask Your Boyfriend
- 50 Random Questions To Ask a Guy
- Tips On Asking Questions To Guys
As always, if you have any suggestions for more questions or more categories, please feel free to contact us.
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