20 Awkward Questions that Guys ask Girls and How to Answer

By on October 7, 2013

Awkward is in the eye of the beholder…at least when it comes to guys and girls. To guys, a question along the lines of how long it takes to get ready isn’t that awkward and most will answer with “five minutes”. However, to a girl, some of these questions are very awkward for a variety of reasons. Be ready for some of these awkward questions with our clever answers!


What happened in your last relationship?

This is awkward because if you answer bashing them, it looks bad on you and the guy might think you will say the same about him someday.

Best answer; “We just weren’t meant for each other.”


How many guys have you been with?

The trouble with this question is that it is never asked out of curiosity.

Best answer, “Enough to know what I’m doing.”


What age do you hope to be married by?

Tell your real friends the truth, tell a guy a generalized answer.

Best answer, “Whenever the time is right. I’m in no hurry.”


Would you ever be a stay at home mom?

Some guys prefer their wives stay at home with the children, while some cannot fathom supporting a woman who is perfectly able to work.

Best answer, “That is something I will have to ponder when the time comes.”


When did you lose your virginity?

Along with the number of guys you have been with, this question is never asked out of innocent curiosity. It is a “feeler” question.

Best answer, “Last week.” Then laugh and change the subject.


Do you want kids?

Guys ask this to size you up. Unless you are in a serious relationship, there is no reason to answer this question right away.

Best answer, “Maybe someday.”


Do you believe in women’s rights?

Discussing this in a serious relationship is one thing. Talking about it in a new relationship or something that you hope develops into a serious relationship is risky.

Best answer, “I believe that everyone has the right to an opinion and I respect all views.”


 Have you been in a lot of relationships?

People who have been in a lot of relationships or very few send out the vibe that something is wrong with them.

Best answer, “It depends on your definition of “a lot”. I’ve been in some.”


Have you ever cheated?

This is an awkward question because if you answer yes, you are automatically assumed guilty of always doing it.

Best answer, “What I’ve done before doesn’t define who I am now.”


How much do you make?

While this should be one of those questions that everyone knows not to ask, sadly people still do ask it.

Best answer, “I make enough.”


What are your thoughts on *insert controversial topic*?

After being in a relationship awhile, this is a perfectly acceptable question. In the beginning, it is awkward.


Best answer, “I think that issue is up for debate. There are good points for both sides.”


How long does it take you to get ready?

Guys ask this question to try to see if you are high maintenance without actually asking you just that.

Best answer, “It depends on the situation.”


How much did that cost?

Guys size up women by how much they spend on certain things.

Best answer, “I got it on sale for a good price!”


Have you dated any of your friends?

If you remained close with any of your ex-boyfriends and your new guy asks, you have to be honest. If he finds out later, it will be a big deal that you lied. Tell the truth, but change the subject quickly.

Best answer, “Yes, but there was no spark or chemistry at all.”


Would you consider a threesome?

You should never say never because some day you might be interested in trying new things. However, starting off a relationship with a man thinking you want to do more than you do is never good.

Best answer, “I am open to consider different things with the right man.”


What do you consider cheating?           

First of all, you should be very careful with a guy who asks this question. He is trying to see what he can get away with in the relationship.

Best answer, “Any kind of betrayal, even just emotional.”


Have you ever been called crazy by an ex?

Considering this is always the go to word of ex-boyfriends, most of us have probably been called crazy.

Best answer, “I’m not really concerned with what people call me. I know who I am.”


Do you pleasure yourself?                      

This question is awkward no matter who asks it, but especially a guy. Truth is that very few people do not so the guy asking most likely knows the answer, he’s just being a dirt bag.

Best answer, “I get my needs satisfied.”


Do you fake orgasms?            

Even if you have even just once in your life, do not answer this question.

Best answer, “I don’t think I would need to with you.”


Does size really matter?

Yes. Yes it does. This question is awkward though because guys don’t want to hear that. Just lie and say no. No harm, no foul.

Best answer, “No.”


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