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20 Awkward Questions To Ask A Girl

By on December 23, 2014

Sometimes you just really need to ask those embarrassing awkward questions, right? These awkward questions not only help you learn a lot about the people that you are potentially looking to date, but if you pop them in conversation at just the right time, you shouldn’t be met by too much of a surprised answer! 😉

1 – What is your bra size?

Awkward, yes. Sensible, yes. For a start, you know what size lingerie to buy her later! Most girls probably won’t tell you but it’s got to be worth a try! 😉

2 – What’s the most embarrassing / awkward moment you’ve ever had?

She’s again probably not going to tell you but if she does, there’s a good chance it won’t be all that bad anyway. Girls get really embarrassed by stupid little things!

3 – How many guys have you dated?

It’s not quite as crass as ‘how many guys have you slept with?’ but still gives you a good idea of whether you’re one of a long line.


4 – Why are you single right now?

You’re going to need to know if she’s just been through a nasty breakup. Firstly there’s the crying. Secondly she might go back to him. Thirdly she might just be crazy – that’s why she’s single.

5 – Have you ever experimented with someone of the same sex?

Just for interest really – there is no other reason to ask that question!

6 – Do you go out partying a lot?

You’re not asking if she’s an alcoholic, you’re asking if she’s going to be drunk-calling at 3am most mornings, or leaving the club with a different guy every night. If she’s out to protect her heart, you gotta be out to protect yours as well. Of course, she may just offer to go out a little less if she knows that her relationship with you is on the line!

7 – What’s your favourite kind of underwear?

Does she like french fancy pants, or a simple little g-string? Again, there’s no real reason for knowing this apart from pure intrigue, right?

8 – How much do you earn?

Well, the money thing is something that has the potential to make or break a relationship so it’s just plain and simple common sense to get this out of the way nice and early… Isn’t it?

9 – Does size really matter?

Always an interesting topic of conversation! 😉

10 – Have you ever regretted a sexual / romantic moment?

Perhaps you took someone home you shouldn’t have, or kissed someone you had positively zero interest in?

11 – What do you class as cheating?

Some people don’t think kissing is cheating. Some people think that talking naughty is fine as long as you don’t do anything naughty. It’s always good to set these boundaries early. After all, how happy would you be if you girlfriend was going around kissing random guys every weekend she got drunk?

12 – Could you ever forgive a cheat?

Take this question as you will…

13 – Are you a virgin?

This goes without saying, right?

14 – How long do you think you should wait before you get married to someone?

You don’t want a crazy girl that thinks she should have a ring on her finger within six to eight months, do you?

15 – How long does it take you to get ready in the morning?

You don’t want to date that girl that makes you wait three hours before you can actually see her in the morning, do you?

16 – Have you ever dated any of your friends?

You’re going to need to know which ones to keep a special eye on, and also make sure that no one gets close to stealing your girl. Those pesky friends – they have a habit of jumping out of the friend zone!

17 – Have you ever faked it?

Now ask her how good an actress she is!

18 – Do you think you could ever be in an open relationship?

What would the rules be for that open relationship?

19 – If you were given three wishes from a genie, what would you wish for?

It’s always a tough answer but you may be surprised by the three that she comes up with. We feel that you can tell a lot from how a person answers this questions!

20 – Do you have any fantasies?

Come on – you all want to ask but generally, you don’t have the guts to, right? We all want to know what our partners fantasise about. After all, don’t we all want to be the one that makes all their dreams come true? 😉