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20 Cute Questions To Ask A Girl You Like

By on March 28, 2014

Got a new girl that you *kinda* like? Want to get to know her more but worried about your lack of conversation-starter-pieces? Maybe you’re not getting anywhere and seem to be losing her attention?

Conversations with a new girl you like can be stunted and impossible if you don’t have the confidence to go in there and win her. The good news is that there are ways that you can get to know her – it’s all about asking questions and listening to what she has to say in response. Do you think you can do that?

Let’s say that you are on one of your first couple of dates together. You want to take things into a flintier direction but you don’t know how… Why not try one of these great cute yet flirty questions to ask a girl you like and get her really interested:

1 – When you look at a guy, what’s the first thing you notice? Is it his eyes? Do you always check out his abs? Are you more interested in his hair? (Why not ask what was the first thing she noticed about you?)


2 – What’s your favorite scent on a man? Do you like the cologne I’m wearing? Are you an ‘an natural’ kinda girl?

3 – Have you ever been caught naked or doing something naughty you shouldn’t? 

4 – If you had to make out with one of your same-sex friends, who would it be and why? Could you ever see yourself dating one of your girlfriends? Could you ever date a girl full stop?

5 – Does size really matter? It’s cute, that’s for sure, but it lets her know that you have body hang-up’s too. Sometimes it’s nice for a girl to know that her guy sometimes gets a bit insecure.

6 – What gets you hotter? Talking about sex over the phone, or via text message? Come on – we all ‘sex chat’, don’t we? 😉

7 – Are you an ‘on top’ or ‘on the bottom’ kind of girl? Chances are she wont’ answer but it’s got to be worth a shot, right?

8 – If you could be invisible for the day, what would be the first thing you’d do? (Let’s hope it’s a flirty answer directed at you!)

9 – What’s the cutest outfit you’ve ever worn for Halloween? It’s about the right time of year. You could always replace Halloween with any fancy dress occasion!

10 – Have you ever had a crush on a fictional character? Is the delectable My. Grey from Fifty Shades of Grey? Perhaps it’s Heathcliff out of Wuthering Heights? Most girls crush on a fictional character at least once in their lifetime… I wonder what hers will be…?

So we’re halfway there – how have you gotten so far? Do you know what her perfect fictional man would be? Do you know what she likes? How much closer have you gotten into that cute, flirty side of her? Do you need further assistance?

Why not try one of these:

11 – What’s your fighting style? Are you an angry monkey? Do you prefer to think of yourself as a runner rather than a fighter? It’s always good to get an idea of how scrappy she is. Plus, you’re probably going to make her laugh and all girls love a guy that can make her laugh!

12 – Have you ever tried something ‘naughty’ and not enjoyed it? Perhaps she’s not a fan of something between the sheets – at least you’ll know right from the beginning (if she even answers the question at all), and you’ll be steering the conversation towards the top of sex… Do you see what we did that? 😉

13 – Do you like to think of yourself as a happy person? Most women are hormonal creatures but it’s always good to know if she thinks she’s a moody woman, or if she’s normally a happy little fairy.

14 – Do you fancy any of my friends? It’s cute but dangerous – what if she answers yes?? At least you’ll know…

15 – What are your views on make-up sex? We personally feel as if there is no fight that a good bout of makeup sex or just hardcore making out can fix. Does she feel the same?

16 – What’s the cutest “I Love You” you’ve ever had? Getting an idea for her idea of romance is a really good idea if you want to get into her good books. Whether she likes to admit it or not, all girls love a bit of romance!

17 – Do you believe in soul mates?

18 – What three words first come to your mind when you are asked to describe me…? Make them good words!

19 – When we live together (obviously you are joking!), do you want us to have a cat or a dog? What would we call our first pet?

20 – What’s your idea of a happy ever after?

As you can see, dropping a few non-naughty questions in there is the great way to steer the conversation away from sex – you want to be cute, not a pest!

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