Ever wondered why talk shows are so lively? If you are thinking “a sociable personality”, then you’re right.  Dating is more or less the same. No matter how good you are with meeting women, you will run out of things to talk about at some point. So what if there was a way to meld romance and humor into a healthy dose of thought-provoking questions? What if there was a way to keep the girls coming back for more?

No girl wants to be stuck with a “Wyd” or “How’s the weather” kind of guy. So having an inimitable set of backup questions in your colloquial arsenal will hurl your attractiveness and compel her to like you more.

Whether it’s a physical date or just a simple random chat, delivering a line that leaves her laughing her ass off all evening is not easy. Sure you could go for the clichéd jokes about how she fell from heaven, or you could go with the cheesy one-liners, you know, the “you are a thief, because you stole my heart” kind of thing. But they will probably just make you seem archaic and pathetic.

So let’s try something different. The best way to a woman’s heart is through her mind. First, you want to appeal to her sense of humor to make her feel comfortable around you. Then you want to slowly build up the conversation by reliving her past experiences and getting her to talk about herself. Asking provoking questions that put her in humorous hypothetical situations will keep her fully engaged and allow her to discover the humor herself. It’s also less egotistical and a good way to open her mind to more exciting things, like sex. At this point, you can get as flirty as you want. Believe me, she wants you to.

I have compiled a list of 40 funny and flirty questions to ask a girl you like on a date to initiate the ROFL effect. Go easy on them though; don’t ask one question after the other. This is a date, not a police investigation. Start off with the most obvious thing about her, and build up the compliments.

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Now, let’s get flirty…

1.       What is the one weird thing you like; your secret guilty pleasure?

2.       What is the silliest pickup line a guy has ever tried on you?

3.       Have you ever has a successful blind date?

4.       Would you rather be in love or have lots of money?

5.       Where are you most ticklish?

6.       What is your favorite fun thing to do with a guy?

7.       What is more romantic; a guy cooking for you or a guy dancing with you?

8.       If you were to ever see me naked, which part of my body would your eyes first wander off to?

9.       Would you describe yourself as naughty or nice?

10.   What is your wildest sexual fantasy that you want to try at least once in your lifetime?

11.   If we were trapped in an elevator for an hour, what do you think we’d do?

12.   What do you wear to bed, if anything?

13.   What would you say you are drawn more to in a man; Brains or looks?

14.   What do you think is the one thing all men should do when dating?

15.   Have you ever had an unexpected orgasm?

16.   Thongs or panties?

17.   If I had to do something naughty with you, what would you prefer the most out of me?

18.   Do massages make you wet?

19.   What is the first thing you would do if you woke up as a man one morning?

20.   Have you ever been in a catfight? You look like the kind of girl who likes to have her hair pulled 😉

21.   What is the funniest thing somebody has ever walked in on you doing?

22.   That dress looks gorgeous on you. Is this your favorite color? It sure complements your eyes…

23.   What’s the one stupid thing you’ve tried but will never try again?

24.   What would you do if you were invincible for one day?

25.   What is the worst thing about being a woman?

26.   Would you rather kiss an ugly guy or an ugly girl?

27.   Would you rather be beautiful and dumb or ugly and smart?

28.   If you had to change one thing about me, what would it be?

29.   Tell me something nobody else knows about you

30.   If you had to cuddle with an animal, which animal would it be?

31.   What is the ugliest thing you own?

32.   How seriously do you take horoscopes?

33.   Are you a morning person or a night person?

34.   What is the best excuse you ever made not to hang out with your boyfriend?

35.   Do you have any tattoos in any weird places?

36.   If you could ask me anything, what would it be?

37.   What is the first thing that comes to your mind when you see me?

38.   What makes you smile about us?

39.   Do you think you would know if I was feeling horny?

40.   Don’t you think it’s a crime for you to be so beautiful and single? Don’t you think we’d make cute babies together?

Okay, the last one sounds a little corky, but it’s a great way to finish strong – and it works, believe me.


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