1 Would you describe yourself as naughty or nice?
This one is bound to get her thinking and won’t really press her to feel the humor until you insist on her justifying the answer. Then the giggles will make a sudden and welcome appearance.
2 What would you do if you could be invisible for one day?
You can imagine some of the answers you might get to this question—nearly all of them hilarious. A funny question with definite ROFL potential.
3 What is your most embarrassing sexual moment?
Embarrassment is nearly always funny, even when it’s your own, as long as told in the right environment. Then it just becomes hilarious and something to be shared and enjoyed.
4 What’s the funniest thing that’s ever happened to you?
The clue’s in the question. If it’s the funniest thing she’s ever experienced, then it obviously has the potential to re-amuse at will. And you’ll be right there to share the frivolity with her.
5 What’s the weirdest nickname you’ve ever had?
You have to be in a position of trust to ask this one, and if you are, the embarrassment factor can deliver very funny results.
6 What’s the weirdest crush you’ve ever had?
Everyone has a funny story about some former puppy-dog crush, and an embarrassment reciprocated of this kind can lead to laughter all around.
7 Who would you do between…?
A choice question. Choose three of the most objectionable individuals you can imagine and then ask: if they had to have sex with one of them, who it would be? Ask them to justify their answers to add to the laughter.
8 What are the best and worst things about being a woman?
Expect some flak for this one, being a male of the species, but that’s half the fun. Let her unload on you and take it on the chin, showing her that you are a real man who can enjoy a laugh at your own expense.
9 If I caught you masturbating would you carry on, or stop and pretend you weren’t?
An extremely embarrassing question leading to hilarious answers and a lot of fun all around. Quite saucy too.
10 What’s your favorite joke?
Again, the clue’s in the question. It’s her favorite joke, so it is bound to get her laughing. And even if it’s terrible, it can become a source of amusement in itself.