Being Funny in Conversation
Build up a repertoire of funny stories. While you don’t want your hilarious anecdotes to feel too staged, it’s a good idea to have a stock collection of amusing stories that you can reference in a pinch.
Stick with general topics that are light and fun and try to avoid stories that are gross or intimate unless you know the girl well. Remember -- just because your friends think it’s hilarious doesn’t mean she will!
Think about some amusing stuff that’s happened to you in the past, like the time you wore your shirt inside out for school pictures.
If you have a pet, you’ve probably got some hilarious pet stories to share!
To keep things fresh, frequent a few funny websites like The Onion and draw from those when you need inspiration.
Memorize some quality one-liners.
One-liners are not the tools to reach for when you want to show off your sharp wit, but they can be great when you want to be silly. The cornier, the better! You can make them about her or go with something more general. Avoid awkward one-liners that are sexual in nature though. Contrary to popular belief, girls don’t find those very funny -- you might even make her uncomfortable. A few examples of fun one-liners you can try:
“Did you tie my shoelaces together? Because you got me trippin’ over you, girl!”
“You have something beautiful on your face. Oh wait, that’s just you.”
“A computer once beat me at chess, but it was no match for me at kick boxing!”
Create your own style of humor
By playing to your strengths. Think about stuff you do or say that cracks up your friends on a regular basis, especially your female friends. If you’re great at physical humor, go with that. If you're a master of mimicry and impersonations, give those a try. If sassy comebacks are your thing, try a few of those in her presence. Just make sure they’re lighthearted and not malicious![3]
If you aren't sure what your strengths are, ask your friends.
Learn to laugh at yourself.
Don’t go off the deep end with self-deprecation, but targeting some silly things about yourself may crack her up. Draw from your personal experiences or learn to poke fun at yourself in the moment. For example, if you trip over something when you’re walking with her, you could say, “Well, there goes my dream of becoming a runway model!” This lightens the mood and also shows her that you’re laidback and comfortable with yourself.
Try not to rely on this tactic too heavily, since it can get awkward or just plain unfunny after a while. However, an occasional, well-placed joke at your own expense can be priceless.
Expect your humor to fall flat on occasion. In these cases, use the bad joke to make another and get the conversation going again.
Make funny comments based on past conversations or situations with her
This can be something as simple as, “Remember that time in history class when…” and then filling in the blank with a good anecdote. Or try to make a funny comment based on something she’s told you before – not only will she laugh, but she’ll probably be flattered that you remembered that detail.[5]
For example, if she told you she loves fashion, ask for her professional fashion advice and describe a terrible or ridiculous outfit you’re planning to wear to an upcoming event
