How to Be Funnier on Dates (Even if You’re Not Funny)

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be funnier on dates

In dating, it helps to have a good sense of humor. Siyan Li shares what makes people funnier on dates in this episode of Last First Date Radio.

My podcast guest, Siyan Li, is a passionate humor investigator. She has analyzed 600+ talk show videos (yes, she admits to having mild OCD tendencies) to uncover exact lines, formulas and actionable strategies for anyone to be funny and witty, fast. Her work has been featured on Science of People, Humor That Works and Medium publications, gathering more than 100K views.

Check out the show notes and listen to/download EP 368: How to Be Funnier on Dates (Even if You’re Not Funny) below.

How to Be Funnier on Dates (Even if You’re Not Funny)

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What got you started as a humor investigator?

I had spent a lot of time trying to figure out my life passion. Unconsciously, I was watching and analyzing talk shows for the past few years. I realized, maybe this is it. It’s meaningful to make people happier. Why not become a humor investigator?

Why is being funnier on dates so important?

The most important reason is to break the initial awkwardness. I recently came across a quote.

Humor does not rescue us from unhappiness but enables us to move back from it a little.

– Mason Cooley

Humor is also a shared world view. If we both find the same things funny, it’s helpful to connect us.

Can people learn to be funnier on dates even if they weren’t born funny?

I do believe that. If you ask comedians, a shocking number will agree as well. Many have cultivated their humor. They create a bunch of stuff they try on stage. They keep what’s funny. But, we’re not trying to become comedians. Just to make people around us happier.

What are some of ways for anyone to be funnier?

Call back: Throw a joke back into the conversation when it’s been previously told. (On the podcast, you’ll hear an example with Connie Britton and Ellen Degeneres.)

Misdirection: Set up an expectation for things to go one way, and then go another way. One way is to play with numbers, as in the example with Ellen and Amy Poehler. Or with Sophia Vergara talking about a party for her husband, Joe. (You’ll hear examples on the podcast.)

Using visuals: Show funny pictures and let those pictures do the work for you. It’s useful for public speaking. Graham Norton starts his show with funny pictures.

How can you put those methods into practice?

For callback, whenever your date makes a joke, remember it, and later in a conversation, you can try to throw it back into conversation. For misdirection humor, if you talk about a big number, add the word ‘only’ before it (example: we had a small party, only about 150 people), and if you’re talking about a small number, set it up as being huge.

You can get a copy of the slides and video clips Siyan used in the show here:

Email Siyan at:

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