This joke worked well because the main punchline wasn't about how Leo has young girlfriends. It was about how private he is about his personal life. You can see when the joke switches to that, that he gets much more into it.

omg Leo DiCaprio's reactions to all of Nikki Glaser's jokes about him at the Golden Globes LOL
"What a career you've had. The most impressive thing is that you've been able to accomplish all of this before your girlfriend turned 30."

Spencer Althouse

Twitter

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