EntertainmentCelebritiesConan O'BrienKate Upton

Conan O'Brien Puts His Creep On For 'Clueless Gamer' With Kate Upton

He isn't much of a player.
Open Image Modal
By 

General Assignment Reporter, HuffPost

|

Conan O’Brien turned up the awkwardness Wednesday for a “Clueless Gamer” episode with model Kate Upton.

The host broke out the bubbly, some violin music and a desperate persona for the sketch.

They played the 1930s cartoon-inspired game “Cuphead,” if you must know, but the bit was all about O’Brien’s dorky efforts to win at romance with a beautiful woman, “or a friend who thinks you’re an asexual freak,” he said.

Upton, 25, was eventually forced to remind the 54-year-old O’Brien that she is engaged to Detroit Tigers pitcher Justin Verlander.

The wooing went as well as expected.

Watch the full segment above.

Our 2024 Coverage Needs You

As Americans head to the polls in 2024, the very future of our country is at stake. At HuffPost, we believe that a free press is critical to creating well-informed voters. That's why our journalism is free for everyone, even though other newsrooms retreat behind expensive paywalls.

Our journalists will continue to cover the twists and turns during this historic presidential election. With your help, we'll bring you hard-hitting investigations, well-researched analysis and timely takes you can't find elsewhere. Reporting in this current political climate is a responsibility we do not take lightly, and we thank you for your support.

to keep our news free for all.

Support HuffPost

Before You Go

Suggest a correction
|
Submit a tip