Conan Awkwardly Hits on Kate Upton While Playing Video Games

Kate Upton joined Conan O’Brien for “Clueless Gamer,” where she thought she was just going to play a video game with her friend Conan — and then realized that he wanted to be more than just friends.

Conan described Upton as a “friend, partner — some would say soulmate.” He then sat her down at a romantic candlelit dinner that happened to be set up near his gaming console. When Antonio the violinist came out to serenade them, it started to get awkward.

Conan tried a variety of ways to win Upton’s affection, including asking her whether she noticed his cologne and suggesting that they play a game using one controller. “You can take your other hand and put it on top of my hand if you want to, ” he said.

When they won the game with the four-hands-one-controller approach Conan said, “When I suggested we work together, our bodies touching, it felt like we became one person.” Kate said, “Yeah, I was able to help you experience winning.”

In the end, Conan realized he and Kate weren’t soulmates, so he let her know there were no hard feelings by bringing out Antonio the violinist one more time.

In “Clueless Gamer,” Conan reviews video games with celebrity guests. In this case, he was checking out Cuphead for XBox, which will be available September 29. The game, inspired by 1930s cartoons, features cooperative play.

Conan airs weeknights at 11 p.m. on TBS. 

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