July 13, 2017 at 07:55 AM EDT


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Better luck next time, Conan O’Brien. The late-night host and charmer of Conan tried used the latest “Clueless Gamer” segment as an excuse to get closer to Kate Upton, resulting in perhaps the most awkward forced date — if you could even call it that.

O’Brien surprised the model with a romantic dinner for two, complete with champagne and a violinist, before playing the Xbox game Cuphead. “I decided to team up with someone who I consider a friend, a partner, someone would even say a soulmate,” he said, though the “soulmate” part threw her off.

The late-night host promised this wining-and-dining routine was something he threw for past guests of “Clueless Gamer,” including Tom Brady. “He hit me,” O’Brien joked.

When they finally got to Cuphead, inspired by 1930s cartoons, things got even more awkward as O’Brien tried to make his game character hug Upton’s. “There’s a lot happening right now, sort of like in the throws of passion when you just let yourself go. Whatever happens, happens,” he slipped in.

“Oh, baseballs are on here, just like my fiancé,” Upton reminded him. That’s right, what must Detroit Tigers pitcher Justin Verlander think of all this? O’Brien didn’t appreciate that harsh reality too much.

In the end, Upton was able to shrug off the advances and whoop her opponent. “I was able to help you experience winning,” she taunted.

Watch “Clueless Gamer” in the clip above.

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