Conan O'Brien turned his Clueless Gamer segment with Kate Upton into a date.  He repeatedly hit on her while they played a game called "Cuphead."

Conan tried to wine and dine the bikini model, even pulling out a violinist.  It was all for not.

While he ended up, with Kate's help, winning on the video game, he struckout when it came to making a connection with her.