The latest Clueless Gamer segment sees Conan O’Brien teaming up with Kate Upton for a game of Cuphead, but not before trying to win her heart, of course.
After trying to melt Kate Upton’s heart with a romantic dinner and some music, the two finally get to playing Cuphead. Conan has never really been good at video games and this is even more apparent when playing the hard as nails Cuphead. Kate seems to get the hang of it while Conan just continually keeps dying. This doesn’t stop him from awkwardly coming on to Kate, who casually dodges his advances. We don’t get to see much of Cuphead (which is a shame) but, after waiting so long for its release, seeing anything of the anticipated game is welcome.
The segment ends with Conan’s broken heart as Kate seemed unfazed by his charms.