First of all, Jimmy Fallon*, you're flip cup skills, WOOF. I mean seriously? It takes a lot to distract me from a certified bombshell playing my favorite drinking game of all time while kicking a red dress's ass inside and out but watching Fallon 17-flip on cup 2 was borderline astonishing. Like he had to be letting her win right? Bro we get it, you've got a top 5 smoke on the planet on your show playing flip cup, you let her win, but don't embarrass yourself. Respect the game.
That said I've got a question for all the hardcore flip cuppers out there. And I guess this is directed more at the male demographic, but let's throw out a hypothetical scenario. You're playing flip cup with Kate Upton (for the ladies we'll say David Hasselhoff as a comparable). If you let her win, you get to take her out to a nice seafood dinner and call her again but you can never play a drinking game again. If you demolish her you lose out on a once in a lifetime opportunity but maintain your drinking game integrity. Now on the surface this seems like an easy answer, and truthfully for 29 year old Jon it's a lay up because I play drinking games now about as often as the Olympics come around. But for a younger Jon that would be a toss up. When I was in my prime I was running anchor on some of the best flip cup teams in Point. People respected you if you were a consistent one flipper. Guy's wanted you on their team and women wanted to pour your beer. I'd imagine it would be like being a prized football free agent except not at all. So I dunno, I guess it depends on the age of the person you're asking.
*Fallon is the absolute best in the game with Kimmel a close second. My only hope is they let him keep trending young when he hits the Tonight Show instead of neutering him like they did Conan. Granted I don't watch Fallon consistently because I've got a better chance of flapping my arms and flying than I do of staying up until 11:30 on a weeknight. Sometimes on Friday nights though I like to get really crazy and stay up for Thank You Notes. Maybe even the first guest if I'm really feeling wacky.