If you thought Kesha trying to hug a resistant Jerry Seinfeld on the red carpet was painfully awkward, wait until you hear about Judd Apatow getting pied by Paul McCartney.
The comedian and film director was appearing on Conan as he revealed that the Beatle used to enjoy his stand-up routines, telling host Conan O'Brien: "Paul McCartney kept coming in to watch the show - he loves comedy.
"He was always hilarious, and I would say 'hello' to him afterwards nervously. After a couple of times I thought, maybe I could ask him out to lunch.
"Maybe he's like the lonely cheerleader nobody asks out to lunch. Maybe he would like to hangout with me.
"So I had a piece of paper and a pen and I was like, 'hey, we should go out to lunch, listen to music, watch movies, we know each other a bit', and gave it to him like, 'how do I reach you?'
"And he goes like this [raises arms up in the air]. He was very nice, but instinctively said 'no'."
Luckily, a friend of Apatow's was there to capture the mortifying moment on camera because, what are mates for after all?
"But the next day, my friend was like, 'I was taking photos of you talking to Paul McCartney, and I found a photo of you', and he found a photo of that moment!'" the Hollywood producer laughed.
We feel your pain, Judd.