Apparently, a Hollywood airline booking agent has a great sense of humor. The agent booked Kim Kardashian’s new husband, NBA star Kris Humphries, and Kim’s ex-boyfriend, pseudo-singer Ray J, on the same commercial flight.

According to Gawker.com:

Kris Humphries reportedly wound up sitting next to his wife’s doggy-style sex tape partner Ray J in the first class cabin of a Delta airplane, and dealt with it in the saddest, most awkward way possible: He sat frozen in his seat “across the aisle” from Ray J “for a few minutes” (Did he stare blankly in stony-faced horror? Bow his head and sneak furtive side-eye glances at the man whose legacy he fears more than anyone else’s?) then switched seats and sat in “awkward silence” until Ray J walked up and congratulated him on the marriage, at which point “Kris acted like he didn’t recognize him.” Apparently “Ray J said, ‘Come on, you know who I am. I just wanted to say congratulations.’ Then Kris, realizing he was cornered, said, ‘Oh yeah, yeah, I’m sorry, I know who you are.'” And the size and shape of your penis, and what you look like orgasming all over my wife.

The word “awkward” gets tossed around a lot, as does the “most ______ ever” headline construction, but I suspect this was actually the most awkward moment of Kris Humphries life, if only because his life seems like it’s been kind of boring so far. I mean, relatively boring, for a filthy rich 26-year-old baller, at least. Source

By the way, a mystery buyer contacted Vivid entertainment recently to inquire about removing said sex tape from circulation. The buyer wants to purchase the sex tapes and all of the outtakes with Kim Kardashian in them. TMZ.com thinks the buyer is Kim herself.