First and foremost, LOL @ the title of this video being "Say You Will Freestyle." Usually a freestyle involves rapping or poetizing of some sort, rather than sing-speak-autotuning the fairly literal details of a failed late-night hookup. But credit to Kanye's unconventional genius (and the awesome piano part to "Say You Will") that he actually makes something highly listenable out of the venture, and you'll be hanging on his every word as his story gets later and later at night and the stakes get higher and higher. Will Kanye get himself laid? Will he get a taste of "type of pussy you risk your life for...the type of pussy you leave your wife for"? (Spoiler: No. But you should watch/listen anyway.)
At the very least, we get an all-time great and all-time definitive Kanye moment as he ponders about halfway through: "Who you gonna listen to, your ego or your dick? / Ohhhhhh, dick wins." Usually does, 'Ye.