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The date: September 11, 12:45am
The place: 117 MacDougal Street
Sighted: John Mayer at Comedy Cellar helping his buddy who was bombing.

The Jessica Simpson-John Mayer coupling seemed slightly off right out of the gate. The public, its level of confusion rivaled only by its apathy, wanted answers; sort of. What could they possibly talk about? Did this pairing with a woman who clearly wouldn't have looked twice at him in high school officially make him the musical Zach Braff? Or, did the fact that he dated Jennifer Love Hugetitts back when Braff was still just the awkward, big-lipped guy on that doctor show make Braff the acting John Mayer? Also, didn't one of Time Magazine's 100 most influential people in the world want someone who could appreciate all his witty, voice-of-a-generation blogging?

But. Wouldn't Jessica Simpson be more comfortable with someone more muscle-y who didn't make her stare at all those tiny words?

Only in the past week have the answers to some of these pressing questions become clear. John Mayer wants very badly to be funny, and though her boobs are obviously a nice bonus, the guy is just doing Jessica Simpson for the jokes. Let's look at the time line:

June '06 - John Mayer bombs horribly at the Comedy Cellar with borderline racist material and vague, uninspired jokes about how sluts have "unlocked their masterlock for him".

August '06 - The John Mayer, Jessica Simpson rumors start. Both People and Us Weekly declare her madly in love. In response, John throws up a simple 'don't believe the hype' Public Enemy reference post on his blog and it's sort of funny.

November '06 - The two are back on and realizing perhaps that good comedy lies in the details: jokes about sluts are not that funny, jokes about a particular slut that everyone knows are funny. John returns to the Cellar with a victorious "not bad" set. Granted, the play-by-play we got from the cokehead who saw it leaves something to be desired, but common sense seems to indicate he threw a few Jessica Simpson jokes in there.

April '07 - SNL sets its mediocre comedic sights on the couple and you can almost see John watching at home, head raised and fists clenched as the tears of joy stream down his face; "Oh god, they're laughing. They're finally laughing!" he cries. In our mind.

And now after a break-up at the beginning of the summer and some unfunny Cameron Diaz sex, Jessica is spotted sneaking out of his apartment and the guy is now a comedy superman. The only question is; how many times can he do that dead-on impression of Joe Simpson teaching him to be good to his daughter before the hunting for new material must start?

Previously: Tears Of A Butterscotch Clown