That's when Jon, now 43, was a 25-year-old contestant on The Big Date, where he competed against a stuntman and finance student with frosted tips for a date with Mary Carter, a 25-year-old animation student with "a foot fetish."
The other two gentlemen tried to woo Mary over first before Jon, whose job was listed as "waiter" rather than "aspiring actor," had a chance to (try to) work his charm by detailing his plans for a romantic date.
"Well, [we'd] start off with some fabulous food," said the semi-awkward but completely endearing pre-fame star, "a little fabulous conversation, end it with a fabulous foot massage for an evening of total fabulosity."
Um, adorable. Somehow, though, Mary picked the stuntman, though, leaving Jon for the taking when Shonia got her chance to choose a date. Then—and, yes, this is crazy—Shonia also skipped over Jon, opting to stick with the peroxide-friendly financier-in-the-making. In the end, Jon, having failed to score a date, went home alone.
Let this be a lesson, ladies: If you can just look past the middle part, gum-smacking and awkward usage of "fabulous," you might be able to snatch up a Jon Hamm before the other gals catch on!