Jon Hamm has been with the same woman since the late 1990s. He’s not actively looking to bring home any ladies, but let’s be honest, if he put his mind to it, he could probably do some real damage to the dating pool. He’s famous, successful, extremely handsome and gifted in other physical areas. Unfortunately, back in the day, none of those qualities helped him during a 1996 appearance on The Big Date when he lost to a stuntman and had to cry in his beer alongside the other loser, a dude with blond tips.

That’s right. Let me just spell this out in graphic detail. Jon Hamm, the guy on Mad Man who everyone in the world loves, showed up as a 25-year-old on a dating game show on USA Network, and the woman who had the chance to pick him passed, despite the fact that he offered to give her a foot massage after their date.

No doubt Hamm is probably a little embarrassed that this tape came to light thanks to Lighthearted Entertainment, but there’s no way he’s as embarrassed as this poor woman who decided to go with someone else. No doubt she’s kicking herself every day because even if the relationship would have failed, at least she could have spent the rest of her life telling her friends how Don Draper tried to wine and dine her.

Mad Man may not go on for too many more years, but Hamm’s career is generating more and more momentum. His new drama Million Dollar Arm is getting crazy hype, and his upcoming schedule is booked solid.

I think I speak for everyone when I say, thank God this devastating game show loss didn’t ruin his confidence. And also, thank God that he went away from that hair style. Ouch.

You can watch the entire episode below...

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