Before Jon Hamm was playing winning female viewers’ hearts as Don Draper on “Mad Men,” he had a tougher time with the ladies as a contestant on a dating game show.

TMZ posted the clip of Hamm in 1996 on a show called “The Big Date.” On the show, he competed against two other men to win a date with a female contestant named Mary. Even though Hamm promised her a fabulous night, Mary picked another guy over Hamm. Big mistake, Mary.

The show was hosted by Mark L. Wahlberg, who now hosts “Antiques Roadshow.”