Jon reminisces about the time he asked a young Jennifer Aniston on a date. Ah… New York in the mid 90s… An Italian restaurant on 10th street… Jon waited for her on the stoop…

This is kind of a romantic story. But I think Jon is better off that they never hit it off. Would we ever have taken him seriously if he was Mr. Rachel Gellar?

Video after the jump…

The Daily Show With Jon Stewart Mon – Thurs 11p / 10c
Jennifer Aniston
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