Smitten with a woman he meets at the wedding, Ted decides to play it cool for a change and his all night romantic adventure with her doesn't even lead to a kiss or a phone number.

When a tape from Barney's ex-girlfriend is viewed by the gang, everyone must share their most embarrassing moment in order to get the full story from Barney on how she broke his heart and how their breakup changed him into the suit wearing bachelor he is today.