Ted sees a beautiful woman sitting alone at the bar reading a book. He and Barney argue on who gets the privilege of approaching her. After Ted wins the battle, he may change his mind as he soon finds out that she is a friend of an old girlfriend, Cindy, with who their relationship ended very badly. But Ted also remembers that Cindy's roommate - who Ted only saw the back of - could actually be Ted's soul mate. Will Ted risk approaching this woman while receiving the wrath of Cindy on the chance that that woman is Cindy's roommate? Meanwhile, Robin has had a difficult summer trying to get over Don, and the way she looks shows it. And Lily and Marshall have scheduled tonight as the first night they will try to conceive a child. Marshall has even saved himself for two weeks in preparation. But someone may get between Marshall and Lily getting together this evening: Marvin Sr., who is a little too involved in Marshall's life for Lily's liking.