This episode begins with Liz Lemon seeing a cute little boy and his baby sister. Jenna points out that Liz is getting baby-crazy while she is getting turned on by car accidents. Liz denies her baby-craziness as Jenna discovers a baby shoe in Liz's purse. Liz defends herself saying that it isn't stealing if it fell on the ground. Clearly, she has taken the baby's shoe.
While walking down the street, Liz pats a man's head thinking he is a little boy. The man, Stewart, turns around and asks if he touched his head. She responds by saying she likes his tie. He responds by saying he likes aggressive women with a nerdy vibe. He then asks her out to coffee to explore this possibility. She responds yes and nervously talks nonstop while they take a walk. He then asks her out to dinner this week and she agrees.
Jack hires a new nurse to take care of his impossible, unpleasant mother who is only tolerable when sleeping. Later, Jack and the nurse Elisa talk about love – his view is you come in alone and go out alone. She believes in love while his plan is to get old and die alone.
Meanwhile, Jack also helps Tracy and his wife Angie develop a "post-nup" and gets Jenna an audition to play Janis Joplin
As Liz and Stewart are walking, Liz tries to pick him up to keep him from touching fire. He asks if she thought he was a child when they first met. She admits to this and he admits that he lied about her show and that he had seen it and didn't like it. As he walks away, she almost yells out that he should be careful while crossing the street.
Back at Jack's, he and Elisa are getting along very well. She tells him his plans for the weekend – going to her niece's birthday party. That weekend, Jack shows up at Elisa's family event to thank her for all her help.
At the office, Liz calls Stewart and asks for another chance. She asks to meet at the bridge at such and such time if they agree to stay together (she references the Sex and the City movie).
When Liz asks for advice, Jack has changed – he believes in love. He says that people should be surrounded by people and babies – people should not be alone. He admits he loves his mother's nurse.
Liz goes to the bridge and mistakenly thinks a boy is Stewart. Stewart sees this and realizes this will never work.
In the end, Jack comes home to Elisa and they kiss.