Monday in New York is also a whirlwind of sight-seeing activities, which include the World Trade center site, MoMA, the Met, and a baseball game. Don finds the statistics of baseball fascinating; through that shared interest he makes a new friend, Dave, at the baseball game.

Rosie says she enjoys watching Don “fit in,” performing stereotypical “man” behaviors like talking about baseball and drinking beer. Rosie finally confides in Don that what she refers to as being “fucked up” (209) by her father began when Phil, who she believed to be her father, sat her down at age 12 and told her that he wasn’t her biological father and that her mother had had an affair with another man. Since her mother had died two years before, this blow took away Rosie’s one remaining parent. As a consequence, Rosie doesn’t trust men or believe that they are who they say they are. She expects men to let her down or disappoint her.

Don doesn’t know what to think of all this, and Rosie complicates matters by kissing him on the cheek as they part that night. Talking to Claudia by Skype, Don realizes that Rosie chose their activities carefully, maximizing the potential for fun while managing to make things interesting for Don.