Dawson takes Joey up on her invitation for a weekend in Boston, but the two have reservations once there. Meanwhile, Jack is surprised when his boyfriend Tobey shows up unexpectedly forcing Jack to choose between fraternity hell week and spending time with Tobey.

Jen helps Dawson go to the shrink he ran away from last week. Dawson still thinks that the whole idea of sharing his thoughts with a complete stranger is weird, but he is surprised with how much he learns from it. Back home, he has to handle the problem with his father will, which does not include Lily. Meanwhile, Joey is working on a project about old love letters written by an obscure writer, and with the help of Audrey's audition tape for "The Real World: Ibiza", she manages to catch something no one of the fellow students caught. Pacey confronts Karen about the risks she is taking for having an affair with Danny, and Karen is hurt when Danny's wife shows up at a dinner party and he blows her off completely.