When Doogie decides to get his own place, he and his parents go look at some apartments but none of them is to his liking. But when he finds a loft, he feels this is it but his father refuses to support him if he decides to take it.
Doogie is planning his New Year's celebration. He comes home and finds a girl there. He learns that the man who rented him his place also rented it out to her. They try to live together but the girl is very fancy free which drives the uptight Doogie crazy.
Doogie learns that his former babysitter and crush, Rachel Wilson (Chelsea Noble) is in town. He hasn't seen her since he was 10 years old. Could his old fantasies finally come true? Vinnie attempts to get his movie script to a famous Hollywood actor, Nathan Gage (Jeff Yagher).
Doogie, feeling unsatisfied with his position in life, decides to take acting lessons. This develops into a real identity crisis, so Doogie decides to leave the hospital and travel the world to find himself.