It's rude to string people along.
Bob is willing to do anything for Jen, and Jen knows that Bob is interested in her.
Jen has to decide whether to tell Bob that she's not interested.
Jen tells Bob that she doesn't want to date him and that she just wants to be friends.
Jen continues to string Bob along so that he can keep buying stuff for her.
Bob finally realizes that he doesn't have a chance, so he can move on.
Bob wastes a lot of time thinking about Jen, and he never gets to date her.