All Grown Up! (2003)

S5E6 All Broke Up

Tommy's girlfriend, Rachel, is relocating, and he appears to be fine with it, though he can't quite figure out why. His friends, however, suspect he’s in denial about his feelings. Tommy attempts to carry on with his daily life, but their constant attempts to show sympathy only frustrate him. Dil suggests that Tommy play along with his friends' concerns to gain some peace. When Tommy ends up hooking up with another girl, the group surprises him with Rachel's unexpected arrival. Seeing him with someone else hits Rachel hard, prompting her to leave again, leaving Tommy genuinely heartbroken. Chuckie arrives at Tommy's house to console him.