Season 4, Episode 15
Despite Eric's misgivings, Robbie gets Annie's blessing to plan a Valentine's Day road trip for himself and Mary; Matt starts hanging out with Heather while avoiding Shana's phone calls, which worries Shana when Mary innocently spills the beans about Heather's return. Meanwhile, Simon covers up evidence of an intense make-out session with his girlfriend. Robbie: Adam LaVorgna. Mary: Jessica Biel. Simon: David Gallagher. Annie: Catherine Hicks.
Original Air Date: Feb 14, 2000
Maureen Flannigan: Shana