Katie grows concerned when Anna-Kat is invited to join Westport's elite scout troop, The Wildflower Girls. Meanwhile, Taylor learns her Carnegie Mellon interview is scheduled with famous alumnus and Broadway star Brecken Phillips ; and, Oliver befriends the school recluse, Trevor.

Against Greg's wishes, Katie sets out to play match maker for British Greg. Meanwhile, Oliver goes along with a rumor at school about his sexual identity to help a classmate feel accepted.