LOST

When they grew up, there was a bit of a schism in the old friend group between the kids who pivoted to other interests and the kids who became a more formal theater troupe. Winslow's best friend Sundew ended up taking off with the troupe and moving to California to try and get into Hollywood. He was going to meet her in LA coming back from Sydney and tour up the coast with everyone to meet his Portland friends Will and Serenity and throw a big reunion show. (Which still actually happened, it just became the Winslow Evans Memorial Festival, sponsored by Green Bean's Green Earth Coffee)

These are Winslow's primary friends, he has a much larger social circle of pleasant acquaintances but they tend to orbit around these guys.

Tamara and Winslow as kids

The sibs + glethan besties. Glenn has like light brown hair thats why some picrews I make it dirty blonde if theres only a dark brown. His mom is actually like yellow blonde though and they don't look the same.