We all have our own ideas about how these characters ended up, so here is mine.
Lila Fowler: After college, Lila moved to Los Angeles to try to make it as a hand model. Snubbed by Ingenue magazine earlier in her life, she decided to go a different route. On one of her first go-sees, she met an older, wealthy production designer. In a whirlwind romance, they wre married a few months later. Lila now lives in Beverly Hills and is a socialite involved with a lot of philanthropic organizations. She doesn’t really know the causes, but she does love hosting the benefits at her villa. Next year, Lila will join the cast of the new season of “The Real Housewives of Beverly Hills.”
Enid Rollins: After college, Enid attended Stanford medical school to study pediatrics. She met her husband in medical school, and they both accepted residencies in a small farm town in Iowa. When they are done, they plan to enter the Doctors Without Borders program to provide medical services to orphans in Uganda. Enid is very excited that Elizabeth thinks that this is very noble of her. She and Liz Skype every week.
Ken Matthews: was drafted into the NFL, first draft pick after college. He enjoyed his time in the spotlight until that pesky DUI. His performance slowly declined and after a bad hit in a game, his blindness returned. Terry, his former high school sweetheart, suddenly reappeared in his life. They have been together ever since, and now Ken does a speaking circuit of local high schools. Terry is his tour manager and agent.
Bruce Patman: despite showing some hints at reforming after college, he was unable to find a job after college, even when throwing around his family name. Finally, he had to stoop to taking a pity job from George Fowler at his microchip processing plant. After being fired for sexual harassment of female employees, he started to spend most of his time at nightclubs in LA, drinking and staying out to all hours of the night, and throwing his money around at expensive restaurants. He has been rumored to be canoodling with many celebrities and C-list actresses. Right now he is trying to launch his own line of leather carseat covers.
Steven Wakefield: After several years of working in a law firm at Sweet Valley, he finally came out to his friends and family. He met his current partner, Aaron Dallas, at a drag show in another town. Aaron, who was also not out at the time, feared he would be recognized, so was at the club in drag. He was wearing a curly red wig and a lacey white shirt when he met Steven. They’ve been living together for two years. They are the co-chairs of the Sweet Valley Pride committee. Steven has supported Aaron through his counseling psychology grad program. This has been very helpful for Aaron, who has now been able to see that all his rage issues that he blamed on his parents’ divorce was really internal homophobia and jealousy towards Elizabeth; he was harboring a secret crush on his high school best friend, Jeffrey French.
After graduating college, Winston Eggbert moved to the Bay Area and helped found a start up company called jokebook, where users can create profiles and connect over their favorite punchlines. The company was bought by Facebook, and now Winston was able to quit working and pursue several of his dreams. When the competitive eating career did not pan out, Winston started writing stand-up and eventually was hired to write for the Jay Leno show.
More later. Also, thanks for the link, Gothamist.