Some more/my ideas:
Constantinos: is a single writer, who pumps out bestsellers ala Bret Easton Ellis and Chuck Paluhniak- nihilistic stuff about the crappier side of humanity, with bittersweet irony and dark humour throughout. He lives in New York City in a crappy apartment that reminds him of the dorms at Bullworth, and still harbours feelings for Pinky.
Chrissie went on to do either fashion design or PR at uni, and has a fantastic job where she gossips about her colleagues, flirts with lots of men, and gets accused of hitting on people's significant others. She mightn't know pi to the third digit, but she can tell you exactly who designed your outfit, the name and phone number of the cute waiter serving you, and all about her boss' mistress and marital problems.
Trent went to Hollywood, and has a main part in a B-grade sci-fi series which is on late at night. His frantic lifestyle is catching up with him, he's not ageing well, and he still breaks out every now and then. He's due to appear on a Pro-Activ commercial, and as for his sexuality? He's happy for sex, whereever he gets it. He has a fanbase on the internet, though, and plenty of sci-fi fangirls/bois would happily shag him. He had a crystal meth problem and has been in and out of rehab, and the papers will every now and then run a report on his sexuality when it's a slow news day.