Blind Item Guessing Game: Back Door Play

Ben Widdicombe tosses us an extraordinarily puzzling blind item today:

Which Middle-American pop star, who really should have learned to stay off the Internet, has been chatting online again? Apparently his ultimate romantic ambition is a simultaneous date with an entire NBA team (except he didn't use quite those words).
We have noooo idea who you're talking about, Ben, and neither does Kelly Ripa. Psych, it's Gay Gay Gay Gay Gay Aiken. Gayken. BOTH HIS FIRST AND LAST NAMES RHYME WITH GAY. So what's the real question here? Well, we think it's this one:

Don't Shoot The Messenger [Gatecrasher, last item]
Earlier: Gawker's Coverage of Clay Aiken