Admitting you need advice to figure out what's cool is never easy, but when you're defending your love for Joey McIntyre by exclaiming "Well, you like Justin Timberlake", aren't you really just crying for help? To avoid mockery, avoid friends, and turn to Cherrypeel.
In the spirit of Digg/Reddit, Peel's a free music community letting members vote up or down on posted tracks from new and emerging artists, using a +1/-1 point ranking system that monitors the popularity of individual songs -- an optimistically democratic MO devoid of hanging chads and easily confused Boca Raton grandmas. Once registered, you're free to peruse, stream, and vote on songs using various filters (genre, new, popular, etc), browse others' playlists for inspiration, and become "friends" with members who share your new, rapidly improving taste, unlike old friends who know you as the guy who cried when Estefan jettisoned the Sound Machine. When you find artists/tracks you like, use "earmark" to bookmark them, or add them to your own playlist, so you can get back to hot jamz ranging from heavy-hearted indie like "The Gun In God's Hand" (Slowmotion Club) to catchy pop-ish "Chick Flick Tears" (Go Periscope) to guilty pleasures like Schrute's "Take Boba Fett Seriously" and Distortion Method's "I Wipe Myself" (their parents must be very proud).
Active users acquire "karma" points, and according to the site managers "The more karma you get, the cooler you are. Trust us". Trust you? You don't even offer tunes from 2001's Meet Joe Mac!