Kelly Taylor (Jennie Garth) on Beverly Hills 90210
When midwestern sweetheart Brenda (Shannen Doherty) moved to Beverly Hills, pretty and popular Kelly (Jennie Garth) quickly befriended her. The besties shared many things, including a huge crush on bad boy Dylan (Luke Perry), who Brenda later started dating. Then Brenda went away to Europe for the summer, and Dylan and Kelly promptly started hooking up. Can you say awkward?