When the only other virgin in her group of friends loses it at Keely's own eighteenth birthday party, she's inspired to take things into her own hands. She wants to have that experience too (well, not exactly like that--but with someone she trusts and actually likes), so she's going to need to find the guy, and fast. Problem is, she's known all the boys in her small high school forever, and it's kinda hard to be into a guy when you watched him eat crayons in kindergarten. So she can't believe her luck when she meets a ridiculously hot new guy named Dean. Not only does he look like he's fallen out of a classic movie poster, but he drives a motorcycle, flirts with ease, and might actually be into her. But Dean's already in college, and Keely is convinced he'll drop her if he finds out how inexperienced she is. That's when she talks herself into a new plan: her lifelong best friend, Andrew, would never hurt or betray her, and he's clearly been with enough girls that he can show her the ropes before she goes all the way with Dean. Of course, the plan only works if Andrew and Keely stay friends--just friends--so things are about to get complicated.