So Little Time - Season 1 Episode 12 Rules of Engagement

When some seniors advise the girls to look into college entrance information early, Chloe and Riley discover that they're interested in different schools and decide to try a ""trial separation"" to see how it would be like living apart from one another. Larry winds up being the go between for the girls, helping them to decide what to wear after they come to school in the same outfit; unfortunately, he loses it after a long cram session that requires him to keep running back and forth from Jake's trailer and Macy's house to study with both girls. Macy and Jake, growing tired of finding other people to date, decide to start over and have ""first dates"" as if they never met before as a method of rekindling the sparks.