Val has had an unbearable crush on Hugh for months, and his friends are urging him to go for it. The problem? Val has no romantic experience. Zip, zero, nada. And Hugh is about to leave for a summer-long trip to Europe.
Enter Stef. Val's more experienced best friend volunteers to teach Val all about how to date in order to boost Val's confidence so that he can ask out Hugh when Hugh returns. Val thinks the idea is silly, but as Stef cooks up pretend dates to museums and baseball games and the sorts of things Hugh loves to do, Val does start to feel more comfortable in romantic settings. And it just so happens that he has tickets to a splashy movie premiere the week after Hugh returns, and it's the perfect occasion for a first date.
The problem for Stef is that all this fake romance is making him realize he has real romantic feelings for Val. Is he setting himself up for heartbreak when Val inevitably walks off into the sunset with Hugh, or can he persuade Val to stay with him?