He's Just Not That Into You
This 2009 romantic comedy isn't all that romantic, and barely even a comedy, but it's the perfect level of mush to make you watch over and over again. Three best friends try to moderate their relationships at different stages and all must come to learn that they're not the exception to the rule. Sometimes, he's just not that into you!
Just One of the Guys
The "undercover girl dressed up as a boy" trope is pretty problematic looking back, but if you can get past that, this is a gender comedy that will make you yell, cry, laugh, and wonder. A girl is told she can't make it in journalism at her local high school, so she disguises herself as one of the guys to get investigative.