The Baxter

In this romantic comedy, a man with a reputation for being a "Baxter" - the nice guy who always loses the girl to the leading man - tries to change his fate by standing up for himself and taking risks. Elliot Sherman is a mild-mannered tax accountant who has been left at the altar three times by his girlfriends. As he prepares to marry his current girlfriend, Caroline Swann, he discovers that her high school sweetheart has returned to town and fears that he will lose her again. With the help of his quirky temporary secretary Cecil and her unconventional advice, Elliot tries to break out of his "Baxter" role and win Caroline's heart for good. But things get complicated when Cecil develops feelings for Elliot herself, and he must choose between his desire for Caroline and his growing connection with Cecil. Will Elliot be able to overcome his "Baxter" status and find true love?

You can stream The Baxter on: Paramount+ Amazon Prime ⎥ Paramount+ Apple TV

Some movies that have similar genres and were produced around the same time as The Baxter include But I'm a Cheerleader, Eagle vs Shark, Yes Man, Serendipity, Killers, No Reservations.