A Ring by Spring

The film opens with Caryn Briggs expressing her disdain for the romantic tragedy of 'Romeo and Juliet,' arguing that Juliet threw her life away for a guy she just met. At a charity fundraiser, Caryn and her friends visit a fortune teller named Madame Rue. While her friends receive positive or cryptic messages, Caryn is given a chilling ultimatum: she will receive a ring by spring or she will never marry. Shortly after, Caryn expects a proposal from her boyfriend Bryce at a fancy restaurant, but he instead breaks up with her, claiming she isn't 'marriage material' because she lacks a desire for family and commitment. Distraught by the prophecy and the breakup, Caryn takes a consulting job for Tom Halsey, the CEO of a successful but disorganized college surplus company. To understand her 'failure' at marriage, Caryn decides to track down her ex-boyfriends—Rory, Dave, and Josh—to ask why they moved on. She discovers a pattern: she is 'low maintenance' and independent to the point of making her partners feel unneeded. Meanwhile, she develops a playful, geeky rapport with Tom, bonding over 'Office Space' quotes and bowling. Desperate to beat the spring deadline, Caryn reconciles with Bryce, trying to force herself into the role of a traditional fiancée. However, Tom challenges her, asking if Bryce truly 'gets' her the way his late Uncle Harry 'got' his wife Cora. Realizing she is settling for a man who wants to change her, Caryn breaks up with Bryce for good, accepting the possibility of being alone. On the first day of spring, she encounters Madame Rue again, who offers a refund because the prophecy seemingly failed. Caryn realizes the prophecy was a wake-up call to be herself. She heads to the bowling alley to see Tom, who gives her a prize from a 'Cracklin' Fun' snack box—a toy ring. This literal 'ring by spring' fulfills the prophecy in an unexpected way, and the two finally begin their romantic journey together.