Mandy Ellis is an idealistic romantic who has resolved to improve her dating life and career in 1996. Her luck starts turning around when she meets Dan Zeller, an outdoorsy, athletic cyclist from Wyoming. He introduces Mandy to outdoor activities, and she introduces him to fried pies and other Southern dishes.
The romance heats up until reality sets in. Dan forgets her birthday, and his dot-com start-up begins to demand more of his time. Mandy creates a business plan for the dot-com, but Dan doesn’t seem to take it seriously. She wonders if their relationship is mostly based on physical attraction.
Mandy and Dan decide to temporarily break up so that they can reconsider their relationship.
During a business trip to Seattle, Mandy starts to notice her coworker Tyler. He had a longtime crush on her, but she thought of him as just a friend.
Mandy finds herself in a nested loop of love. Will she break out of the loop and find her way back to love?