20 years ago Jordan Sterling had the experience of his life when he and his college girlfriend, Jennifer, hitchhiked from Ohio to New York after graduation. It was the subject of his only novel. After his agent hands him a boring writing assignment, Jordan receives a surprise phone call from Jennifer inviting him to their 20th college reunion that weekend. Oh, and by the way, she's divorced. Despite his agent's deadline, Jordan books a last minute flight from New York to Columbus, Ohio to meet up with his college buddy, Dr. Jim and drive to the reunion. Unfortunately, Jordan misses his plane. On a whim, he follows a young couple onto a train bound for Philadelphia. The girl convinces Jordan to hitchhike to Ohio, leaving him with a gift of magic mushrooms. Jordan gets off the train in Trenton, New Jersey to hitchhike. There's just one problem. No one will give him a ride. After trekking all night, running from a state trooper, and getting hit in the head by a beer bottle, Jordan catches a ride to the Columbus hospital where Dr. Jim is finishing an overnight shift. They drive to the campus where they immediately encounter Jennifer. She is as stunning as she was 20 years ago. Shell-shocked, Jordan follows Dr. Jim to the beer tent. When it starts to rain, they dash to a party where Jordan again encounters Jennifer. Though totally exhausted and sleep deprived, Jordan abandons Dr. Jim to take a romantic walk with Jennifer. They end up ballroom dancing with a group of seniors celebrating their 50th reunion. However, when Jordan makes a move, Jennifer rejects him. In an effort to console Jordan, Dr. Jim suggests they eat the psychedelic mushrooms and just have a good time. Instead, Jordan gobbles up all the mushrooms himself and the two old friends have a huge falling out. Alone and tripping, Jordan is confronted by his own worst demon, a talking Jackalope, who persuades him to give Jennifer one more try. In a final twist, Jordan learns a powerful lesson about living in the past.