"To Have and to Hold" centers on Alice who still can't believe her high school crush, the dashing, wealthy and successful Joe Chambers, would choose to marry her and willingly allows him to mold her into his ideal socialite wife. Despite Alice's best efforts to be the woman of Joe's dreams, he can't help but be unfaithful to her. When Joe's indiscretions impact his career, Alice's life is further turned upside down. Alice unexpectedly finds herself falling for her best friend's boyfriend and begins to wonder if her fairy tale ending could exist after all.

Faced with their biggest challenge yet, the gang sets out to honor a lost friend only to find themselves in the middle of where it all began – Spring Break – where they learn their old school ways of partying hardly compete with today's generation.