Alice is happily married to Sam. As part of a drunken prank egged on by her sister Felicity, Alice sends Sam an anonymous Valentine’s card to see how he reacts. Unfortunately for Alice, Sam hides the card all too well which infuriates her. Alice also receives an anonymous Valentine’s card but it’s from a secret admirer – Sam’s best friend Archie. Alice thinks Sam sent it. What starts off as a silly prank escalates to phone sex, a clandestine meeting and ultimately the revelation that Sam already has a mistress!
After miraculously remaining 29 years old for almost eight decades, Adaline Bowman (Blake Lively) has lived a solitary existence, never allowing herself to get close to anyone who might reveal her secret. But a chance encounter with charismatic philanthropist Ellis Jones (Michiel Huisman) reignites her passion for life and romance. When a weekend with his parents (Harrison Ford and Kathy Baker) threatens to uncover the truth, Adaline makes a decision that will change her life forever.
Ike Graham, New York columnist, writes his text always at the last minute. This time, a drunken man in his favorite bar tells Ike about Maggie Carpenter, a woman who always flees from her grooms in the last possible moment. Ike, who does not have the best opinion about females anyway, writes an offensive column without researching the subject thoroughly. The next day, Ike gets fired by his publisher (and former wife), because he went too far and faked the facts, which real journalists don’t do. Ike’s only way back into the business now is to do a fact-based report on Maggie and her upcoming fourth wedding attempt, which Ike predicts to fail again. So, as he circles her like a vulture his prey-to-be, Maggie’s opinion of Ike sinks below zero. Not only is Ike waiting for her to fail again but the whole town is poking fun at Maggie about her mistakes. But that is a point which Ike doesn’t like.