Montana Moore, a flight attendant, is determined to find a man before her younger sister's wedding. Feeling the pressure from her mother and driven by her desire to avoid being the last unmarried woman in her family, she sets herself a 30-day deadline to get engaged. To accomplish this, Montana enlists the help of her fellow flight attendants, Gail and Sam, to track down and orchestrate encounters with her numerous ex-boyfriends who might be Mr. Right. This plan involves crisscrossing the country and arranging "chance" meetings with these past flames, hoping one of them will rekindle a romance.

As Montana reconnects with her exes, each encounter brings its own set of challenges and comedic mishaps. Despite the best-laid plans, she discovers that revisiting past relationships may not be the solution to her quest for true love. Throughout her journey, Montana learns more about herself, what she truly wants in a partner, and the importance of genuine connections. The story takes her on a whirlwind adventure filled with humor and heart, ultimately leading to unexpected revelations about love and relationships.