Wesley is struggling to find a job and a partner and desperately wants to settle down in life. She goes on a date with a man named Sean. However, Sean ends the date abruptly when she mentions marriage and kids too frequently. Immediately after that, she slips, falls down, and meets a charming man named Jared. Jared seems like the perfect guy and Wesley starts to hide her true self in order to make the relationship work.
After Jared and Wesley finally have sex, the former does not contact her for a few days. Upset, Wesley gets drunk with her two best friends and the trio write a long and insulting email to him. However, Jared calls Wes after that to inform her that he had gotten into a car accident in Mexico, without having checked the email. To save her relationship, Wesley decides to go to Jared’s hotel in Mexico, sneak into his room and delete the email. She takes her friends, Brooke and Kaylie along.
Coincidentally, Sean is at the same hotel. Wesley gets thrown out of the hotel due to a few mishaps. However, she tries to break in again (against her friends’ advice), gets caught, and is jailed. After her release, Sean comes to pick her up. Wesley decides to meet Jared at the Mexican airport and fly back with him. She plans on deleting the email on the flight. Sean agrees to drive her to the airport. On the way, Sean tells Wesley that she had been his first and only date after the death of his wife. He had ended the date because it had gotten too real too fast. The two bond over the drive.
On the plane, Wes tells Jared about the email and comes clean to him. However, Jared breaks up with her since she had been hiding her true self. After that, Wes ends up fighting with her friends since they feel neglected by her. Back home, Wes finds a job due to Sean’s recommendation. Then, she apologizes to her friends and they forgive her. Wesley goes to Sean, who is at the restaurant where they had gone on a date, to ask him out. Sean, however, is on a date with Ellen, yet he agrees to date Wesley and the two kiss on the street. Ellen walks past them, complaining to her mother about her terrible date.