A high school senior must choose between enrolling at the college of her dreams and remaining at home to take care of her bipolar mother.

Longtime friends Ronny and Nick are partners in an auto-design firm. They are hard at work on a presentation for a dream project that would really launch their company. Then Ronny spots Nick's wife out with another man, and in the process of investigating the possible affair, he learns that Nick has a few secrets of his own. As the presentation nears, Ronny agonizes over what might happen if the truth gets out.

What if pain was merely a set up for the ultimate surprise party? Genie Burns, owner of Surprise Enterprise, masterminds off the wall surprise parties in nobody would-suspect-it locations. Here she takes crazy risks but in her love life, she plays it safe. Her partner Steven, who hilariously calls her out on every issue she owns, is gay which makes him safe. Danny, her friend from college would be perfect for her but she keeps him in the friend zone. Along comes Jeff, everything she avoids, but his charm and depth draw her in. Is he the right one because he challenges her fears, or the wrong one because he implodes them?

On a flight home to Chicago for a family wedding, childhood friends Josh and Molly innocently agree to fake a wedding engagement to make Josh's dying father happy. Things quickly get out of hand with their two boisterous families, and a series of events causes them to pretend to be a couple and start planning a phony wedding. When the playacting begins to foster real feelings, the two must make some serious decisions: Split up and return to their lives in LA, or make a life as a couple back in Chicago?