Thirty-five-year-old Tripp still lives with his parents Al and Sue in Baltimore. His best friends Demo and Ace also still live in their parents’ homes and seem proud of it. Tripp has many casual girlfriends. When he is tired of them, he invites them to “his place”—and when they realize he still lives at home, they promptly dump him.
Al and Sue are fascinated when their friends, whose adult son recently left home, reveal they hired an expert to get him to move out. The expert is Paula, who believes that men continue to live at home because they have low self-esteem. Her approach is to establish a relationship with the man to build his confidence, then transfer his attachment from his parents to her.
However, Tripp does not fit the profiles of Paula’s previous clients, as he has normal social skills, good self-esteem, and a good job he enjoys. After some time dating, when he sees she might be getting too attached, he stages an awkward encounter with his parents. Paula thwarts Tripp’s usual M.O. attempt to dump her by having sex with him, while developing real feelings.
Both Paula and Tripp find themselves in unfamiliar waters, so confide in their friends. Paula’s roommate Kit, exasperated by her vocation, theorises that Paula created this essentially con artist persona because a man who lived with his parents broke her heart. But later Paula is shocked to learn why Tripp lives at home: His life collapsed when his fiancée suddenly died, and his family has been his solace ever since.
Ace discovers Paula’s profession and therefore that she is duping Tripp, so blackmails Paula for a date with Kit. Although Kit is more attracted to Demo, she and Ace fall in love. Ace then “outs” Paula to Demo, who then tells Tripp.
Tripp angrily confronts his parents and Paula over the scam and breaks up with her. Wracked with guilt, Paula refunds Al’s and Sue’s money. After an awkward confrontation, Tripp has moved out and taken up residence in the sailboat he had been saving for. Over time he forgives his parents, but can’t forgive Paula.
Tripp’s parents and friends devise a plan to reconcile the two. They tie up and gag him, locking him and Paula together in a room. Paula pours her heart out, and he finally forgives her.
Al and Sue are finally in their empty nest, happily singing “Hit the Road, Tripp”. This fades into the closing credits over the Ray Charles song “Hit the Road, Jack”, as Tripp and Paula sail away on his newly purchased boat.
Don’t miss out on the heartfelt comedy of Failure to Launch! Watch free now and experience the ups and downs of love, forgiveness, and new beginnings.