Bachelor Barry Egan is the owner of a marketing company who specialize in novelty items, their most successful being themed toilet plungers. He is somewhat henpecked by his seven bossy sisters who not only tease him on a regular basis but actually act in a very emotionally abusive kind of way about his general lack of social life and interests outside of his job. Barry is very lonely and sometimes gets overtaken by bouts of rage and total anguish.
One particular morning proves to be a turning point. In the space of just a couple of hours, he sees a car accident, finds a harmonium that has been discarded and left at the side of the street, and runs into Lena Leonard, a co-worker of one of his sisters. He thinks that this is a random accident, a coincidence, but is unaware that Lena has actually bumped into him on purpose, having seen him in a family photograph on his sister's desk at work.
Poor Barry can't get a break. He is so lonely that he calls a telephone sex line but rather than being temporarily fulfilled he is extorted by the woman at the other end of the phone. She sends her enforcers, four brothers, to collect on what she sees as what he owes her, which unfortunately complicates his new potential relationship with Lena. It also disrupts his current obsession, which is buying large quantities of Healthy Choice pudding and exploiting a loophole in their marketing scheme that will earn him a million frequent flyer miles. The latter plan was inspired by the true story of a man who earned frequent flyer miles for the rest of his life using this strategy and Barry does not appreciate having his ploy disrupted by the sex worker's goons.
Lena goes to Hawaii for a business trip; Barry decides that he is going to follow her there, finding out where she is staying by tricking his sister into revealing the information, an empowering turn of events because it is usually his sister who is able to manipulate Barry and not the other way around. Lena is delighted to see him and although at first Barry claims that in a bizarre coincidence of fate he, too, has a business trip scheduled in Hawaii that week, he quickly buckles and reveals that he followed her quite deliberately because he wants to speed up their relationship. As this happens, he feels relief and is able to direct his emotions that have been pent up and stifled for so long onto Lena.
After the new couple return home, the four enforcers show up again and they ram Barry's car from behind. Lena is slightly injured in the altercation and Barry is so enraged that he manages to fight off all four men in a matter of minutes. He does not want Lena to find out about the sex line that he used, or why the brothers are after him; he is frightened this will kill her attraction to him. Whilst she is being treated in the hospital he tries to put an end to the fiasco and calls the sex line, demanding to be put through to the supervisor. The supervisor is the owner of the local mattress store, Dean Trumbell. Barry immediately goes to the mattress store to confront Trumbell and manages to intimidate him into leaving him alone. After dealing with the issue, Barry decides that he will tell Lena about it anyway; perhaps it won't seem so off-putting to her if it is all in the past now. He begs her to forgive him, and promises that he will use all of the air miles he has finagled from Healthy Choice Pudding to accompany her around the country on her business trips. She agrees readily, and as in all the best romance movies, they embrace, and it appears that they will live happily ever after.
