Trama

Duncan navigates the unsteady world of romance and relationships, going through five girlfriends in four years. Unfortunately, none of them turn out well.

After yet another failed relationship, 30-something Duncan (Brendan Patricks) decides to quiz his last five girlfriends to find out what went wrong in order to figure out how to find love. With advice from bizarre sources and intense flights of fancy, finally Duncan realises that love is a battleground where only the fittest can survive.—xJROCKx61

Frustrated, at-the-end-of-his-tether Duncan is writing a suicide note to his last five girlfriends: Wendy, Olive, Rhona, Natalie, and Gemma. He blames them all for ruining his outlook on life and love over the past four years and basically rendering him unable to live in a world where true, simple, long-term love does not exist. With the note finished, he ingests a packet of pills and collapses. The film then goes back over the past four years...

Wendy: Duncan meets her on a plane, and the two develop a relationship. Things go well, but then upon the arrival of Wendy's ex-boyfriend Paul, they start to drift apart. Duncan tries his best to keep it going, but finally concedes that Wendy still has feelings for Paul and he himself never really had a chance; he was probably just someone she'd taken up with until Paul came back.

Olive: Duncan finds her an unreadable enigma, and is unable to find out what her exact tastes and likes are. Things come to a catastrophic end when at a dinner with her, he ingests a chocolate pudding, finds it indigestible, vomits it all over the place, and revolts her.

Rhona: Duncan's relationship with her is based on their differences, rather than their similarities: He finds her attractive in an unconventional and exotic way. But when she buys a pair of shoes that she thinks are beautiful but in Duncan's opinion are awful, they ultimately have to confront their differences. Neither of them are willing to keep quiet about their feelings and tastes, nor are they willing to compromise, so they break up.

Natalie: Duncan meets her at a party and they spend the night together. They hit it off well, each one copying the other's mannerisms and even developing their own private language. Unfortunately' neither is willing to commit to a long-term relationship, nor on Duncan's assessment would they be able to maintain their attachment for that long.

Gemma: Duncan's longest relationship. He met her at a party with Natalie, and developed an attraction toward her (which partly contributed to his failure with Natalie), and the two now get together. They complement each other, they enjoy and understand each other, and they have long-term plans together. Duncan deeply enjoys this relationship... till at a party he introduces Gemma to his coworker, Will. He leaves the two alone together and goes home, but later believes that he "let" Gemma sleep with Will. He tries to ignore his suspicions and distrust by taking Gemma to Paris, but it's a complete debacle when she confesses to him that he was right, she DID sleep with Will. Unable to stay with Duncan after betraying him, Gemma ends the relationship.

Now out of his mind with despair and disillusionment, Duncan writes his suicide note and swallows his pills. However, he survives his suicide attempt because he mistakenly took non-lethal tablets; he also realizes that the point of his suicide was to make a point (how love has ruined him), which is useless since he wouldn't even be around to see if it worked or not. He instead throws himself into his work and spends more time with his friends, and is able to make his life worth living once again.

The film ends with Duncan swearing off women and relationships, since he's found it all too complicated and painful to be worth the effort... and then he meets his neighbor, Angela.