TODD has a long-suffering crush on coworker RACHEL. She's beautiful and out of his league. They both work for an ESPN-like sports network, with her in front of the cameras and him behind.
Todd meets/befriends the new neighbor in his apartment complex, plain-but-pretty SANDRA. She's obviously a better match for Todd but he doesn't see it.
On a company junket, due to an overbooked flight, Todd is bumped up into first class where he sits a few rows behind Rachel and meets DAMON, a mysterious business man who becomes aware of Todd's unrequited love for Rachel.
Damon gives Todd his card. COINCIDENCE BY DESIGN. Their logo is: You Can't Stalk The Perfect Woman, But We Can. Damon pitches his services: for a very expensive fee, they guarantee a number of faux coincidences that will have the woman of your dreams eating out of your hand.
When Todd returns home from the junket, being no closer to the woman of his dreams, he decides to go for it. He confides his intentions to his next-door neighbor Sandra (who secretly pines for him) and she tries to dissuade him.
Todd meets with Damon and hands him a check. The process begins. Over the next several weeks, the company will find out all it can about Rachel and begins arranging fake coincidences, designed for the purpose of endearing himself to her.
The coincidences come in various forms: he bumps into her at the opera (they both love Puccini), she spies him at her gym ('yoga'), he wears a tee-shirt featuring her favorite (but obscure band), he just happens to have tickets to their reunion, etc, etc.
As their relationship progresses, Sandra sees less and less of Todd. Finally, she turns on him. "Love can't be bought! It can't be manipulated! You have all the inside scoop. You know what to say and what to do." She raises the question: Is all fair in love and war?
Now that he's seeing Rachel routinely, Todd has elevated his social standing. He dresses better. Drives a better car. Things are going perfect. But then, Damon suddenly reappears: The fee is now double. Pay it, or we spill the beans.
This is their hook. They deliver on their promises and then blackmail their clients for more money. Todd doesn't have money. Faced with the choice of paying off Damon or having the truth revealed, he takes Sandra's advice and decides to come clean.
It doesn't go well. Rachel is appalled/aghast and dumps him on the spot. The sports network fires him for unethical behavior. And to make matters worse, Damon shows back up at his apartment and threatens to kill him.
As Damon attempts to bully Todd into cashing in his life savings, Sandra bursts into the apartment and there is a huge struggle. She manages to push Damon out of the window where she watches him scream his way down ten stories. Todd takes Sandra into his arms and kisses her. It's obvious: SHE is the one he was meant to be with. Soon, church bells ring and wedding rice fills the air.
In the epilogue, Sandra tells Todd she needs to run some errands. Camera follows her where she makes her way to the pier and sees a group of men playing bridge. One of them is Damon!
Damon looks up, smiles. He's glad to see her. She hands him a check which he politely accepts, folds and places in his pocket. Another job well done.
COINCIDENCE BY DESIGN