Tomcats

A group of men including Michael, Kyle, Steve and others vow to invest in a fund whose final inheritor will be the last bachelor left. They joke about the money, but the pact binds them to a long-term game. The arrangement sets the stakes for the upcoming wedding and future fortunes.

Years after the pact, Michael travels to Las Vegas with Steve and his girlfriend. He misreads a moment of intimacy and kicks her out, triggering a bender. He hooks up with a sultry redhead who dares him to gamble, and he goes on a disaster run of bad luck that drains his money and leads him to borrow from the casino.

The casino intervenes as Michael's losses mount, and he is summoned to meet the pit boss Carlos. Carlos explains the severity of the debt and what will happen if it is not repaid, making clear the stakes of his gambling crash. The encounter underscores that his luck has consequences for the inheritance scheme.

With the latest misfortunes, Michael discovers that he and Kyle are the final two men capable of inheriting the vast fund. He resolves to manipulate Kyle so that Michael ends up with the inheritance. The plan hinges on Natalie, the woman Kyle has never forgotten, and on exploiting Kyle's memory of her.

Michael learns that Kyle has only ever loved one woman, Natalie, whom he met at Steve and Tricia's wedding. This revelation becomes central to Michael's manipulation plan, since Natalie could be the key to controlling Kyle. It also explains why Natalie might become entangled with both men as the scheme unfolds.

Michael approaches Steve and Tricia to locate Natalie, hoping to enlist her in the plan. They withhold that Natalie is a police detective, keeping her identity hidden from him for the moment. The omission adds a dangerous twist to the scheme.

Natalie is working undercover as a streetwalker when Michael encounters her and is arrested for solicitation. During interrogation, he confesses the plan and his own motives, risking her trust and his freedom. Shortly after, he is released.

Natalie visits Michael after his release and agrees to join the plan, but only if she gets half the money. She keeps her detective identity hidden for the moment while setting terms. The alliance blends danger with growing attraction.

Michael and Natalie spend time investigating Kyle to ensure the plan works. They realize they are falling in love, and Natalie begins to see a future with Michael. Despite their growing feelings, Natalie resolves to go ahead with marrying Kyle.

At Kyle's bachelor party, Kyle declares he will not quit womanizing and believes Natalie should be the stay-at-home wife. The statement confirms that the inheritance scheme will face significant personal obstacles. The plan now hinges on outmaneuvering Kyle's tendencies.

Michael is knocked unconscious by a bowling ball on the way to stop the wedding and wakes up to find his clothes missing. He borrows clothes from an unconscious stripper and races to the civic hall, but he is too late and Kyle marries Natalie. On their wedding night, Natalie knocks Kyle unconscious and he wakes to a bag of quarters.

After the failed wedding, Michael claims the fund and settles his debt with Carlos, clearing the financial barrier to the inheritance. The victory allows him to pursue life with Natalie without the immediate casino threat.

Michael encounters Kyle again and, after a confrontation, he believes Kyle is cheating and punches him. Kyle reveals that he has split from Natalie. Natalie, still undercover, and Michael eventually marry, and Kyle ends up with the librarian Michael was with earlier.