When his skateboard-deck business venture hits the wall, 20-something graphic designer Ben agrees to fund a 'sure thing' leather-jacket hustle proposed by his good-times best friend, Cam. The partner's scheme morphs into downright desperation when Cam's cousin Rene gets out of jail, looking for payback of an old loan. Meanwhile, Ben is bummed to discover that his ex-girlfriend Rachel is now dating a hot hotelier named Darren, and finds little comfort in his horny pursuit of a sexy young thing during her late-night party. With Rene threatening bodily injury if Cam and Ben don't pay back the loan, a schoolmate-turned hedge-fund millionaire named David ends up saving the day...at least for the moment.

Using $3G they got via yet another (very) high-interest loan from Rene, Ben and Cam buy up a roll of (hot) premium-denim material, then hit a series of dead ends in their search to find a manufacturer to make samples of their 'Crisp' brand of retro-70s jeans. Along the way they parlay a crashed late-night dinner with a top fashion designer into a brainstorming meeting that may, or may not, hold the key to their entrepreneurial success. Meanwhile, both Ben and Rachel realize that they haven't totally 'moved on,' and vow to try harder in the future.

While Ben and Cam track down a tailor to re-imagine some 1970s-era jeans, Rachel (who works at an interior-design boutique for an eccentric boss named Edie) rethinks her future after reconnecting with a friend who works abroad for the Peace Corps. Eager to get a bigger marketing commitment for his fledgling 'Rasta Monsta' drink, Rene makes a buyout offer his marketing partners better not refuse. After Cam peddles some of Ben's skateboard decks to some upper-crust Manhattan kids, he and Ben round up enough money to pay the tailor, deliver the denim, and launch 'Crisp NYC.'

In an attempt to divert himself from the depressing fact that it's Rachel's birthday and she's being thrown an intimate dinner party attended by her new squeeze Darren (a handsome hotel developer), Ben decides to spend the night taking Kaplan to a velvet-rope nightclub. Meanwhile, Cam lands a high-paying gig bartending at a gala benefit, but decides to forfeit the job to keep a forlorn Ben--and Kaplan and Domingo--company.

After running into a successful designer on the street, Ben and Cam get hooked up with a top Japanese buyer named Hidemi, but find their business taking a surprising detour after showing him their none-too-Crisp jean sample. Meanwhile, Rene runs into some unexpected problems locating a pile of stashed cash in the basement of a woman who is divorcing his ne'er-do-well cousin Tito. And Rachel, hoping to bring some fresh energy into her relationship with Darren, is flummoxed by his euphoric reaction to the party drug Ecstasy.

Despite a fresh infusion of cash from Kaplan, Ben and Cam find it hard to meet Hidemi's vintage-tee quota of 300--until an attractive retail employee named Julie helps bail them out. Rene gets some fatherly advice on how to handle an impending schoolyard showdown with Flaco, the contractor he suspects of stealing his (ill-gotten) money. Rachel's field trip to Connecticut to check on a behind-schedule carpenter ends with Darren taking her to meet his mother Barbara--and then popping a commitment question on their drive home to Manhattan.