Underneath a classic good-girl and street-wise Don Juan romance, LOVE THE HARD WAY reveals itself to be a keen examination of love and emotional dependency amidst the social divergences and congruent rhythms of New York City.
Love the Hard Way begins when Claire (Charlotte Ayanna), a goal-oriented graduate student, meets Jack (Adrien Brody). At the same time unimpressed and intrigued by his bad-boy persona, Claire eventually agrees to meet him. Attraction quickly turns into infatuation and love.
In contradiction with Claire's valedictorian past, Jack runs a regular scam conning foreign businessmen with his partner Charlie (Jon Seda) and two struggling actresses. But Jack's self-conscious rebel stance is much more than a façade, it stems from the books he avidly reads and it ultimately replicates a passion with life which he seems to lack in his daily engagement with life.
Even though Jack is thoroughly charmed by Claire's acute intellect, he pushes her away, just like he did with previous partners. Abandoned and traumatized, Claire begins to neglect her studies and throws herself into a self-destructive downward spiral.
As Detective Linda Fox (Pam Grier) efforts to expose Jack and Charlie's scam intensifies, the once self-assured Jack finds his world crumbling.