The question alone sounds like a pitch for a romantic comedy. Tam, a self-sufficent young woman able to hold down her beer and beat her brother at arm wrestling, is torn between two guys. Jack is a type-A Corporate America personality who wears three-piece suits and does power lunches. Sal cooks pastries at the local bakery, and spends his lunch break feeding ducks at Central Park. Tam loves Jack’s confidence and authority, but she’s totally sweet on Sal, a man who’s not afraid to show his vulnerable side.
Jack takes Tam to a swanky uptown restaurant where he slips the maitre d’ a few bills to get them the best table. He wants to fly her on his private jet to Madrid over the weekend. But wait! She has a date with Sal this Saturday to view ‘The Dinner Party’ exhibition at the Brooklyn Museum. What should she do? How can she turn down this once-in-a-lifetime opportunity?
You see, a man with money fills her need for financial security. Not that she can’t make it on her own — she’s doing fine selling her clients’ stuff on eBay — but she’s certainly not opposed to getting a nice diamond. On the other hand, Tam could totally feel taken care of by Sal, in a different way. She loves his romantic nature and that he would go out of his way to make her feel safe. Jack just doesn’t feel cushy, you know.
This turning-point — where the above paragraph plays out in a flashback montage over a catchy but sentimental emo song — occurs near the end of the film.
It’s your turn to write the ending.