Tradeoff

Jack was bumbling through life as a young boy. Then, some good advice from an uncle put him on the right path.
Jack then works hard and develops the tools that he needs for the life that he wants. As a result, he gets a job in a stock brokerage in New York City.
Jack works hard at work and also is working nights to try to get a college degree.
Jack then takes a week's Valentine's Day trip to Mexico, with other well to do New Yorkers.
Jack's date, Linda, dumps him, but he then manages to snag Gwen.
Gwen has been dumped by the guy who snagged Linda. Gwen is really depressed.
Jack then slowly manages to convince Gwen that she's a much better date for him than the better looking Linda. Jack also manages to sexually dominate inexperienced Gwen.
Gradually, Gwen begins to see Jack as a long term partner.
Gwen's social skills quickly allow Jack to see her as a long term partner.
There are some problems, but the couple work through the problems and a real bond forms.
The trip back home is then a critical test for the relationship.