What a well written piece!

I haven't seen Can't Buy Me Love, but I'm reminded of a later film, Love Don't Cost A Thing, starring Nick Cannon & Christina Milian.

Cannon's Alvin is also a nerd who plans to enter a science fair with a project he & his nerd friends have been developing for some time. He also works in an auto body shop. When Milian's super-popular, affluent, head-cheerleader Paris brings her mother's wrecked car—which she was not permitted under any circumstances to drive—in for an estimate, Alvin has his chance. Fix her car if she'll date him.

I appreciated the writers avoiding the cliche of entitled cheerleader throwing a tantrum when she realizes she can't afford to fix her mother's car (mom's away on business for a week, so she has a chance to avoid ever revealing that she drove & wrecked it). When Alvin tells Paris that the estimate, however beyond her resources, was a fair one, she just nods: "Yeah. I thought so," she says.

Although some of the details elude me now, I recall the plot proceeded pretty much as you describe the Dempsey film: Alvin gets too big for his britches, shines his friends on with no warning, &, when Paris decides he might be worth hanging out with even after their deal is done, he manages to insult her.

I honestly don't remember if they become romantic partners, or just friends, but I know Alvin managed to make amends to Paris, & to his friends. Satisfactory resolution or not, it seemed like a lighter-weight film than Can't Buy Me Love.