Suburban Girl (2007)

Based on Melissa Bank's bestseller The Girl's Guide to Hunting and Fishing, Suburban Girl (2007) stars Sarah Michelle Gellar as an ambitious editrix at a small publishing house in New York. She's determined to make it big on her own terms, but her to-do list gets a bit of a twist when she finds herself in a relationship with Alec Baldwin. It's not just the old-enough-to-be-daddy thing that throws her best-laid plans out the window—it's that he's a huge hotshot in the industry, has a chaotic history, and is just a wee bit sickly. Alec's a classic womanizer with a roster of ex-wives and an estranged daughter. Sounds like a real catch for this fine fisher of men, right? Sarah's not sure about the answer to that. But amidst all the confusion, she does make sure to bare some underwear, so at least some of her priorities are in order!