Sarah is about to meet her first date in more than a decade. Claire Cook gives us a contemporary Everywoman in a big, rollicking south-of-Boston Irish family. Sarah’s widowed father, Billy Hurlihy, with six adult kids, is seeing at least two women—that they know of.She is scanning her neighborhood café for the man with a yellow rose. And he and Sarah aren’t the only Hurlihys with romantic challenges.His lenses would have to be made of plastic or polycarbonate.See more » : The best place to meet a guy is at the supermarket.She goes on a number of dates, but finds herself attracted to Jake (with whom she wants to have sex) and Bobby (with whom she does have sex). JOHN CUSACK plays a tightly wound builder of wooden sculls who over-analyzes himself and his relationships, but allows himself to get involved with Sarah (with whom he wants to have sex). STOCKARD CHANNING plays a middle-aged woman who's fighting time while still in the dating world where she's seeing Bill.She ends up becoming friends with Sarah in their common disdain for dating and its pitfalls.
Although she didn't see it as being perfect, she probably would have stuck it out as what she saw as the "for better or worse" obligation of the wedding vows, that is if her ex-husband, Kevin, didn't end it for what ended up being leaving her for a younger woman.
She is urged by her over-supportive family, comprised of her many siblings, their partners, and her widowed father, to get back into the dating scene, something she has been reluctant to do in not feeling ready.
As such, her most proactive sister in the matter, Carol, sets her up on an Internet dating site.
For Sarah, the only successful couple she currently knows is that of her gay coworker Leo (BRAD WILLIAM HENKE) and his significant other Eric (VICTOR WEBSTER), and her only real prospect, Bob Connor (DERMOT MULRONEY), is off limits to her since he's the father of one of her students.
Unbeknownst to Sarah, Carol has submitted her sister's gussied up profile to an online dating service, resulting in a bunch of losers that only further discourage Sarah about the dating process.