Dumped by her "soulmate" in a public elevator, Lucy (Monica Potter) embarks on a series of blind dates to try to mend her broken heart. Date #1 is Doug (John Hannah), a nervous and uptight entomologist who finds Lucy's drunken rudeness during their date refreshing, if not exactly endearing. Date #2 is Gabriel (Gael Garcia Bernal), a playwright and veritable Latino lover with a bit too much spirituality and too little substance. Date #3 is Bobby (Anthony LaPaglia), a former pro baseball player who's still caught up in his past celebrity and is a little boy at heart. Date #4 is Barry (Henry Thomas), who barges in on Lucy's bad haircut, hay fever, and overall bad day and then ends their first date getting to know Lucy's parents (Julie Christie and Harold Ramis), yet he somehow manages to morph into a supportive and devoted figure. Date #5 is Luke (David Boreanaz), a hotshot orthopedic surgeon in Miami who wants nothing more than to show off all his best features to Lucy in order to secure her adoration. Hmm, I wonder which one Lucy will pick.
Alternating between the present (her wedding day) and flashbacks from each of the 5 dates, the film is burdened by a hectic and incomplete feel. We never really get to know how any of these relationships go, and sadly we don't really care. Given that Monica Potter (whose brief entrance into films is thankfully long past) has no chemistry with any of her five exceptional male leads (who have all had more illustrious careers than her), the romance tends to flop. Still, it's cute to play the guessing game and I don't suppose I'll ever stop being a sucker for sappy moments.
Overall, a predictable romantic comedy that suffers from a lack of chemistry and bad acting, but is still not a bad way to spend a few hours.