After planning and coordinating another successful wedding ceremony, San Francisco wedding planner Mary (Lopez) is hired by catering heiress Fran Donolly (Bridgette Wilson) to plan her society wedding to long-term boyfriend 'Eddie.' She is later saved from a freak accident by local pediatrician Steve Edison (McConaughey). An attraction soon develops between the two, but Mary is crestfallen when she discovers that Fran's fiancé 'Eddie' turns out to be Steve, which causes her to angrily rebuke him for leading her on and going behind Fran's back. Mary is left wondering whether she should continue to plan Fran and Steve's wedding, while Steve is left wondering whether his chemistry with Mary is a sign that he shouldn't be marrying Fran.
This film features examples of:
- The Cobbler's Children Have No Shoes: The eponymous character has a lonely and awkward love life. On another level, she's always dreamed of having a quiet, simple wedding—nothing like the elaborate, chaotic galas she supplies for clients. Of course, she knows firsthand how nerve-wracking the latter can be.
- Death by Materialism: It didn't result in death, but this is what set the wheels of the movie into motion. Steve meets Mary by saving her after she refuses to leave her Gucci shoe stuck in a manhole cover, despite the heavy dumpster speeding at her. It goes into Too Dumb to Live when you look at the dumpster in question and realize that it's pretty high off the ground thanks to the wheels, and she could just get the damn shoe after the dumpster rolls by.
- Disposable Fiancé: Of the "let's call the whole thing off" variety. Worked horribly, as the only person you feel sorry for is the fiancée. The man gets romantically involved with another woman (who turns out to be the wedding planner his fiancée has hired) and then berates her for "misinterpreting" his philandering. He then ignores the whole thing and lets his fiancée plan their wedding blissfully unaware that he's falling in love with the planner (who only superficially thinks of ending the whole thing and never lets her client in on what her fiancé is really doing). Meanwhile, the planner is constantly leading on a childhood friend who is desperately in love with her to either serve to make the male lead jealous, or to boost herself up emotionally as she pines for the leading man. At the last second, the fiancée decides she doesn't want to get married, giving him the opportunity to run after the female lead. With his behavior, it's kind of hard to imagine how either woman wants him in the first place. And the planner is even less sympathetic, because it's revealed she's been the victim of this before, when her fiancé got back with his highschool girlfriend on the night of their rehearsal dinner.
- Drowning My Sorrows: Mary gets quite drunk after running into her ex-fiance and his wife, his ex-girlfriend whom he cheated on her with and is now expecting their first child.
- Held Gaze: This happens in a Meet Cute that combines this with Literally Falling in Love when the eponymous wedding planner, is saved by Steve. Actually, this trope is a prime motivator for the sparking Unresolved Sexual Tension the engaged doctor and Mary display towards each other in the film.
- Hospital Surprise: Played for Laughs. Mary is pushed out of the way of a hurtling dumpster, passes out, and wakes up in a hospital with a doctor leaning over her. Actually, it's a little girl 'pretending' to be a doctor; Mary's rescuer was a pediatrician, and brought her to the children's hospital where he worked.
- Hypocritical Humor: At one point Mary finds herself shouting at the top of her lungs, "And because I am a goddamned professional!"
- I Need to Go Iron My Dog: When self-appointed matchmaker Penny must contrive a reason to abandon the leads at a movie.Penny: I just remembered that I promised my friend's brother's godmother that I would help her change her fax cartridge because she's going out of town tomorrow... on an African safari!
- Non Sequitur, *Thud*: After her near death experience, while in Steve's arms:Mary: You smell like sweet red plumbs and grilled cheese sandwiches... (passes out)
- Please Get Off Me: After Mary is saved by Steve from being nearly smashed by a dumpster rolling downhill when he tackles her out of the way, when he starts asking her questions to judge if she is hurt or not, including asking if she has trouble breathing, she notes that it is hard to breath with him lying on top of her.
- Rom Com Job: Mary is, well, a wedding planner, while Steve is a doctor.
- Super OCD: Mary. We first get a glimpse of it by looking into her wedding planner emergency kit, but her immaculate apartment solidifies it.