At Jane's place, we get a quick glance of the coat closet that holds all of her bridesmaids dresses. Since there are so many of them and a few of them have pouffy skirts, it's almost impossible for her to shut the double doors. There are several hooks on the inside of the doors that hold purses and hats. Her idea of unwinding after a big day is sitting down and reading The New York Journal's "Commitments" section, which is articles about people getting married written by a Malcolm Doyle. The wedding-obsessed Jane loves reading about couples' upcoming nuptials and how they met.
Well, guess what? The next day we see that Kevin works at The New York Journal. (Do you think it's a mix between The New York Times and The Wall Street Journal? Because if you do, you would be totally wrong.) He's Malcolm Doyle. He's the one that writes the romantic and heartfelt stories that Jane loves so much. I do appreciate that the movie doesn't make this some stupid "twist" for the audience to find out later; they tell you who he is in the scene after we see Jane reading that section of the paper. Now, she won't find out for awhile, but for now, the audience knows who he is. Kevin tells his boss he's got a great idea for a story and is hoping it will get him out of writing for the Commitments section because he hates it and wants to be writing "real" stories. His boss agrees and tells him he has one chance to write a story that will impress her.
At Jane's job, she sees there are a basket of flowers on her desk with no note. She thinks they might be from George. Everyone she works with knows she has it bad for him. Everyone but George that is.
One of Jane's co-workers/friends, Casey, is played by Judy Greer, and I admit, when I first saw her, I immediately recognized her but I couldn't think of her name! I did eventually remember it a few minutes later, but it made me think of this commercial she was in about a year ago, you know the one where she goes, "What is my name?" I'm sorry that I almost forgot your name, Judy Greer!
Jane's beautiful younger sister, Tess (Malin Ackerman), comes to visit. She's been living in Italy for the past six months where she designs handbags...I think? I'm not sure. All I know she's involved in the fashion industry because she mentions that "the fall fashion shows are done." She's staying with Jane and calls her apartment "tiny and cute" and there's no way that apartment would be considered "tiny" for NYC!
At the party, George asks Jane if she got "that thing" he left on her desk that morning and she gets excited, thinking he's talking about the flowers, but later, she'll realize he was referring to a dry cleaning slip he left on her desk. Ouch. To make matters worse, her beautiful sister with her beautiful blonde hair (damn that Malin Ackerman and her Swedish-born beauty!) comes sauntering in the room in a beautiful dress and catches the eye of George. These guys hit it off fast and I mean fast. Jane sees it happening right in front of her and she is devastated, but she doesn't let it show. It gets even worse when Kevin shows up (since he had her FiloFax, he knew about the engagement party) and asks Jane if she got the flowers. Yeah, I knew they were from him. He returns her FiloFax to her.
Tess and George go out for drinks and Jane starts cleaning her kitchen at three in the morning because her sister still isn't back yet. When Tess comes back, she barely even notices that her sister is cleaning at an ungodly hour and instead asks her if she thinks it's weird that she went out with her boss and Jane says no even though the way she's acting, she's obviously not okay with it. But her sister is oblivious (her head is in the clouds) and tells her she and George are having lunch tomorrow.
Tess wants to know all about George, so Jane tells her that he dropped out of college and "climbed every peak in the world" which makes sense since he "would rather spend all his time outside than anywhere else." He started his business, Urban Everest, from his apartment and turned it into "one of the most eco-friendly, philanthropic businesses in the world." I still have no idea what exactly the business sells or does, but I'm going to say it sells outdoor camping equipment. He also has a dog that he loves more than anything and doesn't eat red meat. Tess is all dreamy, commenting about how he sounds amazing, but Jane is quick to point out that he also has flaws and cites him hating cashews as one. The hell? How is that a flaw? Another "flaw" is that he doesn't wear socks with sneakers, which is a bit odd, but again, who cares. Tess even points out that those aren't flaws.
They have breakfast with their dad the next morning (I should mention their mother died when they were both younger) and he asks Tess how long she's in town. Jane confirms with her that it's only two weeks, but Tess says "It depends on how a few things pan out." This has Jane a little freaked out and at work, she's in a very bad mood because Tess is also there, flirting with George (who called her that morning) and when Jane flips through her FiloFax, she is annoyed that Kevin has written his name and number in several pages of it.
George has a "little brother" who he's a Big Brother for named Pedro, who's probably eleven or twelve. When he introduces him to Tess, she says "Hola, Pedro" in a really loud voce even though he literally just spoke English seconds before. George tells Jane that he and Tess are taking Pedro to his baseball game and invites her to join them. She refuses at first, but he insists that she join them, joking that her boss is a jerk.
At the concession stand, George orders some Cokes and fries and asks them if they want anything else. Jane says she wants a chili dog and asks Tess if she wants one too. Tess says no, replying that she's recently become a vegetarian (probably when she found out George was one!). Of course, this prompts George to tell her that he's a vegetarian too. Tess tells him that every time she goes hiking, she brings her own "homemade tofurky jerky". While all this is going on, Jane is making a WTF face. Probably because she knows her sister isn't a vegetarian and doesn't like the outdoors. George tells her that she doesn't seem like "the kind of girl that hits the trails" and I get it because she wears heels and always has her hair and make up done and is usually wearing outfits that aren't exactly for the great outdoors. She tells him that she loves "all the outdoorsy type of stuff" and I laughed when when she said "like hiking and biking and climbing...up things."
We next get a montage of George and Tess getting closer and Jane having to witness all of it. One evening, before leaving work, Jane notices that George forgot his wallet (it's on his desk under a bunch of papers) and she looks at his schedule and sees he's at a restaurant. She takes a taxi there and when she walks in, there are roses on a table and two waiters lift up a sign that says, "Will you marry me?" George comes out and tells them to put the sign down because "she's not the one." Ouch! Then Tess walks in at that moment and the sign goes back up and George's dog comes out with the ring box around its neck and George starts to propose. Jane is trying to get the hell out of there (I don't blame her!), but a band comes out and starts playing and they're blocking her path. It's all so awkward. Even if Jane didn't have feelings for George, it would still be incredibly awkward as she's sort of unwillingly becomes part of this proposal. You would think George would thank her for bringing his wallet, then wait for her to leave before he started his proposal to Tess. The restaurant appears to be empty, so he must have rented it out for the evening.
Things start happening pretty fast. Tess tells Jane that Malcolm Doyle (and we all know who he really is!) wants to do a Commitments column on her and George. We also find out they're getting married in three weeks! This seems insane because that's probably the amount of time they've known each other, if that! This is because Tess wants to get married at the Boathouse in Central Park because that's where her and Jane's parents got married. She had called several times and there was no availability for eighteen months, but the ninth time she called, she got lucky because there was a cancellation hence the reason the wedding is in three weeks.
While Jane is with the newly engaged couple to order a cake at a bakery, Kevin comes in and Jane asks what he's doing there. He introduces himself to the couple as Malcolm Doyle and Jane is surprised (but not the audience!). She is super mortified when Tess introduces her (Jane) to Malcolm and tells him she's "obsessed" with his stories and that she's his "number one fan". When asked why he said his name was Kevin, he tells her that is his name and he uses Malcolm for the byline so he doesn't "get stalked by the crazy brides." Jane is not happy because he's been lying to her this whole time. She takes him aside to tell him this; he replies that he told her he was a writer but didn't tell her what he wrote. Jane doesn't understand because he writes "the most beautiful things." She asks him, "Do you actually believe in love and marriage and just pretend to be a cynic, or are you actually a cynic who knows how to spin romantic crap for girls like me." He tells it's the latter which probably just enrages her even more!
Later, Kevin comes over to Jane's place and tells her he has to interview the friends and family of the engaged couple. (You would think he would call to make this appointment or ask her to set up a time for an interview when he saw her at the bakery.) Jane isn't too thrilled to talk to him, but agrees to do it for her sister. When he asks how she feels about Tess's "whirlwind romance", she tells him she couldn't be happier.
Kevin sarcastically tells her it makes sense she would want to keep all of them because they're so beautiful. She replies that they're not that bad and he wants to see one that's "not that bad". She picks out an olive green dress which he thinks the color is "vomit". She says the bride told her it would look good on anyone and into his recorder (in front of her, no less!), he states that she's "slightly delusional and will believe anything anybody tells her." She tells him she's going to show him he's wrong and goes to her bridegroom to change into the dress.
While she's gone, he snaps a few photos of all the dresses in the closet and takes one of her when she comes back. He admit the dress itself isn't that bad, but thinks the color is still awful.
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Jane has a lot of fun trying on all the dresses. She tells Kevin she doesn't mind wearing the dresses because she knows it means a lot to the bride and she wants to make her friends happy and she knows when it's her big day, they'll be there for her too. Hmm, could this be foreshadowing? (Yes, it totally is.)
Kevin's boss asks him how his article is going and he tells her he's still working on it. She reads what he has so far and likes it and wants to run it next Sunday on the front page of the section. He wants to hold it a week because he's not quite done with it and tells his boss that Jane is more than "a perpetual bridesmaid" and that "there's a lot more to her than that." He asks for another week and his boss agrees.
A few things are revealed in the next couple of scenes. We find out that Kevin is cynical about marriage because he was once married and his wife left him for his college roommate. Actually, Jane randomly guesses that for the reason why he hates marriage and turns out she was right! We really don't get too much about this backstory.
Also, Kevin finds out that Jane is in love with her sister's fiancé. Jane is meeting George to go over the menu and Kevin needs to talk to Jane about something and he finds out where she is, so he sees her chatting and laughing with George. I don't know if I would surmise that she's in love with him just because they're enjoying each other's company, but whatever, I guess they need it for the sake of the plot. Before Kevin had arrived and interrupted them, George was telling Jane how much he admires Tess because "she's not afraid to be herself" which we all know is a lie! You can tell Jane wants to tell him that everything Tess has told him is pretty much a lie (she's not a vegetarian, she's not a dog person, and she's not a girl who loves the outdoors!), but she just tells him that she's happy that he and Tess found each other.
The next morning they grab breakfast at a diner while they wait for a tow truck to get the car. Some guy comes up to them and remembers them as "Benny and the Jets" from the night before. The waitress pours their coffee and tells Jane, "You're that girl." Jane thinks the's referring to the karaoke bar, but she's actually referring to seeing her in the paper as Kevin's article has come out one week earlier then he expected. Guess his boss didn't listen to him after all! It's a full page article with many pictures (if not all!) of Jane and her many bridesmaid dresses. The caption reads, "Always, Always, Always a Bridesmaid." Kevin tries to explain he told his editor not to run it and that nobody reads that section anyway. Jane is pissed and walks away, but not before slapping him. When she comes home, Tess is there and she's also read the article. She's furious because Kevin wrote, "If Jane is the prototypical accommodating bridesmaid, than her sister, Tess, is cast as the overbearing, overindulged bride-to-be, who at any moment one worries might start stomping around Manhattan, berating fire and swatting planes from the sky." Hmm, have we seen any evidence of this? Tess may be a bit high-maintenance, but I wouldn't compare her to a Bridezilla.
Kevin tries to call Jane many times to apologize, but she won't answer his calls. Not only is Jane angry at him, but she's also angry at her sister when she finds out that, in a very Pretty in Pink move, she has cut up their mother's dress (which her father said she could wear) and used parts of it in her new, more modern dress. Jane is furious that she did that and goes off on her, telling her that she's going to have to tell George the truth about her.
Jane is true to her word and reads what Tess wrote to her, but she has picked photos of her sister that aren't the most flattering. Not that she doesn't look good in them, but while the photos of George show him volunteering at a soup kitchen or visiting the UN, the pictures of Tess are of her flirting with boys or wearing a bikini for a car wash or stuffing her face with barbecue ribs.
Jane ends with the words Tess wrote for her to read: "And today Tess and George still share the same values. Their love is based on a deep understanding and acceptance of who the other person really is."
Things get worse when Casey tries to clear this awkward moment by shooing Jane away and inviting Pedro up to say a few words. He mentions how great George is as his Big Brother and how happy he is that George has Tess who he calls "really cool" because she's going to help him "start [his] own cleaning business." In an earlier scene, Jane had gone to George's apartment where her sister was staying. George was gone for the day and when Jane comes over, she hears a vacuum, and then sees Pedro vacuuming. Tess tells Jane that she's paying him to clean the apartment, but wants to keep it a secret. Guess Pedro was so excited about his new business that he couldn't keep his mouth shut! Boy, George was not happy about that! I think he (maybe) could have forgiven Tess for lying about being a vegetarian, but her exploiting Pedro like that definitely wasn't a good look.
To no one's surprise, the wedding is off and when Tess tells this to Jane, she adds, "I hope you're happy." (For the record, she isn't, but let's be real, I bet she's a little relieved that her younger sister isn't marrying her boss). Jane goes outside, upset, and Kevin is there to apologize since she won't answer his calls. He apologizes and says he wanted to be there for her because he knew this night was gonna be rough for her and tells her he thinks she "deserves to be taken care of for a change." It's a sincere apology and he also gifts her with a Blackberry. He tells her it's "so [she] doesn't have to carry around the crazy FiloFax from 1987." Considering you can still buy FiloFaxes in 2024, I very much doubt hers is from '87! Also, maybe she preferred to carry it around and it's just easier for her to write things down then type it down. I get he meant well, but he shouldn't have just assumed she would have wanted a new phone.
The sisters talk and Tess tells Jane that she stayed in New York because she was fired from her job (still not exactly sure what she did) and her Italian boyfriend dumped her. As she tells Jane, when she met George, he was nice to her and treated her well and she "wanted to be someone that he wanted"; she "was trying to be someone who deserved him, someone he could respect." She basically tells Jane she was trying to be her.
Later that day, Jane gets a call from George who asks her to be his date to some benefit thing (since he no longer has a significant other in his life!) that really doesn't matter. This scene is just so she can apologize to him for what she did during the slide show. It's also so she can quit her job and confess that the only reason she stayed was because she was in love with him. They end up kissing (twice) and realize neither of them feels sparks for the other. Can you imagine kissing someone that you liked and they didn't feel anything for you? Ouch. But luckily, these two kids' feelings are mutual. I didn't like this scene. I get why Jane quits, but I don't know why we need to see them kiss. I guess this is just to show the audience that these two aren't meant for each other. Well, duh. It just seems so unnecessary when we know she's going to end up with Kevin, if anyone.
Speaking of which...they get together and one year passes and the movie ends with their wedding. I've heard some people on podcast reviews of this movie complain that it doesn't make sense that the anti-marriage Kevin would want to get married. Well, he was burned by his first wife, but then he met Jane and his views on love and marriage changed. That's the story I'm going with anyway.
I am a little confused by a couple of things:
1. I Googled a still shot of this scene and counted the bridesmaid dresses. There are 27, not counting Tess's and Casey's. I thought Jane's wedding dress was supposed to be the 27th so shouldn't there only be 26 women modeling 26 dresses? I looked at two rankings of the 27 dresses and both of them had Jane's wedding dress as #1 so they're counting the wedding dress as one of the titular 27 dresses. I suppose if I took the time, I could look at the photo and see which dress wasn't part of the ranking, but, yeah, I'm not gonna do that.
2. After Jane quits her job and before she reconciles with and starts dating Kevin, we see her clean out her closet and throw away her dresses! At least, I assume she threw them away because she's stuffed them into several trash bags. I guess she could have given them to a consignment shop, but I would think she would put them in garment bags if she did that. So if she threw them out, how did these women wear her dresses? Did they have to go out and buy a replica of them? Did she go digging through the trash? (I highly doubt that!) Or did the movie just forget that scene or just not care?
