One of the biggest challenges for the writers was to create characters to illustrate the various chapters of the book, and somehow weave those stories together.
“Character A is going out with character B, character B is really into character A, but character A is really into character C. Character C is dating character D. Character D is married to character E. Character E works with character F. And so on. That’s what the story is about,” director Ken Kwapis illustrates.
“We made a diagram,” says Marc Silverstein, “beginning with Gigi and Conor.” “It all starts with their first date,” adds Abby Kohn.
Then one couple became nine interwoven stories. Keeping so many characters’ relationships straight might have seemed a daunting task; the job of casting the right actor for each role could have been equally overwhelming.
“In any kind of normal romantic comedy situation, your chief job is to cast two people who have chemistry together,” explains Kwapis. “In this case we had to cast several different people who had to have several different good chemistries with one another. It’s a wonderful test of orchestration. It’s, in effect, a kind of theme in variations. You want a lot of variety and, at the same time, there needs to be some consistency between all the players and all the stories.”
Amazing Actors
Producer Nancy Juvonen was thrilled with the cast. “When we started getting these really amazing actors and actresses involved in the stories, we realized that there was something that each one of them related to about the story that they were telling, in some way or another. They each embraced their character in a really natural way.”
Ginnifer Goodwin
Goodwin was cast as Gigi, the character who is really the catalyst for the overall story. “I loved the concept,” asserts Goodwin. “It felt like something that, when incorporated into your life, could lead to more fulfilling relationships and real self-confidence, because you know you’re dealing with the honest feelings between two people.”
Juvonen knew the part of Gigi was a particularly critical one. “Gigi’s the emotional heart, and she also represents the person we all once were, if we aren’t right now,” Juvonen explains. “Some of us hit it better, some of us were cooler than that, and some of us were probably worse than that. But she wants a mate. It’s worth it to her to call, and call again if they don’t call, and do a drive by, and hope that she might accidentally run into someone. She might make some people a little uncomfortable, but she is so honest and earnest in this pursuit, that you can’t judge her. And Ginnifer was perfect for the role. She’s very smart but also has a wonderfully naive, good-girl quality. She just puts it out there and, in the same way she embraces life, she embraced Gigi.”
Goodwin says she connected to the honesty of the role. “I fell madly in love with Gigi and found her completely endearing,” the actress beams. “Gigi is quite eager to find her soul mate and get married and live happily ever after, but she has been grossly uneducated in the realities of relationships, she’s been taught all the wrong signs and overanalyzes and obsesses about it. She will commit to something and ride that train as far as it will go, right or wrong. She’s very resilient.”
“There are a lot of awkward moments in the film,” Kwapis states, “and Gigi probably has the lion’s share of those embarrassing moments. But she’s always going to open herself up too much and be too vulnerable. She’d rather be that and fail in a sort of fools-rush-in way than never connect with anyone.”
Kevin Connolly
Actor Kevin Connolly plays Conor who, along with Gigi, starts the ball rolling with that first date. “He’s a young, up-and-coming real estate agent. He’s got a pretty decent business but he’s still looking for his niche,” states the actor.
Unbeknownst to Gigi, Conor has someone else on his mind. “Conor’s head-over-heels crazy about Anna. She keeps him on the hook, throws him just enough of a line out there to keep him holding on. He’s got tunnel vision, he’s a little obsessed,” laughs Connolly. Juvonen adds: “We didn’t want Conor be a puppy dog when it came to Anna, but to have him be this guy who really had a plan.”
Scarlett Johansson
Unfortunately for Conor, Anna has other plans. Cast in the role of Anna, Scarlett Johansson offers, “She’s a yoga instructor, an artist, a singer, kind of a free spirit, walking through life with her feelers out. She has a sort of ‘boyfriendship’ with Conor–she enjoys his company but she’s not interested in a commitment with him. She likes having him around, having him flatter her, so she gives him some mixed signals, which frustrates him a lot.”
Drew Barrymore
Anna frequently turns to her friend Mary for advice, though it’s not always the best. Drew Barrymore, who also serves as one of the film’s executive producers, took on the role of the ad sales rep at a local newspaper. “I related to Mary and her trials and tribulations of trying to find the right guy,” says Barrymore. “And I loved the fact that her friends are all trying to figure it out with her in this modern, sometimes unromantic, confusing, technological approach to romance. Not long ago, we were waiting months at a time for just a letter and now we live in an age where everything is instant gratification.”
Says Kwapis, “Mary, Drew Barrymore’s character, is really eager to find a boyfriend, but seems to be a victim of technology. She’s a victim of text mail, she’s a victim of the internet, she’s a victim of voice mail. She’s a victim of everything, as she puts it. She’s being rejected by every technological portal available.”
“Drew really responded to Mary,” recalls Juvonen. “I think Drew herself is sort of befuddled by technology. And she’s certainly a romantic at heart. Mary is in pursuit of a relationship–she’s on MySpace and Facebook–and that’s sort of how she ends up having these potential relationships that don’t go anywhere. The character was really a way to represent technology and dating now, with all these methods that seem mathematical and electronic, instead of just meeting people face-to-face. I think the phone is hard enough, when you aren’t touching each other or looking at each other. But now, to be reading what someone says, pouring over two lines of a text message, asking your friends, ‘What do you think he meant, and does that mean I should call him’ It wasn’t like that ten years ago. The ease with which we can just send off a sexy little message to someone is a little scary. And sometimes fun. This is a new age. We’re breaking new ground.”
Ben Affleck
If Mary and Anna represent those still looking for love, Beth and Neil stand for those who have found it, but aren’t sure if it’s enough. Ben Affleck plays Neil, a photographer who has been involved with Jennifer Aniston’s character, Beth, for several years.
“Neil is a really interesting character,” says Juvonen, “because you assume one thing about him, and it turns out to be something completely different. Neil doesn’t believe in marriage. He’s a photographer; he’s been with his girlfriend for over seven years and he really digs her, but he thinks things change once marriage occurs. Ben is so charming and funny and easygoing; he’s sort of all guy. And that’s what we wanted Neil to be, as well as artsy and a thinker–a very smart, smart fellow.”
Jennifer Aniston
“Beth and Neil have been together for seven years,” says Aniston of the couple, “and he is very content not being married and doesn’t believe in it or understand why it has to happen. But she wants to be married and starts to sort of feel like, ‘Wow, am I being duped'”
“Beth has been dealing with this conceit for a long time and swallowing it because she’s in a fabulous relationship,” Juvonen details. “But she wants more, and it turns out her littlest sister is tying the knot, and she’s doing it very quickly, and it sort of pushes Beth over the edge.”
In their professional lives, Beth and Gigi work in marketing at a spice company with Janine, who is married to Ben, remodeling her home and angling to start a family.
Jennifer Connelly
“Janine is remodeling their house,” Kwapis points out, “but I think on some level what she really wants to do is remodel their relationship.” “Janine is a bit old fashioned in some ways,” says actress Jennifer Connelly, who portrays her. “She hates lying, so for her, it’s really important to be with someone straightforward and honest, to trust the person she’s with. She likes the idea of marriage. She and Ben knew each other for a long time, they were best friends and they got married. After a while, so much of it becomes habit, all that stuff that you’re used to for so long. Now they’re in a rut.”
Ben Cooper
Her husband, Ben, is played by Bradley Cooper. “When Bradley Cooper came in, we were done,” remarks Juvonen. “We just thought, ‘This is Ben, in the best way.’ Bradley was so sincere that there wasn’t anything slimy about the character. He sort of wears his heart on his sleeve.”
“I really wanted to play Ben because he’s so conflicted, so paralyzed by his fears,” Cooper explains. “He’s a lawyer and he’s married to Janine, his college sweetheart. He’s sort of going about his life, going through the motions a little, not really able to take a stand in his marriage. Then he meets this girl and he just can’t get her out of his system. I liked that it’s an honest portrayal of romantic relationships, what people really want and what they do, without trying to sugarcoat it.”
Justin Long
When it comes to women, Alex, played by Justin Long, doesn’t sugarcoat a thing. “Alex is, in effect, the voice of the book,” states director Kwapis.
“My character is sort of an advice-giver,” adds Long. “He’s the kind of guy that is pretty honest, very assertive, speaks his mind. He gets it; he understands women because he’s been through his share of them,” the actor grins, “but he’s never given himself over to anybody emotionally. So when he meets Gigi and she’s in need of his advice–or so he thinks–they embark on a sort of ‘My Fair Lady’-like relationship, where Alex is Henry Higgins to Gigi’s Eliza Doolittle. He tries to make her understand that guys just aren’t that complicated, that if a guy doesn’t call it doesn’t mean that he dislikes her or doesn’t find her attractive. He’s just not that into her. He’s probably calling someone else.”
“Alex is the guy who dispenses the hard truth to female friends,” the director comments. “He’s a restaurant manager, so he’s constantly observing couples in action–people doing the mating dance, meeting, greeting, trying to connect–and he’s figured it out. When he meets Gigi, he decides to take her on in this sort of Pygmalion-like fashion; his job is to get this one core truth into her head, and that is ‘Don’t misread the signals.'”
Juvonen explains further. “Alex wants to observe. He wants to be the guy that has these great quips about relationships, but never really jumps in the pool himself. He sort of skims his toe along the pool and judges everyone else who is actively swimming about and looking like idiots.”
Kris Kristofferson
One character–perhaps the only one in the film–to truly have it all figured out is Beth’s father, Ken, played by veteran actor and musician Kris Kristofferson.
“He’s a fun character because he says what he feels. He’s retired, he’ll say whatever he wants, and I can identify with that,” smiles Kristofferson, who thoroughly enjoyed being part of the ensemble. “It’s a great script and a great cast. The nice thing was finding out what a great crew it is. I couldn’t have asked for a nicer bunch of people.”
Kwapis felt the overall collaboration was right on point. “With all of these different characters, I would hope that an audience could have the pleasure of seeing themselves reflected in several ways, and I think this cast really accomplishes that.”
“Everyone did a really good job of not hitting it over the head, while definitely extolling the virtues of what we said in the book,” declares author Greg Behrendt.
