The theme of the film was not the only element that attracted Pfeiffer. "I am a huge fan of Rob's and I thought Bruce would be so wonderful in this part. I think that we haven't seen him do something like this in a long time. He is really funny and really charming."
After Bruce Willis starred in such hit action films as Die Hard and Armageddon, he has now come full circle by returning to romantic comedy. Reiner explains, "what [Bruce] does best are these wonderfully romantic and comedic scenes. He has a natural, real feeling to him."
Willis describes the challenges of the role: "[Comedy] is so much harder than doing any other kind of film because it's just hard to be funny and to take funny dialogue and try to make human jokes out of it. It was an interesting challenge and a great story - a classic story."
He continues, "it is a about the relationship and about the romance...the vulnerability of both characters and what you go through when a relationship is being dismantled. The film captures the breakdown of their marriage at a really interesting time. Ben & Katie are right in the middle of it and you see how it all falls apart."
By emotionally altering, in flashbacks, the way each character responds to situations at different points of their 17-year relationship, Pfeiffer and Willis convey the patterns of the Jordans' everyday lives. Ben and Katie "know each other's moves," describes Zweibel, "the subtleties of talking, or sometimes not talking. It is a routine that two people perfect over time," and Willis and Pfeiffer magically "fit together really well."
Extending this unique pairing are Rob Reiner and Rita Wilson as the Jordan's best friends, Stan and Rachel. Wilson describes Stan and Rachel as representing "different aspects of a relationship with different opinions that we may have about marriage. Michelle's and Bruce's characters are going through something we're very opinionated about - marriage!"
Rachel's character digs deep into the fundamental problems: "Marriage is the Jack Kervorkian of romance - it is virtually impossible to French kiss a person who leaves the new roll of toilet paper resting on top of the empty cardboard roll!" On the other hand, Stan believes that "fear and guilt are what keep society humming. There are no definitive answers in life; it is all an illusion."
Paul Reiser adds to the male perspective as Ben's verbose literary agent, Dave. Reiser states that Dave is "another guy chiming in from the bleachers with bad opinions about what women really need in this world." As a man who believes that fantasizing is not cheating, Reiser states that Dave's job is to make Ben "feel a little bit less of a loser, because at least he's not me!"
Being in a scene with Reiner as a fellow actor and as a director was a wonderful experience for Reiser. "Rob is a great laugher and a great comedy fan."
Tim Matheson who plays Marty, Katie's romantic distraction, agrees with Reiser's philosophy, and has "admired [Reiner's] work tremendously. He is a real chameleon as a director."
In concurrence, Willis adds, "there are scenes in the film where I have to be vulnerable and [Reiner] helped me through those. He is a great director. He really knows the material and would continually come up with jokes and little bits to do."