Playing by Heart is a 1998 film by Williard Carroll that tells the the interwoven story of a group of couples as they work their way through their various relationships.
Paul: You know, I never knew what love was until I met your mother. And by then it was too late.
Mildred: I never loved your father. Not for a minute.
Mark: Wow. You're...good at this.
Mildred: I was so relieved when he died.
Mark: Geez Mom, don't hold anything back.
Trent: Have dinner with me.
Meredith: Look, I'm not going to sue you or anything.
Trent: I'm not asking as a pre-emptive strike against litigation, I'm asking--
Meredith: I'll have dinner with you.
Trent: What changed your mind?
Meredeith: Anyone who can say 'pre-emptive strike against litigation' with a straight face deserves a dinner companion.
Paul: What are you thinking?.
Hannah: Hot liquids and facial burns..
Hannah: And you really didn't sleep with her?.
Hannah: And you didn't want to sleep with her?.
Paul: Good G-d, yes, I did..
Joan: I said you look like a man in need of a coke..
Paul: If I have to wear a tux, she has to wear a bra..
Meredith: They look so perfect together..
Hannah: They look so perfect together..
Paul: Just like we do..
Meredith: This is gonna sound really weird..
Trent: You're worried about Barley, and you want to go back to your place..
Meredeith: Oh my G-d, this is way fucking spooky..
Hugh: I lost my wife and kids..
Allison: Ask the bartender, he can find anything..
Hugh: I should be alone. Alone in hell. That's where I am..
Joan: (on the phone) The lad doesn't say much, and when he does, he finds just the right words to crush my soul. Of course I'm crazy about him..
Joan: She's got her eye on you..
Keenan: Yeah, but it's her good one..
Keenan: That is the ugliest cat I've ever seen..
Joan: She's an angel..
Keenan: She only has one eye..
Joan: Yeah, but it's her good one..
Joan: You should write these kiss-offs down. How to crush a woman's soul in ten words or less. That was ten, wasn't it? (counting) You're-terrific-Sensational-really-but-I'm-not-right-for-you. Yep. Ten..
Gracie: Don't be an angerball..
Meredith - Gillian Anderson.
Trent - Jon Stewart.
Paul - Sean Connery.
Hannah - Gena Rowlands.
Mark - Jay Mohr.
Mildred - Ellen Burnstyn.
Joan - Angelina Jolie.
Keenan - Ryan Phillippe.
Hugh - Dennis Quaid.
Gracie - Madeline Stowe.
Roger - Anthony Edwards.