- Harry: You must know a lot about love.
- Lucy: I know about dating.
- Harry: What's the difference?
- Lucy: Dating takes a lot of effort. A lot of trial and error. A ton of risk and pain. Love is easy.
- Harry: Is it? I find it to be the most difficult thing in the world.
- Lucy: That's because we can't help it. It just walks into our lives sometimes.
- Harry: You say you think I'm smart, but you're talking to me like I'm a caveman. I wouldn't date you if I didn't see value. I'm not like my brother; I'm not looking for the nicest, prettiest rich girl who likes me back. I'm looking for someone who understands the game, how the world works. I'm looking for someone I respect. And trust. Someone who knows more than me. I don't want to date you for your material assets... though I think you're underselling them by a significant margin. Material assets are cheap, they don't last. I want to be with yoh for your intangible assets. Those are good investments. They don't degrade. They only get sharper.
- Lucy: One day, for no reason in particular, you two will start to hate each other. You'll resent each other, you'll take each other for granted. You'll stop having sex, somehow manage to make a couple of kids. And then you'll get sick of each other, and one of you will cheat on the other. And then you'll fight. At first, not in front of the kids, but then in front of the kids. And then you resent the kids for seeing you fight. And then you file for divorce, and you fight about who owns what and who gets the kids when until it's all over.
- John: You asked how I could love you. I just do; it's the easiest thing.
- Lucy: I love you too. More than you know. You're the only reason I know I'm capable of love.
- John: I've been doing some math.
- Lucy: Yeah?
- John: Yeah. And I'm ready to make you an offer.
- Lucy: Okay.
- John: Here's the offer.
- [long pause]
- John: I love you now like I loved you before. I'll love you till the day I die. It's a lifetime guarantee. And I won't forget it the way I used to, even when things are shit. I'll make a calendar item everyday reminding myself that I love you. I'll be your certainty. It's my final offer. You can't negotiate because I don't have anything else to offer you.
- Lucy: [after a pause, extends a hand] Deal.
- Harry's Father: When you get lost... and I know you'll be lost at times... it's life. When you're lost... the answer is simple. Just go where love is.
- John: Why does anybody even get married?
- Lucy: Because people tell them they should, and because they're lonely, and because they're hopeful.
- Audrey: I don't want to date a liberal, and they have to go to church every Sunday. I don't want someone who likes cats. I'm a dog person.
- Lucy: Is a moderate Democrat okay?
- Audrey: Only republican. I want someone who identifies as a conservative.
- Lucy: Audrey, I don't know if there's a cat-hating, Christian conservative lesbian in most parts of New York who wants to date a closeted 49-year-old with three children. Would you be willing to date someone in Long Island or New Jersey?
- Lucy: Dating is a risk. You took a risk. It's brave.
- Lucy: You're the same as always.
- John: Really?
- Lucy: Uh-huh.
- John: I was hoping you'd say I was different.
- Lucy: Why?
- John: Because if I'm different, I wouldn't be the guy who lost you.
- Lucy: Who our partner is... it determines our whole life... and how we live. Not for one, two, ten years, but... forever.
- John: [after Lucy kisses him at someone's wedding event] What is this?
- Lucy: What is what?
- John: Are we getting back together?
- [Lucy doesn't answer]
- John: Lucy, are we getting back together?
- Lucy: I don't know. I really don't.
- John: So you thought you'd just show up at my door, not have a boyfriend, agree to get in my car, kiss me, fuck me while you try to get over someone else, and then leave me again? Is that it? Do you think I'm worthless?
- Lucy: No, I don't think that.
- John: Am I disposable?
- Lucy: Of course not.
- John: Do you feel bad for me? 'Poor old John can't figure his life out'?
- Lucy: Never.
- John: Then why are you using me?
- Lucy: I'm not.
- John: I'm usually desperate enough to let you. I'm a beggar for you. When I see your face, I see wrinkles, and grey hair, and children who look like you... I can't help it.
- [he sighs]
- John: But as your friend... I would tell you it's a bad idea to be with a 37-year-old cater waiter who still has roommates. I would say... you definitely shouldn't marry a guy that has $2,000 in his bank account in a city he can't afford, who's only still there to keep trying to be a theatre actor because someone told him he was good at it once. So, where does that leave us? Here. At someone else's wedding. I can't give you the wedding or the marriage you want. I couldn't even give you the relationship you wanted. It's been years, and I still can't afford to be with you.
- Lucy: Marriage is a business deal. And it always has been, since the very first time two people did it.
- [last lines]
- John: How would you like to make a very bad financial decision?
- Lucy: I don't want to hate you because you're poor, but right now I do, and it makes me hate myself.
- John: Do you know how hard it is to make you happy? And I want you to be happy. I'm trying, I really am.
- Lucy: I know. And it's almost enough to make me happy. I wish that I didn't care if we ate from a halal cart on our five-year anniversary, but I do. And however much you hate me, I promise, I hate myself more.
- John: I don't hate you.
- Lucy: You do. And it's not because we're not in love. It's because we're broke.
- Lucy: I don't know if I like you or if I just like the places you take me to.
- Violet: You're not ugly, you just don't have money.
- Lucy: Even now... I'm thinking: if I choose to marry you... I'm gonna be sitting across from you in cheap shitty restaurants for the rest of my life. I'll be riding in your shitty car, and living in your shitty bedroom... and fighting with you about 25$. I'm weighing being with you... against these shit tradeoffs. I'm doing math. This is what I'm like.
- Patricia: I know the list looks long but I deserve someone who fulfills all of my criteria. I really do. I mean look at me. I'm a catch.
- Lucy: Patricia, I know that every year you go without having a husband raises your expectations for him exponentially. But that doesn't mean that you're due to get one. And it doesn't mean that you can customize, because this is not a simulation. If the service I was providing you was building you a man then, of course, I could build you a man with everything on this list. But I can't. Because this is not a car or a house. We're talking about people. People are people are people are people. They come as they are. And all I can hope to find for you is a man that you can tolerate for the next 50 years who likes you at all. And you are not a catch, because you are not a fish.
- John: It's just dating. It's not that serious.
- Lucy: Right. Dating is not serious. It's just 'girl shit', right?
- Lucy: You're investing a lot in me, huh?
- Harry: I just want our dates to be romantic.
- Lucy: How expensive a meal is makes a date romantic?
- Harry: Doesn't it?
- James: I said a fit woman in her 30s with a nice smile. She's 40 and fat.
- Lucy: She's 39.
- James: 39 is not 30s. That's 40.
- Lucy: I want to prioritize dating a man who's white at first, but then if we have no luck, we can move on to other races.
- Eleanor: So "whites only," at first?
- Lucy: I mean, technically, I'm open to all ethnicities.
- Eleanor: Eleanor, "technically," you're asking me to set you up with only white men.
- Sophie: Here I was thinking that you worked for me... but the whole time I was working for you. Worthless merchandise... to pawn off to anyone who'd take it. But I am not merchandise. I'm a person. And I know I deserve love.
- Sophie: I don't want to waste my time. I'm not asking a miracle, I'm just asking for the bare minimum. I'm trying to settle.
- Lucy: Sophie, I know how it feels right now. But I promise you, you're going to marry the love of your life.
- Sophie: I don't believe you.
- Lucy: That's okay, I believe it.
- John: Now, I admit, I'm not confident that I can make myself less broke.
- Lucy: You don't need to worry about that. You know I can take care of myself.
- John: Yeah, I know. It's not for you. It's for me. For us. You make me brave enough to admit that I want to be happy, and I want to be happy with you.
- John: And I'm gonna pick up more catering shifts and ask for raise, I'll find a serving job at an actual restaurant, and I won't say no to commercial auditions, even though they're annoying... I'll make an actual effort to find a manager-
- [Lucy cuts him off by kissing him]
- John: ... And I'm going to move out of my apartment, and sell my car...
- Lucy: Don't sell your car.
- John: No?
- Lucy: No, let's just... let's just drive around in it until it breaks down and it won't move anymore.
- Violet: What seems to be the issue?
- Lucy: That's the thing. There is nothing wrong with her. She's okay attractive... okay money, okay educated, okay personality. There's just not a standout quality.
- Harry: So what kind of a person does a matchmaker want to marry?
- Lucy: Well, my non-negotiable's that they're rich. My nice-to-have is that they're mind-numbingly, absurdly, achingly rich.
- [first lines]
- Lucy: Hey! Are you single? I'm a matchmaker at Adore. Please give me a call if you want to meet somebody. We have a lot of great matches for you.
- Harry: Are you hitting on me?
- Lucy: Definitely not. But I do think that you would be a great match for a lot of our clients. We need more straight men in New York City.
- Lucy: You don't want to be with me because I'm not a good person. I'm judgemental and materialistic and cold. I broke up with you because you're broke.
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