Dumb Luck- A short script

“Dumb Luck”

A short script

Written By Michelle DeSantos


Fade In; Establishing Shot: [a city street, cars honking]

Fade To: Setting: [INT. Neil Drake’s NYC studio apartment…his bedroom at Morning]

Scene 1: [High angle, aerial shot of clothes scattered across the floor, then pan over to Neil and a girl in bed]

Neil is sleeping with his latest hookup at his side; he has a dream of being with Haley.

*Insert flashback scene of Haley and Neil laying in bed as she smiles at him he brushes the hair out of her face.*

Back to the present and Neil’s alarm clock sounds loudly as he jolts up to find the other girl next to him, he shuts the alarm and sits up, his head in his hands. Seeing a picture of Haley and him on his end table he lays it face down and gets up and walks into the bathroom, to start his day.


Scene 2: [INT. Neil Drake’s bedroom]

Neil is dressed for work and putting on his watch as the girl wakes up.

Neil: “Hey babe, I’ve got work, here’s some money for a cab,” he says throwing some her way, and grabbing his briefcase as he goes to leave. “But hey, last night was fun,” he says with a smirk and a wink as he leaves.

The girl sits up, and wraps herself in the blankets, as she goes to get her cell phone from her purse; she sees the picture laid down turning it over she looks on sadly, feeling used.

Girl: “Asshole,” she whispers running her hand through her hair in frustration.

(Molly V.O. – off screen) “There seems to be something said about those who are good outweighing those who are evil, but then again maybe you’ve never met Neil Drake.” (Between scenes 2&3)


Scene 3: [EXT. City Block outside Drake’s Apartment]

Neil Drake is walking out of his apartment, feeling quite pleased with himself, he puts his I-pod on and hits play, as she struts down the block; nodding and throwing a smirk at a girl passing by walking her dog.


Scene 4: [EXT. Outside of a train station]

Upon entering the subway station, he spots a 20 dollar bill, picking it up he puts it in his pocket with a happy grin.


Scene 5: [INT. Train Platform]

The moment he gets down to the platform, the train arrives, as he gives the girl next to him a once over and she smiles back flirtatiously.


Scene 6: [INT. Advertisement Office]

Neil sets into his office looking over some new advertising ads, as his secretary comes in.

Molly: “Good Morning, Mr. Drake.”

Neil: “Morning Ms. Molly.”

Molly: (Noticing the girl in Neil’s latest advertisement campaign) “Hmm classy, something tells me she woke up in your bed this morning.”

Neil: “Oh you know me so well,” he says dramatically with a sexy smirk and a slight laugh. “Do I have any messages?”

Molly: “Personal, yes…Business related, no.”

Neil smiles as she hands him his messages.

Molly: “Can I make an observation?”

Neil: “Of course, maybe even over dinner sometime,” he says looking up at her from his desk with a smirk.

Molly: “I don’t think so.”

Neil: “Why not?”

Molly: “Because the observation I was talking about, doesn’t exactly paint you in the best light.”

Neil: “Well lucky for me, I really don’t care what you think, and if you have a problem with my professional skills, I would be happy to fire you.”

Molly: “Oh do you mean lack there of, and don’t worry firing me won’t be necessary, because I quit.”

Neil: “Molly, wait, come on. I was joking you don’t have to get so serious all the time, you know I’d be lost here without you,” he says with a sarcastic smirk.

Molly: “Oh, I’m touched,” she says sarcastically clutching her chest, “You really don’t get it do you?”

Neil: “Get what?” he says with a sly smirk, flirting with her.

Molly: “You walk around this office like the world is yours, you treat women like their disposable to you, but trust me, I can have a sexual harassment suit drawn up so fast, that you wouldn’t be able to charm your way out of even with the best lawyer money has to buy,” she says leaning over his desk.

Neil: “Why, Ms. Molly is that a threat?” he says getting closer to her, as the desk acts as their only barrier.

Molly: “No, it’s a warning,” she says throwing his mail at him, and leaving his office with a strut.


Scene 7: [INT. Advertisement Office]

Later that night Neil was getting his things ready to leave to meet yet another girl, when he stops to look at the picture of him and Haley on his desk, he then opens his desk draw and takes out a ring box and opens it as he is hit with yet another memory.

*Insert Flashback, of Haley crying as she throws a key at him, and storms out with her bags packed.*

Molly: “Heading out for another fun night with yet another poor naïve girl, Mr. Drake?” she says coming into his office from her cubicle just outside, as Neil hurriedly puts the picture down, and throws the ring back in his desk draw.

Neil: “Don’t you ever knock! — Look we need to get something straight, don’t make the mistake in thinking you can hold your little threat over my head, we both know your credibility is shot, no one is going to back you up, they all love me, I’m a great boss,” He says smirking and leaning back in his chair with his hands out.

Molly: (she sits on the edge of his desk) “Really, what about Karen from marketing, you know the one you stood up every time you asked her out, and Rebecca from printing, the one you only hired because she was pretty and oh gosh and then there’s always Haley (she says picking up the picture of him and Haley) the love of your life who you… cheated on, right?… Yea something tells me neither of those women are very fond of you.”

Neil: (Hearing her name he feels sucker punched) “Who told you about Haley?” he says looking up at her with shock and grabbing the picture from her hands.

Molly: “I have my sources, Shall I go on?” she says standing up, hands on her hips; challenging him.

Neil: “What is it that you want from me, exactly?” he says standing up and leaning on his desk.

Molly: “I want you to stop what you’ve been doing?”

Neil: “What is it to you what I do, and who I do it with? Oh wait, I get it, someone’s a little jealous,” he says touching her chin flirtatiously.

Molly: (She slaps his hand away angrily) “No Jackass, I couldn’t care less about you, but I happen to care about how you treat people, especially people who are a part of my life; (Neil looks on confused) Wow! You really don’t remember do you?” she says laughing and folding her arms.

Neil: “Remember what?” he says curiously with a sexy grin.

Molly: “Haley’s my sister.”

Neil: “What?” he says, his face falling.

Molly: “Well, half- sister but who’s counting right?” she says with a dismissing wave of hand.

Neil: “No, NO, I would have known if Haley had a sister, we were together for 5 years.”

Molly: Really? Or were you just too self- absorbed to even realize I wasn’t around because I was away at boarding school for a special design program. But then again she probably told you that, you just neglected to remember, because you were always too busy thinking about yourself. I’ll try to hide the hurt, (she says touching her heart dramatically). It’s a shame, you had it all, and you threw it away in one night, you’d think you would learn a little something from it, but I guess not,” She says about to leave his office.

Neil: “How is she?”

Molly smiles to herself as she turns back towards him.

Molly: “She’s great! She’s doing great for herself; and somehow she gets more and more beautiful everyday. But that’s none of your business anymore now is it?”

Neil: “Is she seeing anyone?”

Molly: (she laughs sarcastically) “You really don’t get it. You know I feel sorry for you, because one of these days you’re going to wake up in the middle of a life you despise, because the way you treat women is despicable. You’re a womanizing- insensitive- manipulative, excuse for a man- and my sister is lucky to be rid of you,” she says getting in his face.

Neil: “Maybe you’re right.”

Molly: “Oh I know I am,” she says in a whispery tone, folding her arms in satisfaction.

As Neil rushes past her and into the hall to unleash his pain, he closes his eyes as Haley flashes in his mind. *Insert Flashback sequence of Neil and Haley…*

“Naley” Montage:

Their First Meeting; at a Frat party, Haley is walking toward the bathroom and Neil bumps into her not looking where he was going, he apologizes and they both stare at each other as his eyes follow her after she leaves; instant spark; as if in slow motion.

Their First Date; ice cream, they sit at a small table and they talk. She’s laughing at something he says as he reaches over and wipes ice cream off her upper lip. She smiles at him and he stares at her.

Dancing Scene; at a party; they dance together, and she’s laughing as he twirls her.

Play Fighting Scene; In his apartment, on his couch, he’s tickling her and she’s laughing as she tries running away from him, but he catches her.

Funeral Scene; Dressed in black, she’s crying sitting on his coffee table he kneels in front of her and kisses her forehead as he sits next to her and holds her.

Birthday Party Scene; She brings out a cake for him and everyone sings to him, as he just stares at her lovingly.

Move in with me Scene; She comes over all cute and she brought him some homemade food, he smiles at her, and she kisses him on the cheek. She sees him just staring at her and he hands her a key, and she just looks at him shocked. “Move in with me?” he says. She streaks, hugging him.

Vacation Scene; A view of tropical trees and a stranger snapping a photo of them as they laugh and joke around.

She finds out Scene; Haley comes home to their empty apartment, she has some bags from shopping. She gets her coffee and sits at the table as she flips through a wedding magazine for fun. A texting noise is heard, she checks her phone but it isn’t hers. She finds Neil’s phone under the couch with a text message from another woman. Her eyes widen, and she covers her mouth in shock. Neil comes home to find her bags packed. He looks at her with a nervous face. She’s angry but she begins to cry. He reaches for her then pulls back as his eyes begin to water, he doesn’t know what to do. They have it out and the relationship ends. Haley grabs her bags and goes to leave he grabs her and she shoves him off, she throws his key at him as she leaves.

**Conversation Guidelines for Flashback #9; “she finds out scene”

Neil comes home from the gym, to find a very upset Haley sitting in silence. He sees her bags packed, and her tear stained face.

Neil: “What’s wrong?” He says afraid to ask.

Haley: “Why don’t you take a wild guess?” She says looking at him angrily.

Neil: “Haley… I can explain,” he says nervously.

Haley: “Explain? (She laughs) There’s nothing to explain, your little friend called, she wants a repeat of the other night.”

Neil: (with tears in his eyes.) “I’m so sorry, it was a stupid drunken mistake, and it didn’t mean anything,” (he says walking toward her.)

Haley: (she stands up) “Don’t touch me; (she says defensively) what did you think that I wouldn’t find out? That you would go on acting as if it never happened; as if you never cheated. This whole time, I’ve been walking around without a clue as to who you truly are, how could you do this?”

Neil: “I wanted to tell you, I did, but I-”

Haley: “But what? There’s a difference between wanting to tell me, and actually doing it Neil. I can’t believe this is happening,” (she says turning away from him, crying, as she folds her arms across her chest trying to comfort herself.)

Neil: “Haley I was scared, I was so scared that if I told you that I messed up, you would leave me. I wouldn’t be able to handle that,” (he says reaching for her.)

Haley: (turns quickly around) Messed up? This isn’t forgetting to buy milk, or forgetting to make dinner reservations Neil, it’s forgetting that you made a commitment to me. And if you can forget that then I can’t be with you,” She says grabbing her bags and going to leave.

Neil goes to grab her, but she pushes him away and leaves, as Neil sinks to the floor, with is head in his hands.

(Flashbacks end)


Scene 8: [INT. Restaurant waiting for a re-date with the girl in bed from earlier; Kelly]

***Kelly walks into the restaurant and Neil immediately gets up to greet her.

Neil: “Hi,” he says shameful of the way he treated her last time he saw her.

Kelly: “Hi,” she says in a tone of voice that let’s Neil know, she hasn’t forgotten.

Neil: “Thanks for agreeing to meet me.”

Kelly: “Well, imagine my surprise when you actually called, begging for a second chance.”

Neil: “I wasn’t exactly begging.”

Kelly: “Really- well then,” she says turning to leave with a playful smile on her face.

Neil: “Ok! You’re right, I did- kind of beg, a little.”

Kelly: “I thought so,” she says smiling.

Neil: “So- will you stay?” he says gesturing to their table.

Kelly: “I guess so,” she says sighing and giving him a skeptical glare, as he pulls her chair out for her.

Neil: “I’m really sorry about-”

Kelly: “You’re hit and run,” she says smirking and cracking her knuckles.

Neil: “Yea, (he says embarrassed) I acted like a complete-”

Kelly: “Dick.”

Neil: “Yea. I really am sorry. I should have never treated you the way I did.”

Kelly makes an expression agreeing with him.

Neil: “But I’m really glad you came.”

Kelly: “Are you?”

Neil: “Yea,” he says looking at her seriously, “Do you think that we can maybe, start over?”

Kelly: “Well,” she says sighing, “that depends.”

Neil: “On what?” he says with a nervous laugh.

Kelly: “On whether or not you’re paying,” she says taking a menu from the waitress as he looks at her with a smile.


Scene 9: [EXT. Kelly’s Door Step.]

Kelly: “Well, I have to say I’m surprised.”

Neil: “Why?”

Kelly: “That you lasted the whole night, without slipping up.”

Neil: “Thanks for the vote of confidence,” he says with a small laugh.

Kelly: “I don’t need to have confidence in you; you need to have confidence in yourself. You know by first glance you’re a really cocky guy, but it must really suck to lose the love of your life… I’m guessing that’s why you’ve become such a ladies man.”

Neil: “What are you- talking- about?” He says confused.

Kelly: “Neil, I’m studying to become a lawyer ok, cracking the case is a part of my life, (She says with a laugh.) The modeling I do for ads like yours, are just to pay my way through law school. I’m not just some stereotypical blonde bimbo, I do have eyes and a brain. But you’d know that if you looked past my body and actually got to know me. A guy, who still keeps pictures of his ex- in his house, means that most likely he screwed up and can’t get over it. Am I close?” She says squinting at him.

Neil: (laughing with a small sigh) “You’re very perceptive,” he says looking down.

Kelly: “Neil- I won’t be your rebound. I deserve to be with a guy who wants me for me; I won’t be a second rate version of your ex when I know I can have a man that wants a first rate me.”

Neil: “Kelly I-”

Kelly: “Goodnight Neil,” she says kissing him on the cheek and walking up the stairs to her house.

*Insert Haley Flashback; Haley laughing and kissing him on the cheek goodbye when they first met at a frat party.*

As Neil turns to walk down from Kelly’s doorstep, looking at his phone he scrolls through some old pictures of him and Haley, then upon looking up he sees Haley, and she’s laughing and on the arm of another guy, as they kiss he spots a big diamond ring on her finger, and he stands there in the shadows shocked, hurt and alone.

Molly: (V.O. – off screen) “And sometimes, evil doers get exactly what they deserve… For the first night in a long time Neil Drake went home alone.”


Scene 10:

Neil walking home alone down a dimly lit block.


Scene 11: End Scene [INT. Neil’s Apartment; at night]

Voicemail recording: “Hey Neil, its Molly. I hope our little run-in last week didn’t cause you too much heartache. Anyway you’ve got an obligation to your clients and your workers Neil. So…get your ass back to work, and I’ll try and go a little easier on you.”

Neil sits at home depressed and lonely. He hasn’t shaved in a few days and is still in pajamas. He’s drinking away his pain with alcohol. As bottles upon bottles of liquor cover his table, he continues to drink.

*Insert quick flashback- Neil passes by Molly’s cubicle and notices a picture of Haley, and her fiancé Drew on her desk; and next to it is a wedding invitation. Picking it up, it’s as if reality had slapped him in the face, as his eyes become watery.*

Remembering that moment; Neil takes yet another drink.

A knock comes at the door; Neil gets up aggravated and opens it.

Haley: “Hi,” she says looking down at her fidgeting hands.

Neil: (notices her ring is gone) “What are you doing here?” he says looking her over as his heart beats faster; he’s shocked to see her at his door.

Haley: “I don’t know,” she says laughing slightly. “I was engaged, I was engaged to a wonderful man, who has been only good to me, and-”

Neil: “Was engaged?” he says with hopeful eyes.

Haley: “Yes, and now I’m standing here at your door, and I don’t really know why,” she says shrugging as her eyes become watery.

Neil: “I think you do,” he says putting his hands in his pockets as his eyes stare right through her.

Haley: “I guess for some strange reason I just needed to see you, Molly told me you’ve been asking about me.”

Neil: “You know- I never did let you go, I still do love you, and I’m so sorry.”

Haley: “I don’t know if I can believe you,” she says looking up at him through glossy eyes.

Neil: “You can, I swear. Haley you can,” he says grabbing her into a tight embrace.

Suddenly Haley vanishes from his arms, and Neil jolts up from a long sleep; seeing a peacefully sleeping Haley lying next to him, he feels relieved and pulls her toward him as she snuggles against him; her body fades away. Neil wakes up at his table with bottles around him and a picture of him and Haley shattered on the floor, as the sound of the answering machine continues to beep.

-The End-


This is a script I wrote back in college. It was one of the first full ones I wrote. It’s really rough around the edges format wise and even content wise. But I think there is a good story there. I just thought it’d be fun to share.

I attempted to shoot this a few years back. But we never got through the full script, due to scheduling issues. I was so ready, with my organized binder of ideas. I even made my “actors” (and by actors I mean my family and friends) take cast pictures. My photographer brother was even in the process of working on a movie poster for me, I should see if I can dig that up, that would be kind of cool to show you guys. I also had my Neil and Haley characters pose for couple’s photos that served as prop/set photos. (I’ll include a few below) Needless to say the filming didn’t pan out and I was pretty heartbroken. But I did get to shoot a really raw, uncut version of the “Naley” Montage. It’s terrible quality and I didn’t even know to use mics. But I am really glad I have that gem. It makes me feel nostalgic. Mind you this was before I knew the beauty of different angles and editing. #freshman. Hey we all have to start somewhere right? I haven’t gotten consent from my actors to release the footage so a few pics will just have to do.

What do you think of the story? Were you surprised by the ending? Or were you secretly hoping Haley would eventually find her way back to Neil? Tell me all the things! P.S. Molly’s MY favorite character, because you never see her coming!


The actors who played Haley & Neil 😉

Naley evening


*Morals of the story*

Don’t Cheat.

You can’t always get what you want.

Karma will eventually catch up to you.


*All images and script content are of my own merit and brain and are of my own personal property, hope you enjoyed reading!*


2 thoughts on “Dumb Luck- A short script

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