The Cinderella Waitress

Alistair Rowbottom is sitting in a diner. He looks out of place there, too well dressed, not entirely relaxed either. The waitress is Vivienne Rowe and she notices this.

Vivienne wanders over to Alistair, her sneakers squeaking against the linoleum floor. She doesn't bother with a greeting, instead dropping a laminated menu onto the table, her expression one of weary indifference as she looks out of the window. She works long hours and didn't even notice he already had a menu! She then engages vaguely with the customer.

Vivienne: Coffee?
Alistair: Yes, please.
He looks down at the menu he is holding, barely wanting to touch it as it could do with a wipe with disinfectant. Vivienne notices his reaction. She lets out a short, mirthful laugh.

Vivienne: Don't get too excited about the hygiene. It's a diner, not a surgical ward. You want the coffee black or white?

Alistair: Black is fine, thank you.

She doesn't answer, just heads back, thinking about how many more hours she has until her shift ends. Vivienne returns, sliding a heavy ceramic mug across the table. The coffee is steaming, smelling slightly burnt. She lingers for a second, noticing the way Alistair is dressed, too nice for this part of town.

Vivienne: You're not from around here, are you? You've got that 'lost in the wrong neighborhood' look about you.
Alistair: Is it that obvious?
Vivienne crosses her arms, a small, knowing smirk playing on her lips.

Vivienne: About as obvious as a neon sign. Most people who come in here look like they've been sleeping under some cardboard. You look like you've actually slept in a bed with clean sheets.
Alistair: I'm just passing through the neighbourhood.
Vivienne shrugs, her bluntness softening just a fraction as she realizes he's not offended. She glances at the clock on the wall, then back at him. 

Vivienne: Passing through, huh? Well, if you're looking for a recommendation on where to go next, don't ask me. This place is a dead end, and so is everything else within a five-mile radius. You want some toast with that?
Alistair: Toast would be great, thank you.
Vivienne nods. As she turns to head back to the kitchen, she wonders if he’s a journalist or some kind of academic, but she decides not to ask. Not yet.
Vivienne: Toast it is. Don't let the coffee get cold while you contemplate wherever it is you're going next.

While she waits for the toast at the main counter. Alistair discreetly takes a photo and sends it to someone. It returns with a thumbs up emoji. 
Vivienne returns with the toast, butter and jam.
Alistair: I've got a proposal to put to you.
Vivienne looks cautiously back at him:  A proposal? This isn't a business meeting. What is it?
Alistair: I'm Alistair and I'm looking for a date to take to an evening function. I wonder if you would do me the honour of accompanying me?
Vivenne has a rare moment of speechlessness, then replies: Me? You've got to be joking. Look at me, and then look at yourself. You want to take a waitress from this part of town to some fancy event? Who are you really, Alistair?
Alistair: Nothing special. I like your style though. Truthfully.
Vivienne: It sounds like insincere flattery. She looks closely at him. When's this 'evening' of yours?
Alistair: This Friday evening. Can you make it at that time?
Vivienne: Friday... yeah, I'm off by four. If you're serious, I'll do it if you're serious. 
Alistair: Great. Bring with you a set of clothes, as I want to take you to a nice hotel to have a shower and change. Then off to a hire clothing outfit, before we head out for the evening. Then you can spend a night in a nice hotel room all to yourself, breakfast included. I'll pick you up at four. You'll love it, I promise.
Vivienne's intrigued. She hasn't been asked out by someone like him in years, if ever. 

Vivienne: Four o'clock and don't come in a limousine. 

Alistair: I will just bring the Range Rover.
Vivienne rolls her eyes:  Of course you will. Fine. 

As he leaves, Vivienne looks at the empty table, then out the window. She's not sure if she's terrified or excited, but for the first time in ages, she's actually looking forward to Friday.

The day comes and Alistair picks her up from work and off to a swanky hotel. They pull up outside and get out of the car, the valet then taking it away. Vivienne looks impressed, having seen hotels such as these from the outside before, but not from inside.
Alistair: Come along, we have a schedule to keep.
He leads her through the lobby and to her suite.
Vivienne: I feel like I should be cleaning the room, not staying here.
Alistair: Get yourself ready. I'll be waiting in the lounge.

She doesn't take long.
Vivienne: Right. I'm clean and changed out of my work uniform. Now, where's this 'hire outfit' place?
Alistair looks at her, genuinely impressed by how the change in attire highlights her natural beauty.

Alistair: We will drive there soon, but for now, a quick stop at the hotel salon for some make up touches. Not too much is needed as you don't require it. You have a natural look.

They go to the hotel salon and then on to the dress hire boutique. A stylist quickly steps in, draping a deep emerald dress and a shrug over her shoulders. As Vivienne looks at herself in the mirror, the rough waitress is gone, replaced by someone who looks like she belongs in a ballroom. 

She turns to Alistair, a playful, skeptical glint in her eye: I feel like I'm wearing a costume. Do I actually look like I belong at whatever this event is?
Alistair smiles with a genuine, warm expression: You look stunning, Vivienne. Truly.

The compliment catches her off guard, making her blush. They head back to the car, the anticipation building as Alistair reveals the destination: a high-society gala for the arts. As the car pulls up to the grand entrance of the opera house, a few flashing lights from photographers create a surreal welcome. Vivienne feels a surge of nervousness, her hand gripping her clutch bag tightly.

Vivienne: Alistair, there are people with cameras. Why are there cameras?

Alistair: Because it comes with the territory. Just stay close to me. 
Vivienne laughs and takes his hand, stepping out into the spotlight, feeling a strange sense of importance. 

Vivienne: Alright then. Let's go.

They enter, and Alistair is immediately shaking hands and introducing Vivienne. If anyone wishes to engage Vivienne in conversation, Alistair adroitly moves on. They are served drinks and hors d'oeuvres. They then admire the artwork together, Vivienne not entirely impressed by some of the more abstract ones on display.
Vivienne: I don't get it. Why is a red square on a white background considered 'profound? In my world, that's just poorly painted.
Alistair chuckles, leaning in close so only she can hear: That's the beauty of it. The artist claims it represents the isolation of the human spirit. But between us? Nothing special.

They then go to a banquet and are seated. There are another three couples at their table. One woman sitting near Vivienne engages her.
Woman: I'm Melanie. I've not had the pleasure of meeting you before. And this is my husband, William.

Alistair winks at his friend William discreetly, but Melanie knows nothing of William's dare.
Vivienne: I'm Vivienne. Nice to meet you.
Melanie: You look lovely tonight, Vivienne. I've never seen you at any of these events. Where do you usually spend your time?
Vivienne: I'm usually at home. I'm not one for high society events.
Melanie: Oh... how... charmingly honest.
Alistair steps in: She's a breath of fresh air, wouldn't you agree?

The evening continues with a few close calls, but overall, Vivienne carries it off with aplomb. She gets into the spirit of the evening. Then it's back to the hotel, where Vivienne will enjoy a nice suite for the night.

Alistair leads her to the door of her suite and says he will pick her up tomorrow morning. Before he leaves, Vivienne asks him to come in briefly. They sit and Vivienne studies him with an eye that reflects a streetwise maturity.
Vivienne: So, Alistair. Who are you really? And why me? I'm not just talking about the dress or the hotel. I'm talking about the 'why'. Why take a waitress to a gala? You've got a lot of money and a lot of influence. You could have taken anyone. I'm sure you know women who have their own wardrobe of fine dresses and would make the perfect consort.
Alistair: Why did you agree, if my request was so unusual?
Vivienne: Because I've spent my whole life being nobody special. I wanted to see how the other half live. But I'm not naive. This is either a very kind gesture or a very expensive game. Which one is it?
Alistair pauses with a wry smile: Why not just enjoy the evening at face value. Does there have to be a reason?
Vivienne: Yes, there does and I'm a curious person. If I want to know, I should be allowed that indulgence. Wow, I'm even starting to talk posh.
Alistair: Very well, but don't be offended.
Vivienne: I'm a waitress and I get insulted by people. I can handle the truth.
Alistair: Very well. A friend of mine, William, and I watched a movie about taking a working class woman and putting her in a posh event and pulling it off without it being noticed. I said it wasn't that difficult, so William dared me to get someone from a less affluent lifestyle and take them to a posh event to do the same thing. He insisted that it had to be authentic, so I took a photo of you at your work and sent it to him.  He gave a thumbs up. You were an ideal candidate. The rest is what you know.

Vivienne stares at him, her eyes narrowing as she processes the admission: A dare? You're telling me that this whole thing, the hotel, the dress, the gala, was all because of a dare with some posh mate of yours? I'm a pawn in your little game?
Alistair: I'll be honest, that's how it started. But as the evening went on, I realised that you're not just a pawn. You've got a spark, Vivienne. Most people in that room are bores. I genuinely enjoyed the night because of you.
Vivienne leans back, crossing her arms, her expression a mix of annoyance and a strange, lingering curiosity.

Vivienne: You've got a lot of nerve, Alistair. I had a unique evening and it now feels less special.

Alistair: The thing is, I want to see you again. This time it would be for a genuine reason. If you will let me, the next time you have a day off, I'd like to do something with you. Anything you want.
Vivienne: I have a free day on Monday. I'll meet you at the bowling alley on South St, 10am.
Alistair: Deal.
Vivienne: Now, off you got. I have a very expensive bed to test out, and I'm not doing it with you here.
Alistair smiles and leaves.

Monday rolls around and they go bowling, including a meal. They have a great time.
Vivienne: I can't believe you're actually good at this bowling. I thought it would be something you wouldn't bother doing.
Alistair: I'll have you know I was the champion of my school's bowling league for two years. I'm a man of many surprising talents.
Vivienne: I'm sure you are also good at bowling the ladies over.
Alistair: Actually, I'm not good at it. I find the social class scene I move around in more about who can provide what materially than real love. It feels artificial, whereas you're real.
Vivienne: I'm definitely real. I'm the kind of real that doesn't take nonsense from anyone.
Alistair: That's exactly why I like you.
Vivienne: You're not as posh as you look, are you? Underneath it all, you're just as down to earth as the rest of us.
Alistair: So maybe we can spend some more time together? Would you be happy with that?
Vivienne: I'm not saying yes. But I'm not saying no.
Alistair: I'll take that as a maybe. I'll call you on Tuesday?
Vivienne: Yeah. I have that day off too. Call me. But don't expect me to be waiting by the phone.

Vivienne senses that Alistair really does like her, and that puts their potential relationship on a more even footing. She's is the girl from the poor part of town who is desperate to get a better life but she senses Alistair is really falling for her. The keenness, in that case, wasn't all one sided. For once in her life, she felt empowered, valuable, needed. It felt rather nice. 

She might play a little hard to get, but not too hard. Alistair rings on Tuesday and Vivienne decides to ignore it. A few minutes later, another call, and she leaves that one too. Finally, on the third call, she answers. 
Vivienne: Hello.

Alistair: Vivienne. I've been calling you.

Vivienne: I must have been otherwise engaged. 

Alistair: Can we do something today?

Vivienne: I'll just check my diary....I think I might be free. You're in luck.

Alistair: You are a tease. You sense how much I like you and you are having fun with me.

Vivienne: I wouldn't do that, would I? Giggles. So where are we going?