Cherry Jubilee waited impatiently outside the restaurant. While it was true that she had arrived early, she’d been waiting now for almost fifteen minutes, and she was beginning to wonder if the pony she was meeting was even going to show up. She had watched as other couples entered the restaurant - an upscale place called The Wheat and Chaff - and only felt a tiny twinge of jealousy when they did so smiling and clearly enjoying each other’s company.
Her attention was caught by the rare sight of a pony approaching the building alone. She was a pale green pegasus, wearing a sleek dress in a dark green that complemented her coat. It was nothing ostentatious, but enough to indicate that she was dressing up. The pegasus stopped a few lengths away, meeting her gaze. “Cherries Jubilee?” she asked, her voice hesitant.
Cherry nodded. “Just Cherry will do nicely,” she corrected. “You must be Lightning Dust.”
The pegasus nodded. “That’s me, yeah.” She hesitated, letting the awkward silence grow. Her mouth opened as she contemplated and then discarded things to say, before she finally settled on, “Shall we… go inside, then?”
Cherry only let the slightest hint of a frown cross her face before she banished it. No apology for being late. Not off to a great start. But she wasn’t one to give up just like that, so she let it pass. “Yes, let’s.” She replied, gesturing towards the door.
Lightning stepped forward, moving quickly to open the door. She was already halfway through before it occurred to her to do anything different. Cherry could see the moment it happened, when she balked and took a step back, holding the door open with one leg. She smiled awkwardly, letting a nervous chuckle out, but at least she held the door long enough for Cherry to step through.
The restaurant’s interior was softly, comfortably lit. The tables were illuminated enough to let guests see their partner’s faces, but still give them a shroud of privacy. The decor was all ornately crafted dark wood, carved into light fixtures and nature motifs. Just past the door was a unicorn maitre’d in full suit and tie, and waitponies in matching uniforms slipped silently between the tables behind him.
It took but a moment for the professional ponies to usher them to their table, treating them just as if they’d been on time. Cherry kept one eye on Lightning the whole way, noting the nervous flutter of her wings and the way she kept looking anywhere but at her.
When they were seated, she didn’t beat around the bush. “Nervous, dear?”
Lightning jerked her head up, suddenly pale. “No! I mean… no. Why would I be nervous?” She laughed. It sounded very nervous. “Compared to what I’ve done, this is easy.”
“It’s fine if you are,” Cherry said easily, as if she hadn’t heard the objection. “Meeting new ponies is hard. It’s alright. I don’t bite.”
“I’m not afraid or anything,” Lightning said defensively. “I’m just… trying to make sure I get everything right, is all.”
Cherry laughed. “Oh, aren’t you precious. No such thing, dearie.”
That got a hesitant smile. “So… I haven’t messed anything up, then?”
Cherry almost let the truth slip past her lips, but instead she said, “You’re doing fine. Why don’t you tell me a little about yourself?”
Lightning perked up at that. “Oh, sure,” she said brightly, and immediately launched into a story about growing up as the fastest flyer in her town. She told it so smoothly that it must have been one she’d told many times before, and all awkwardness was suddenly forgotten.
Cherry hadn’t been expecting that, but she let the story play out. It was a surprisingly good story—many ponies couldn’t string a narrative through their lives, but Lightning could, and she told it with the aplomb of a showpony. And then, suddenly, she stopped.
“And then what?” Cherry asked, invested now. “Did you get into the Wonderbolts?” She paused, and realized what she’d asked, and the obvious answer if Lightning was here. “Oh, I’m sorry, I didn’t mean—”
“No, it’s fine,” Lightning interrupted. “It doesn’t matter. If the Wonderbolts couldn’t see what I was capable of, they don’t deserve me anyway.”
Cherry’s gaze softened. “And when that didn’t work out, you fell into this,” she said softly. The story may have been different, but the ending was all too familiar.
Lightning nodded. “Yeah. I don’t know much about anything, but at least I’m still hot. Seems that’s all you need.”
“Well, the ability to talk to ponies helps.”
Lightning flushed, apparently remembering her earlier nerves. “I’m not… that bad at that, am I?”
“You aren’t,” Cherry replied, and was surprised to find she meant it. “So long as you forget who you’re talking to.”
Lightning looked away, trying to hide her flush. “I just… I’m new to this, and I haven’t really been on many, like… dates.”
Cherry smiled softly. “They probably wouldn’t have helped. An escort’s job is to make her client feel valued, not find romance. Dates are surprisingly poor practice.”
“Yeah, well, you sound like you’ve got a lot of experience with both.”
Cherry didn’t have an immediate response to that, but was saved from having to formulate one by the arrival of the waiter to take their order. Lightning let her order first, and then ordered a dish that was slightly less expensive. Cherry nodded approvingly. Apparently she had retained at least one tip.
By the time the waiter left, she had some idea of how to address Lightning’s accusation. “You’re right,” she said. “Back in the day, I had my pick of any stallion I cared to name. It wasn’t all it’s cracked up to be, let me assure you. And, of course, you can see how well that worked out for me.”
Lightning considered that. “Just stallions?”
Cherry smiled, just a little smugly. “Oh, I’m sure I turned the head of a mare or two as well. But I was always more interested in chasing the stallions. I didn’t need to explore anything else. And then before I knew it, I didn’t have much of either.”
“And now you’re here, paying for company,” Lightning sighed. “Sorry all you got was me.”
“Free advice, honey? Don’t bring that up. You’ll get better tips.”
“Heh.” Lightning grinned. “Which part? The fact that you’re paying me, or that you’re not getting your money’s worth?”
“Either, you cheeky thing.” And now Cherry was smiling too, unable to help herself. This mare was doing absolutely everything wrong, and yet she found herself enjoying the pegasus’s company.
Lightning actually stuck her tongue out at Cherry, seemingly very pleased with herself, but was saved from having to come up with a comeback by the arrival of their food. For a time, the conversation stalled as they ate. Cherry took the time to reevaluate the pony across from her. A strange combination of brash and nervous, with none of the flirty confidence she would have normally expected. She showed up late, forgot basic manners, and freely admitted she didn’t know what she was doing. Everything she would have told somepony in her position to avoid.
And yet, for some reason, it seemed to be working.
“Lightning…” she finally spoke again. “What would you want to be doing, if you had as many bits as you wanted?”
The pegasus considered that. “Found my own flying team, probably. No way I’m going back to the Wonderbolts after the way they treated me, but I’m sure there’s plenty of good flyers out there that don’t want to be Wonderbolts, for one reason or another.” She gave Cherry a hard look. “Why do you ask?”
Cherry took her time responding, circling one hoof on the tablecloth. Finally she said, “I could help with that. If you did something for me, call it a commission, I have the bits to help fund something like that.”
Lightning narrowed her eyes. “What’s the catch? I’m not gonna do anything physical, the terms—”
Cherry shook her head. “Oh no! I wouldn’t dream of trying to pay you for that. But… well, you’re on to something, and I think my girls could learn a thing or two from you about the value of being earnest.”
Lightning blinked, confused. “Your girls?”
“Oh yes,” Cherry smiled mischievously. “I run Cherry Hill Ranch. We’re very popular with lonely stallions… and a few mares, too. I’ll pay you twice what that scoundrel Hard Rock is paying you to come give everypony some fresh ideas, and if it works out, we can look into, shall we say, expanding our investments.”
“Wait wait wait,” Lightning muttered, food forgotten. “You just hired me so you could poach me?”
“Not at first,” Cherry said. “I just wanted to see the competition for myself. But you’re right, cutie. You are pretty hot, and more importantly, you’re genuine. That’s something my establishment has been missing.”
“So you’re saying, all I have to do is come do exactly what I’m doing, but for you instead, and you’ll fund a flying team? I mean, yes? Sign me up!” Lightning extended a hoof across the table to shake. Then she frowned. “Wait, are you hitting on me?”
Cherry laughed. “Perhaps I am. And we can discuss the joint business venture in more detail after. But come talk to my girls, and I’ll pay you either way. Deal?” She extended her hoof as well.
It didn’t take more than a moment for Lightning to shake it. “Deal!” She laughed softly. “Hard Rock was kind of a creep anyway.”
Cherry couldn’t agree fast enough. She returned to her food, and soon the conversation became more relaxed. It drifted slowly from topic to topic, as Lightning became more comfortable and Cherry left the business talk behind. And perhaps let herself flirt a bit more, if only because flustering Lightning was fun.
By the time the evening was winding down, they were both pleasantly full of delicious food. Their plates were long emptied, but the talking and laughing continued, until finally they were forced to admit that it was past time to leave.
“This was fun,” Lightning said as they walked out the door. “I was kind of expecting it to be… work, I suppose.”
“It usually is,” Cherry noted. “But that doesn’t mean you can’t have fun with it. Especially if you’re in pleasant company.”
“Heh, that might be the first time I’ve been accused of that.”
“Don’t sell yourself short,” Cherry smiled. “I had a wonderful time. I was expecting to meet a business rival, and instead met a friend.”
Lightning smirked. “Do you flirt that hard with all your friends?”
“When you come by the ranch, perhaps you’ll find out,” Cherry replied, her voice flippant and a wide grin on her face. “We’ve got a lot to discuss, after all.”
Lightning gave her a grin and a lazy salute. “Will do, boss ma’am.” She spread her wings and lifted off the ground, heedless of the dress she was wearing.
Cherry watched her go. This had been an interesting night. And with any luck, it would lead to many more.
