Worst Date Ever Read online

  Worst Date Ever

  J. S. Cooper

  Copyright © 2021 by J. S. Cooper

  All rights reserved.

  No part of this book may be reproduced in any form or by any electronic or mechanical means, including information storage and retrieval systems, without written permission from the author, except for the use of brief quotations in a book review.

  Editing by Sarah Barbour.

  Cover Photo by Wander Aguiar.

  Created with Vellum

  Contents

  About This Book

  Prologue

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 6

  Chapter 7

  Chapter 8

  Chapter 9

  Chapter 10

  Chapter 11

  Chapter 12

  Chapter 13

  Chapter 14

  Chapter 15

  Chapter 16

  Chapter 17

  Chapter 18

  Chapter 19

  Chapter 20

  Chapter 21

  Chapter 22

  Chapter 23

  Chapter 24

  Chapter 25

  Chapter 26

  Chapter 27

  Chapter 28

  Excerpt From Worst Boss Ever

  Acknowledgments

  Also by J. S. Cooper

  About This Book

  “Go on a date,” she said. “You’ll love it,” she said.

  * * *

  She was wrong.

  * * *

  It had been one year, two months, and seventeen days since my last date when my best friend Abby decided to sign me up for a dating app. She guaranteed that she could get me the best date of my life within one week. I didn’t really want to do it, but I figured what did I have to lose?

  * * *

  Turns out that I had:

  * * *

  1. $500

  2. My dignity

  3. My patience and

  4. My innocence to lose

  * * *

  Okay, so I didn’t really have my innocence to lose, but believe you me, Jack Morrison was my worst date ever. And I’ve been on a lot of bad dates. Trust me when I say that that was the longest ten hours and 33 minutes of my life. I never wanted to see or speak to him again.

  * * *

  But it turns out you don’t always get what you want in life because Jack showed up the very next day at a family gathering I was attending as a fake plus one. As you can imagine, that was a real pickle. Jack wanted to know why I went on a date with him when I’m dating someone else. But he can’t know the whole complicated truth of the matter. I’m in a fake relationship, and now I’m being blackmailed by the worst date ever.

  Prologue

  “Are you one of those women that doesn’t need a man?” The smug, entitled look on his face made me want to slap him.

  “Are you one of those men that doesn’t know how to give an orgasm?” I retorted. I hated the fact that I could see that I’d amused him.

  “Oh, I’ve given plenty of orgasms.” He smirked. “Is that your problem?”

  “What?” Ignore the urge to wipe that smile off of his face, Isabella, I lectured myself as I studied his handsome face. He seemed like the sort of jerk that would get off on me putting my hands on him.

  “Are you acting like Miss Havisham because you’ve never been pleasured properly before?”

  “Are you acting like Austin Powers because you’re an … idiot.” I finished weakly.

  “That’s the best come-back you have?” This time he did laugh, running his long fingers through his golden blonde hair. I hated the fact that this man was so handsome. It should have been illegal to be that handsome—and that much of an ass.

  “Anything more complicated would have gone over your head.” I resisted the urge to stick my tongue out at him.

  “Well, isn’t this just the best first date ever?” He grabbed his beer and took a large chug. “I bet I can guess why you’re single.”

  “I bet I can guess why you are too,” I drawled slowly and let my eyes drift downwards then back up to his eyes. “Pity.” I gave him my most dazzling smile and sat back feeling proud of myself.

  I should have known it wouldn’t last very long.

  Chapter One

  Bank Account Balance: $1678.39

  Days Since My Last Date: 425 days

  Current Weight: 175 lbs

  * * *

  Quote of the day: “Today is the tomorrow you worried about yesterday”

  —Dale Carnegie

  * * *

  “Who needs men when we have food?”

  I surveyed the feast in front of me. The dining room table looked like a smorgasbord of fatty foods. There were three opened pizza boxes, a basket of fries, a plate full of chicken wings, and a side of spaghetti and meatballs. The smell of brownies baking in the oven filled the air with a sense of comfort, and I smiled in happiness.

  “I feel like I’m in heaven right now.” One of my best friends, Emma, grabbed another slice of pizza and took a huge bite. “This is a real feast.”

  “Well, we have to enjoy our last night of freedom.” I giggled as I rubbed my stomach. “Starting tomorrow, we have to cut out all carbs.”

  “It’s going to be torture.” Chloe, another best friend, helped herself to a meatball and sprinkled parmesan cheese on top of it. “I’m not sure how I’m going to survive.”

  “It was your idea.” Abby stood next to the wall with a glass of wine in her hand and savored a long sip as if it were her last. “I don’t know why we agreed to do low carb for the next 28 days,” she groaned. “Yes, I want to lose twenty pounds, but at what cost to my sanity?”

  “Let’s not worry about it until tomorrow.” I was just happy to be enjoying the evening with my four best friends and roommates. At twenty-eight, we should have all had our own apartments, but living in New York was expensive, and so we rented a three-bedroom with a large closet and split the rent. Chloe got the closet, so she paid the least amount of rent, but she also made the least amount of money out of all of us, so she didn’t mind.

  In fact, none of us minded living together. Our apartment was pretty bomb. We were in Little Italy, which was literally down the street from Chinatown, and our place was gorgeous, even though we only had one bathroom—which was beyond hard with four women, but we made it work. We’d all been best friends we’d been roommates our freshman year at Columbia University, and we were used to sharing small spaces.

  “Oh, Isabella, a package came for you. I put it on your dresser.” Abby’s eyes lit up. “It was heavy. What did you get?”

  “Just some new watercolor paints and a new ceramic palette.” I grinned. “I finally treated myself to some Schmincke paints and some nice squirrel hair brushes.”

  “That means nothing to me.” Abby took another sip of wine. “I thought it was a dildo or something.”

  “What?”

  “Well, it’s been over a year since you’ve gotten any action,” she pointed out with a sly smile.

  I just rolled my eyes. “Don’t remind me. I feel like I’m probably a virgin again.” I shook my head. “I’m all dusty and cobwebby down there.”

  “We all are.” Chloe sighed as she grabbed a breadstick. “What I wouldn’t give for a piece of dick.”

  “Chloe!” Emma giggled.

  “So I have an absolutely brilliant idea!” Abby looked around the table at all of us, a gleam in her eyes. For some reason, I felt like I was sitting at a table at the United Nations. Her expression was far too intense for my liking.

  I’d known Abby since we were 18. That was 10 years. She’d never had a good idea. Well, that wasn
’t fair. She’d had some ideas that were good, but that was a very rare thing, especially when she got excited like this.

  “What’s your idea?” Chloe said, munching on another breadstick.

  “Yeah, come on. Tell us,” I prompted. “What’s the idea, Abby?”

  “Do you really want to hear it, Isabella?” she said with a grin.

  “Yes. That’s why I asked.”

  “Okay, so you know how we all hate online dating apps?”

  “Yeah, can’t stand them,” Emma agreed. “Like, literally can’t stand them.”

  “I hate them. Kill me now,” said Chloe.

  “Yeah, I agree with both of them. They suck.”

  “Swiping is like the devil’s game. It is soul-sucking. But I have a brilliant idea about how we can combat dating apps to make them work for us,” Abby said.

  “Um, okay? What’s the idea?”

  “Well, what if we each create a profile for another person, and we select the dates for each other?”

  “What do you mean?” I could already feel that I didn’t like this idea.

  “I mean, what if we create profiles for each other and swipe for each other? That way, we’re not so invested in the conversations or the men we do or don’t interact with.”

  “I don’t know. You might swipe on guys I don’t like and—”

  “But that’s the whole point!” Abby sounded exasperated. “We’re all too picky. How are we four beautiful young women with everything going for us still single? We have college degrees from an Ivy League university. We all have jobs. Granted, we don’t make a lot of money, but we still have jobs. We’re intelligent. We’re beautiful. And yet, none of us have men, and none of us have any prospects either. We’re too picky.”

  “I definitely think you’re too picky, Abby,” Chloe said with a laugh.

  “And you’re picky, too,” Abby said, pointing at Emma.

  “I guess it’s true,” I admitted.

  The last time I’d been on a dating app, I hadn’t connected with many men, probably because I left-swiped a lot more than I right-swiped. But so many of them seemed dull and boring or unattractive or not funny or immature. I mean, there was a long list of reasons why I swiped left, but maybe, just maybe, I had missed an opportunity with a great guy because I was being too picky?

  “Okay, well, tell me more.”

  “Yay, yay, yay!” Abby squealed. “Does that mean that we’re going to do it?”

  “I didn’t say I’m in yet,” I interrupted her quickly. “I just said, ‘I want you to tell me more,’ and if I like the idea, then maybe I’ll be in on it.”

  “I agree,” Emma nodded, “Tell us more.”

  “Chloe, are you in?”

  “I was in as soon as you said you’re going to help us get a date.”

  “Yep. Okay, so it’s just Isabella I really have to convince,” Abby laughed. “Well, here’s the thing—we’ll each choose a name at random. For example, perhaps I’ll get Isabella.” She nodded at me. “I’ll choose photos of you, of course, and create a profile for you. And then I’ll swipe for you, and then I’ll get a date for you. And that’s what all of us will do. And maybe, since we know each other really well, we’ll know the sort of guys each other should be dating. Sometimes, you need someone else to find the dates for you. That’s why people go to matchmakers, guys.”

  “I guess …” I chewed on my lower lip. I still wasn’t convinced, but what could it really hurt, right? “Okay, so we’re going to set up one date, or we’re going to set up multiple dates?”

  “I think we should just set up one date to start,” Emma said. “That way, we’ll see if we like the choices that we’re making, and if it’s a bust, then we don’t do it anymore. I mean, what can it hurt? We’ve all chosen plenty of crappy dates for ourselves, so what’s one more bad date?”

  “I guess that’s true. But do we get to veto photos that you might choose or—”

  “Nope,” Abby said quickly. “We have no input in the profiles we make for each other.”

  “I don’t know if I like that,” I said, shaking my head, “What if you choose something really fugly or me in a bikini or—”

  “We all have to trust each other,” Abby said, “No one can tell anyone else what to do.”

  “Can we at least see the profiles?”

  “Nope,” she said quickly, “because if we see the profiles and we don’t like something, then we’re going to be nitpicking and la-di-da-di-da, and you know that just is not going to work.”

  “Hmm … I don’t know about this.”

  “Come on, Isabella. It’ll be fun. Come on. You don’t want to become a nun, do you? Or do you,” she narrowed her eyes, “is this your way of telling us that you’re going to join the convent or something, Maria?”

  “Maria?” Was she really mocking me with a joke about a character from one of my favorite movies?

  “You know, like from the Sound of Music? Maria von Trapp?”

  “Oh my gosh, you’re such an idiot.” I shook my head, “Of course, I’m not trying to become a nun. And of course, I do want to get laid, and of course, I want a boyfriend and I want to have fun and I want to go on dates, but …”

  “But you just haven’t met the right guy, right?”

  “Yeah, I haven’t met the right guy. Fine,” I agreed with a sigh. “Let’s do it. I’m in.”

  “Yay. Awesome! Everyone, hands in the middle of the table.”

  “My hand’s dirty,” Chloe complained.

  “Well, wipe it off then.”

  Chloe wiped her hands off, and we all put our right hands in the middle of the table on top of each other.

  “One for all and all for one. Let’s get the best dates possible, girls,” Abby said with a squeal. “Yay, I’m so excited! Let me get some shots of vodka so we can all celebrate.”

  “Should we be taking those shots of vodka now?” I was a little confused, “I mean, none of us have a date yet, let alone a good one. Shouldn’t we save that for afterward?”

  “Nope, we celebrate now, and we celebrate afterward. And then if anyone meets their husband from this, you owe the person $1,000.”

  “What?” Emma screeched. “I don’t think so! I don’t have $1,000 to give.”

  “If you find your husband, he can pay the $1,000. How’s that?”

  “Well, if he’s rich enough to pay $1,000, who am I to say no?” she giggled.

  “You do realize that $1,000 is not that much money, right?” Abby said, shaking her head.

  “It might not be much money to you, but it’s a lot of money to me.”

  “It’s a lot of money to all of us,” I laughed. “None of us are going to be millionaires anytime soon.”

  “Speak for yourself,” Abby sniffed. “You never know. Maybe I will.”

  “Uh-huh. Sure thing, sister,” I started laughing, “Go and get those shots before I change my mind.”

  “Okay,” she jumped up. I sat back and grabbed another breadstick wondering what I had just agreed to. It was either going to be the best decision of my life or the absolute worst.

  Chapter Two

  Bank Account Balance: $1650.32

  Days Since My Last Date: 427 days

  Current Weight: 178 lbs

  * * *

  Quote of the day: “The future belongs to those who believe in the beauty of their dreams.” – Eleanor Roosevelt

  * * *

  “It should not be this hard to find a decent man to date.” I looked at Abby over the tuna tartare on the table in front of us and repressed a groan. I like tuna tartare … but not really. It was one of those upscale, fancy dishes that Abby loved to order that I went along with because I didn’t want to look like a total pleb. I was more of a mozzarella sticks and onion rings appetizer sort of girl, but you didn’t come to a fancy restaurant like this and order mozzarella sticks.

  I didn’t even think they had mozzarella sticks on the menu. And even if I wanted to order mozzarella sticks, I couldn’t becaus
e we were on a diet, which already sucked.

  “Girl, I’m telling you. I can help you find the man of your dreams.” She grinned at me. “Let me help you.”

  “Abby, why should I believe you can help me find the man of my dreams when you haven’t been able to find the man of your dreams?”

  “Well, you know that saying,” she said as she grabbed a wonton cracker, dipped it into the tuna tartare, and took a bite.

  “No. What saying?”

  “We all have the keys to each other’s problems.”

  “Mm, I don’t know about that. I mean, why couldn’t you apply the same skills that you think you have on yourself?”

  “Because, oh my gosh, really? Bella, you know I want you to be happy.”

  “I know you want me to be happy. I want me to be happy as well. I want you to be happy. I want everyone to be happy. I—”

  “Enough, Bella.” She rolled her eyes. “Fine, if you don’t want me to help you find true love and happiness now that you’re thirty—”

  “I’m twenty-eight, Abby.”

  “I know,” She grinned. “Almost thirty and still single. I want true love and happiness, too. This is not where we saw ourselves being at this age, is it?”

  “I mean, I don’t know. I’m kind of happy being young, fabulous, and single. Aren’t you?”