Worst Date Ever

by J. S. Cooper

  “What are you thinking about, Izzy?” he panted.

  “I don’t know,” I said. “What are you thinking about, Jack?”

  “I’m thinking about how I’d like to take you in the kitchen and fuck you over the kitchen counter.” He laughed. “Give me ten minutes.”

  “Oh, really?” I said. “Do you really think I’m going to allow you to do that?”

  “I bet I could talk you into it.” He reached over and sucked my nipple. “This is fucking hot. You know that, right?”

  “I know that. I’m hot and you’re not,” I laughed.

  He snorted with amusement. “You don’t think I’m hot?”

  “Okay, maybe a little bit.”

  “Yeah, that’s what I thought. You couldn’t find anyone hotter than me, I’m sure.”

  “Excuse me?” I blinked at him. “Are you joking? You don’t think I could find anyone hotter than you?”

  “Maybe. Maybe not.” He shook his head. “So now that you’re here, what do you think you want?”

  “What do you mean what do I think I want?”

  “I mean, now that you’re here in my penthouse, you’ve got me to fuck you, what else do you want?”

  “What do you mean what else do I want?”

  “You’ve obviously been playing games with me this entire night, Isabella, and you probably thought by sleeping with me, you were going to hook me or something? But the charade is over.”

  “The what?” I blinked at him. What the hell was he talking about?

  “I said, the charade is over.”

  “What charade?”

  “You don’t know who I am?” He looked at me with an expression that I couldn’t quite read.

  I just shook my head. “Ah, you’re Jack Morrison?”

  “Yeah, I’m the Jack Morrison.”

  “Okay …?”

  “And now you’ve got me.”

  “Well, for one night.”

  “What’s your game plan?”

  “What do you mean, what’s my game plan?”

  “Are you going to try and take photos of us? Are you going to sell it to the tabloids? Are you—”

  “I don’t even know what you’re talking about.” I sighed. “What is your problem?”

  “I think you know,” he said, as he reached down and ran his fingers along the valley of my breasts. “All of a sudden, you pop up on a dating app, beg me for a date on Thursday night, tell me how much you love football, tell me how much you want to fuck me on my kitchen counter because you haven’t had sex in a while, tell me that you want to make dessert for me. And then we meet, and you’re playing these games. You pretend you don’t know who I am, you pretend you don’t know much about football. All of a sudden, you forget every single conversation we’ve had. And then just because you decide to come back and fuck me, none of it adds up. So I want to know what your endgame is.”

  “I cannot believe I wasted my money on you or fucked you.” I jumped up out of the bed and glared at him. “You know what? This was the worst date ever. You sucked. You absolutely sucked. You know what? I got mine, and I’m gone.” I grabbed the sheet and pulled it off of the bed to cover myself, but it wouldn’t come. He started laughing, as I hobbled into the living room so that I could grab my clothes.

  “Where are you going now, Izzy?”

  “I’m leaving. It’s done. This date is over.”

  “What? Here we go again.” I could hear the skepticism in his voice. “Really?”

  “Really, what? You’re an asshole.”

  “I’m an asshole?”

  “Yeah, you are.”

  “Really?” He stared at me, glaring at me in the living room. “I’m the asshole.”

  “Yeah, you are.”

  I grabbed my bra and panties and then looked around the floor for my dress and picked it up. He grabbed my arm and pulled me to him. I could see his eyes searching my face as if he didn’t quite understand what was going on. I reached up and touched his chest because I couldn’t stop myself. Then, I leaned up and kissed him on the lips.

  “You know what, Jack, it’s been real, it’s been fun, but it hasn’t been real fun. Bye.” I pushed him away.

  I quickly pulled on my dress, stuffed my bra and panties into my bag, and hurried to the door where we’d come through the elevator. I looked around for a button, but I couldn’t find it. I was standing there, pissed off, annoyed, and now embarrassed because I didn’t know how to get out.

  I turned and looked at him. “Can you get the elevator for me, please?”

  He studied me for a few seconds and shrugged. “If you really want to leave.”

  “I do. I think this date is done.” I averted my eyes from his. I was fuming. Literally fuming. I was pissed with him, I was pissed with myself, and I was pissed with Abby. I knew this had been a bad idea from the very beginning and of course, I’d been right.

  He walked over and pushed a button I hadn’t seen. Ten seconds later, there was a beep. I walked into the elevator and glared at him. He stared back, his expression inscrutable. I didn’t know what he was thinking, and I didn’t care. I just wanted to go home, scream at Abby, and forget that this date ever happened.

  Chapter Eleven

  Bank Account Balance: $700

  Days Since My Last Date: hours

  Current Weight: Most probably 180

  * * *

  Quote of the day: “The greater the obstacle, the more glory in overcoming it.” -Moliere

  * * *

  I walked into the apartment still angry as hell. It was four o’clock in the morning. I knew everyone was asleep, but I didn’t care. I went straight to Abby’s room and I didn’t even knock on the door. Instead, I opened it and turned on the lights. She sat up, groggy and confused.

  “What’s going on?”

  “I am pissed as hell at you, Abby!” I said, raising my voice and slamming her door behind me. I felt bad for Emma and Chloe. I didn’t want to wake them up, but at this point, I didn’t care.

  “Isabella, why are you mad at me? What have I done?”

  “Dude, what the hell did you say to this guy?”

  “To what guy?” She yawned. “Do we have to have this conversation now? I was in the middle of a really great sleep. I was actually dreaming that Henry Cavill was taking me on a date, and—”

  “I do not care what Henry Cavill was doing. That dude, Jack Morrison, was an asshole. The biggest asshole I’ve ever met in my life. And—”

  “Oh yeah, the date. I forgot it was last night.” She looked nervous. “So it wasn’t good?”

  “No, it was absolutely awful!”

  “And yet you’re getting back now?” She looked at the Apple watch on her wrist. “It’s nearly time to wake up, and you’re just now getting back? But it was a bad date? I don’t understand.”

  “I knew as soon as I met him that he was a jerk. You know he made a comment to me about Pamela Anderson?”

  “Oh?” She blinked sleepily. “Really?

  “Yeah. He was like, “Oh, why aren’t you blonde? Or some bullshit like that.”

  “Oh, really?” She looked away. “And what else? I mean, you obviously stayed.”

  “Yeah, I stayed and—” I sat down on the bed. “I actually hooked up with him.”

  That woke her up. “You hooked up with him?” she gasped as she sat up. “As in you made out with him, or more?”

  “Girl, I am a born-again virgin no longer.”

  “Oh my gosh, you slut. You slept with him?”

  “Do not call me a slut, Abby. We are not there again yet.”

  “Oops, sorry. I’m just a little bit confused. How’d you go from hating him, to sleeping with him, to now hating him again?”

  “Because he’s an asshole. Everything he says is mean and arrogant and oh, I’m just so pissed off! I knew this was a bad idea.”

  “Was the sex bad?”

  “No, the sex was amazing, like totally amazing! Like toes curling, orgasmic, wonderful.” I sighed
not even knowing what to say. I leaned back on her bed. “Oh, Abby. Why?”

  “I don’t understand. So the sex was good, but then it went bad?”

  “Yeah. Then it went bad. He really thinks he’s all that.”

  “Oh no, really?”

  “Yeah. He was going on like I was some sort of gold digger. Like he was some sort of famous hotshot, just because he lives in a penthouse. And then he was acting like I was playing a game of like, not knowing who he was. Like, who the hell is Jack Morrison?”

  “Jack Morrison.” Her eyes widened. “Oh … I thought he looked familiar.”

  “So you know who he is?”

  “No.” She shook her head quickly. “Not at all.”

  “Well, yeah, he was acting like he was some big deal, but he’s not a famous actor because I’d never seen him in any movies. He is not a famous director because I’ve never heard his name before in my life. I thought maybe he’s related to Jim Morrison, but that was obviously a no. Maybe he’s big on Wall Street. Who knows? And then he was going on about football. Like I care about football, whatever.”

  “Oh, he mentioned football?” She toyed with her hair.

  “Yeah. Why?”

  “Oh, just interesting. And what did you say when he mentioned football?”

  “He was like, “Oh, do you love football?” And I was like, “Yeah, whatever. I love it.” And then he asked me who my favorite team was. And I said the New York Knicks.”

  “The New York Knicks?” She laughed. “You know that’s a basketball team, right?”

  “Oh shit. I had a feeling it sounded familiar, but not that familiar.” I shrugged. “Whatever, we soon changed the subject.”

  “Oh, I’m so sorry that you didn’t have a good time.” She paused. “Well, that you had a good time in the bedroom, but not really.” She shook her head. “I’m still half asleep, so I’m not really sure how you’re feeling about the date. But whatever I did that was bad, I’m sorry. Can I please get a little bit more sleep? I have to wake up early.”

  “Fine.” I jumped up, “But I’m letting you know that if you ever try to set me up on a date again, or have any sort of ideas with regards to dating, please leave me out of it. I’m not interested. Okay?”

  “Okay.” She nodded, “Fine. Night, night, Isabella.”

  “Night, Abby.” I stomped out of her room down the hallway to mine and sat on the edge of my bed thinking. He had been cute, and he’d been amazing in bed. And I guess I’d had no plans on seeing him again anyway. So I didn’t have to stress it too much. But he’d been such a jerk. I wish I’d been able to take him down a couple of notches. Maybe I should have withheld sex. Ugh, or maybe I should have told him that the sex was bad. Oh, well it was too late now. There was nothing that I could do about it. I was never going to see him again.

  I also had to be up early. I was meeting my best friend, Lucas, for a late breakfast and then we were going to go to Connecticut. But he had to tell me about his family first. I really didn’t want to go to Connecticut, but Lucas had made me an offer that I couldn’t refuse. I needed to shower and sleep and put this all behind me because the day was about to start and I had to be on top of my game. Lucas had so much information to give me for the weekend, and if I got it wrong, then it was going to screw both of us.

  And the last thing I needed was something else going wrong in my life.

  Chapter Twelve

  Bank Account Balance: Too little to care

  Days Since My Last Date: Don’t want to think about it

  Current Weight: 700 lbs

  * * *

  Quote of the day: “Jack Morrison is the absolute worst date ever in the history of the world.” - Isabella

  * * *

  “Oh, Isabella darling, there you are.” Lucas hurried up to me, a cup of coffee in his hand, and I gave him a quick hug.

  “Hey, Lucas. Sorry, I’m running late,” I yawned. “Late night.”

  “No worries, doll.” He grinned and gave me the coffee. “I had a feeling that you might be a little bit late.”

  “Oh, don’t say that. I hate to disappoint you. I don’t want to be the sort of person that’s known for being late.”

  “No, it’s not because you’re always late. Don’t worry.”

  “Then how did you know I was going to be late today?”

  “Because I texted you three times and you didn’t respond.”

  “Oh!” My hand flew to my mouth. “I’m so sorry. I didn’t even check my phone. It’s just been a crazy morning.”

  “Yeah, so are you going to tell me about it or not?”

  I laughed and shook my head. “I don’t think we have time. We need to get ready for this weekend, right?”

  “Yeah, we do.” He made a face and grimaced. “I really hope we can pull this off.”

  “You do think we can, right?” The doubt in his expression worried me. If he didn’t think we could, we definitely couldn’t.

  “Well, I think so.” He shrugged. “I mean, I don’t think that my grandparents or my parents are going to want to spend too much time with us, and I think it’s very unlikely that anyone’s going to be questioning us about much. So as long as we know the basics, we should be good.”

  “Okay. Well, I mean, I do know the basics. We’ve been best friends for years.”

  “Yeah, but we’ve got to convince people that we’re in love, not just best friends.” He made a face. “And that’s going to be hard for me.”

  “Well, thanks, Lucas,” I gave him a playful punch on the shoulder. “It’s going to be kind of hard for me too.”

  “Don’t lie, Isabella.” He shook his head. “I know you had a crush on me when you first met me.”

  “That is not true.”

  “Ah, yes, it is. You’ve told me before.”

  “I thought you were cute. I did not have a crush on you.”

  “Yeah, same difference.”

  “It’s not the same difference. And anyway, as soon as I realized you were gay, I was just like, whatever.”

  “Uh huh.” He started laughing. “But let’s remember, no one in my family knows, and they cannot know, or I will not get this inheritance.”

  “So, tell me exactly what your parents know.” I sighed, “Are you sure you want to go ahead with this lie?”

  He nodded. “Yeah, I do. I need this money. I really want to open this coffee shop, and I’m not going to get the money for it unless I show that I’m in a meaningful relationship that looks like it’s going to lead to marriage and kids. My grandparents are old-fashioned like that.” He rolled his eyes.

  “So, okay, we’re going to go to Greenwich, right?”

  “Yep. Greenwich, Connecticut, the land of old money.”

  “And we’re going to spend time with your entire family?”

  “Yep. It’s a huge family reunion.” He sighed. “Which I absolutely hate. I cannot stand my family.”

  “Oh, don’t say that, Lucas.”

  “What? I mean, it’s true. My cousin’s a dick, my parents are full of it, and my grandparents are bigots.”

  “Your grandparents aren’t bigots. You don’t know that, anyway.”

  “Um, I’m pretty sure that they would not be happy with the fact that I’m a homosexual. So what would you call that?”

  “It’s 2021, who’s not cool with that?”

  “I mean, I’m sure they’d say it was fine for other people’s kids and grandkids, but not for me.” He waved one hand dramatically. “How am I going to carry on the family name and who am I going to leave my money to when I die? These are all things that my grandparents think about. These are all things that wealthy families think about.” He sighed. “Completely ridiculous, but it is what it is.”

  “I’m sorry. That’s horrible. It sucks that you have to hide who you are.”

  “I mean, I don’t really see them that much. And hey, I don’t mind hiding who I am to family members that I rarely see if it means inheriting millions of dollars,” he shrugge
d. “Does that make me sound cold?”

  “Kinda does,” I admitted. “But hey. My stomach growled. “So are we going to get breakfast?”

  “Yeah, we can get breakfast. What do you want to get? Like quinoa bowls or something?”

  “What?”

  “I mean, you’re on your low carb diet, right? So I don’t want to make you get pancakes or French toast or—”

  “Ugh, I want pancakes and French toast so badly. You don’t even know. Come on, let’s get them.”

  “But, Isabella, you told me not to let you eat badly.”

  “Ah, fuck it. I already ate bad yesterday. I had steak and roasted potatoes and Yorkshire pudding and—”

  “Oooh, that sounds divine. But where did you have that? Because I know you bitches weren’t cooking that at home.”

  “No … I kind of went on a date.”

  “Ooh, a date! With who, you naughty girl? Tell me more.”

  “Trust me, there’s not much to tell. It wasn’t that good. The guy was an asshole.”

  “Umm, that good, huh?”

  “That good. What about you? Have you been dating anyone recently?”

  “No, I’ve been trying to get my business plan together,” he sighed. “Which sucks because I really, really need a boyfriend, but it can wait until after I have my business.”

  “Okay, so what’s the plan for this weekend?”

  “Okay, so we’re going to go this evening. I figured we’ll take the train.”

  “Okay.”

  “And there will be a car waiting at the train station to take us to my grandparent’s house.”

  “Okay, nice. And are we staying in the same room?”

  “Unlikely.” He shook his head. “My grandparents are old-fashioned, remember? They do not allow boyfriends and girlfriends to sleep in the same bedroom. They don’t even allow engaged couples to sleep in the same bedroom. You have to be married to sleep in the same bedroom.” He rolled his eyes. “Like come on, is this the 1800s?”