Chapter 5

Wyatt

“A mix of Bart Simpson and Marge,” Ren said as he typed it into my profile.

“What does that even mean?” I asked.

“It doesn’t matter. You just want to be interesting and witty. Girls don’t want to understand you; they want to be intrigued by you.”

“I’d like to know what I’m saying, though,” I said as I grabbed my phone back and continued with the rest of the description for my Date Tonight profile.

The rest of the guys had left when our meeting was officially turned into my dating app help session, so Ren and I just continued to set up my profile. I didn’t buy into all the hype but really, what was there to lose. Ren seemed to believe his app had the ability to really help me find someone, and I was all for finding a nice girl. Or at least I thought I was ready to find a nice girl. It was hard to know since I felt like I had surrounded myself with crazy women recently.

Women were such beautiful creatures, and I really did appreciate all their qualities. From the women who wanted to work out all the time to the ones who hated to exercise at all. From the women who liked to party and drink on the weekends to the ones who stayed home and read good books; I understood all those decisions because I had felt that same way at one point or another in my life. But I wanted to find a woman that I wouldn’t want to let go of in the morning. It was a new urge for me, and I had to see if that sort of woman was even possible.

I had begun to think that my own one-night dating history was all there was out there. Guys that happened to find a wife and were having children and happy were an enigma to me, but I admired them very much. To watch their lives from the outside, it appeared they were much happier than I was.

I was happy. Sure, I wasn’t depressed about my life at all. I got to sleep with beautiful women and had an amazing job. But at some point, all of that even seemed old. At some point, I felt like every man wanted to find that one woman who they would grow old with.

“Okay, let me fill this out. I don’t want it not to sound like me,” I said as I started to fill out the rest of the questions.

“Just take your time. You won’t be able to get it all done tonight.”

“Why the hell not? How much is there to fill out?” My commitment issues had already started to rear their ugly head.

“There’s a lot, but it’s worth it. You’ll get questions that pop up throughout your user experience and answering them will help you find a better match. Always make sure you are answering the questions as honestly as possible. Don’t give the answer that you think is best; give your actual best answer.”

“Okay, but I don’t have time for an hour of questions every day.”

“It’s not that bad.” Ren laughed. “Maybe an hour of questions every other day.”

As I clicked through the barrage of questions, it became clear the app was trying to get to know me. It was asking everything that a date might ask, and I liked that concept. Instead of answering the same questions over and over again with blind dates, the app would hopefully use my answers to weed out people who just weren’t a good fit.

It took nearly an hour before my profile was filled out enough that I could see what matches were available to me. There was a sense of excitement in finding that I already had matches that were compatible with me based on what I had filled out that far. In New York, it sometimes felt like there were no women that were a good match, even though there were thousands of beautiful women.

“Wow, forty matches,” I said with pride as the number came up.

“That’s horrible,” Ren said and grabbed my phone. He played around with it for a minute and then gave it back to me. “These aren’t matches yet. They are women you can choose to match with.”

“Why is it horrible?”

“Go through and read these profiles and decide if you like them or not. Swipe right if you sort of like them. Swipe left if they are an absolutely no.”

“Hey, where did all my matches go? I’ve only got two left,” I said when I had finished swiping on the matches. “I swiped right on a lot more than two.”

“That’s all you need. Even if you swipe right, you don’t get matched with them until they also swipe right. And even then there are a lot of other algorithms that go into your matches. Your profile was set to match up with anyone who was an 80% match or more. I changed it to 95%. It’s not really worth playing the game unless you have a very strong match.”

I looked at the two profiles that were 95% matches, and they both looked good. Well, looked good on paper since I couldn’t actually see their photos. All the basics of what I was looking for were in the profiles, but they still didn’t seem like the best possible matches I could get. There had to be more.

“Can both of these women see that we are matched?”

“Yep, but you won’t be able to communicate directly yet. Women get the chance to say ‘yes’ or ‘no’ to a match before you can communicate with them.”

“So even though we are a ninety-five percent match, the woman might still decide not to match? Man this is getting confusing, Ren.”

“Don’t worry about all of that. Just keep answering questions, and go from there. There’s basically a different program for women than there is for men. The women don’t actually see the percentile matching system because research says they don’t like it as much as men. For right now, answer your questions that pop up, and tomorrow we can visit about the matches you get. You won’t get anyone over 95%, but you should get a couple that comes through at that rate. It’s New York; there’s millions of women, and you can’t be disgusting to all of them.” Ren laughed as he headed out.

“Thanks a lot. I’ll call you tomorrow.”

“Yep.”

I continued to click through the questions and didn’t see any other matches pop up. I could tell I was already losing my patience with this program. Only two matches; how the hell was I supposed to find a decent woman when I only had two options to choose from? It didn’t seem like the program was working all that well, but I continued with it for a little bit. By early afternoon, I was over the whole thing, though, and tucked my phone away. There was only so much online dating a guy could do before he needed to have a real woman by his side.

I loved women; there was no denying that. But I liked to have my choices. This dating app thought that by asking me questions, it could match me up, but I was a finicky character. Sometimes I liked a woman who was a little out of the ordinary for me. I liked blondes, but I had had plenty of fun with women of all hair colors, shapes, and sizes. The idea of pigeonholing me into one specific type wasn’t all that appealing. But I had to take a break from all the woman finding and deal with Merrick.

“Just because you own the company, doesn’t mean I won’t come over there and kick your ass,” I said when Merrick picked up the phone.

“Mom, is that you?” He laughed.

“Come on. You promised you were coming today.”

“Darling, I’m getting into the shower,” a woman’s voices said in the background.

“Hear that Wyatt? How could I leave such a wonderful woman all alone?”

“She’s not going to disappear if you had come to our meeting. She would have been there when you returned. No woman would dare disappoint you,” I joked.

Merrick liked to make his women happy; there was no doubt about it. He didn’t just want to have them for one night. He wanted to keep them for a couple of nights throughout the weekends, and sometimes even well into the next week. His typical one-night stand often lasted for weeks and turned into what I considered an actual relationship. Yet, when it was time to part ways, Merrick never seemed to have any trouble getting the women to let go. I admired his abilities in that aspect. I kept my dates to one night and still had to deal with some emotional awkwardness when it was time to cut things off.

“I’m coming over,” I said to Merrick, knowing he wasn’t going to like the idea.

“I’m not into threesomes with other guys, sorry.” He laughed. “Let’s just talk tomorrow at work. I have so many better options for spending my day today.”

“Let’s talk about the investment club. I need to straighten some things out.”

“Really, I should tell you to kiss my ass, but I know you’re not going to give up so just come over.”

Merrick knew me well. When I had something on my mind, it was difficult for me to focus on anything else until my item was figured out. It was like my brain preferred to focus on one item and get it totally solved before I could focus on the next thing. I had always been that way, and it served me very well in my business life.

I wasn’t the kind of boss who would say I’d get something done and then totally forget, being in middle management meant I had the owner Merrick to report to and that meant I had to get things done. I was focused and always finished each task. As much as other people thought my friendship with Merrick was why I had made it up the corporate ladder at our office, it was really because I could get things done, and of course, because I was a damn good investor.

I knocked firmly on the front door when I arrived. Just like clockwork, Merrick opened the door, and Bambi stood there, fully dressed and on her way out of his apartment. Merrick loved his women, but he was a businessman before all else and business always meant that his women only got half of him at any one time.

“I’ll send a car for you around eight o’clock,” Merrick said to Bambi as he kissed her passionately in front of me and then walked her to the elevator.

“See you later darling,” she said softly.

We waited for the elevator door to close, and then Merrick and I walked back into his place. It was not that unusual for him to say good-bye to a woman when I came over to visit, but it was a little weird how comfortable the two of them seemed already.

“So you liked this one?” I teased.

“She’s incredible. If I had been in Vegas, I would have married her.”

This was not at all like Merrick! Sure, he liked to keep a woman around for a little bit, but he absolutely never talked about marriage.

“That must have been one hell of a night,” I said with a laugh. “Maybe we will make an honest man of you after all.”

“We didn’t have sex.”

His statement took a moment to register in my brain. I had just watched a beautiful and very busty woman leave his apartment. They had clearly had a hell of a lot of chemistry by the looks of the kiss they exchanged. So the idea that he hadn’t slept with her didn’t seem like it was at all possible.

“Excuse me?” I questioned. “I heard her say she was getting into the shower.”

“We played Xbox all night.”

“What are you, twelve?” I laughed. “You stayed up late and played video games? I don’t know who you are or what you did with my friend, but I want him back.”

“It was the best time. She’s really smart. I threw some accounting questions by her about a new deal, and she was right on the money with them. She saw I had an old Xbox and wanted to play. So we played and had so much fun. It was like I was a teenager again.”

I just stood in awe and shook my head.

“So everyone was pissed off about you not being there this morning. You have to show up. I need everyone else to show up, so you have to.”

“Sorry, I’ll be there next week,” Merrick said in his typical response.

“Is there another day or time that would work better? The guys really do need your insights and teaching on this. As much as I have to admit it, you’re pretty damn good at your job.”

“No, next week will work. The day and time are fine; I just get busy sometimes. You know, it’s hard to pull myself away from a beautiful woman in the morning.”

This was the frustrating thing about trying to lead. I couldn’t imagine how frustrating it would be to lead a whole company since I was constantly frustrated with my small little investment group. But Merrick had a skilled team of leaders who worked for him. He didn’t have to lead most of the time; he only had to make sure the people he hired were doing a good job at leading their employees.

“What did you guys invest in this week?” he asked.

“We didn’t get around to it much. Ren ended up signing me up for his dating app, and I spent the whole time going through the questions.”

“Oh, yeah, how did that go?”

“Not really anywhere. I have two matches and spent several hours answering questions.”

“That’s great.”

Obviously, he wasn’t really listening to me if he thought two matches were a great amount of matches. But I was used to talking and having Merrick totally ignore me; that wasn’t something all that new to me.

“I only have two matches; how is that great?” I laughed.

“You only need one. From what I heard, Ren was really good, and the app made some serious love connections. His asset ratio when he sold the company was extremely high. I suspect it was one of those golden deals where both sides felt like they had hit the jackpot.”

“You know about his app?”

“Yeah, he was talking about it last month in our meeting. You know I actually pay attention when I come to the meeting. I’m not just a pretty face.”

“Well, still … two matches doesn’t seem like much. I’d like to have a little more to choose from.”

“That’s your problem right there!” he said accusingly.

“What’s my problem? That I want choices?”

“Yes. You are basically saying that even if your perfect match is handed to you on a silver platter, you still want to look around and see what’s out there. You’ll never find a good woman that way. You’ve got to enjoy what’s in front of you and stop worrying about what you’re missing.”

“I enjoy what is in front of me.”

“No, you don’t. It doesn’t matter how fucking amazing a woman is; you get rid of her after one night.”

“Not true. I’ve dated a couple of women.”

“Wyatt, get your head in the game here. You wouldn’t consider buying a stock and selling it one day later would you?”

“No, the market is too volatile, and it takes longer than that to get to know a company.”

“But it doesn’t take longer than one night to get to know a woman? Are you crazy! They are some of the most complicated creatures in the world. I’d say it takes at least three nights with a woman before I can make an informed decision on if I’d like to continue seeing her or not.”

I hated it when Merrick was right about things. Yet I knew that was exactly what I did. I always thought my perfect match was someone besides the woman I was with, so I never really invested in the woman I was with.

“Let’s be honest, not many of the women I’ve been with were really the sort to keep around.” I gave a laugh.

“How would you know?”

Merrick was serious and even stern in his expression. He was getting philosophical with me, and I always lost the argument when that happened.

“Because they weren’t. The women I have one-night stands with aren’t interested in anything more. They just want a quick release and to move on with their life when we are done.”

“You don’t know that, Wyatt. You wouldn’t know what a relationship even was. I’m your friend, and you know I love the ladies just as much as you do. But women need you to respect them. They get frustrated when you only pretend to respect them. If you only want a month-long relationship, be honest about it, and that’s it. If you only want a night-long relationship, don’t expect them to open up to you or anything like that. And you certainly can’t expect to ever find a lifelong partner if you’re treating her like a one-night stand. Even your perfect woman would run at that offer.”

“I don’t know why you’ve gotten so philosophical lately, but I don’t like it.”

“You know Bambi is one of the smartest women I’ve ever been out with. I had the best conversations with her last night, and I really can’t imagine another woman living up to that standard. I would never have guessed any of that by looking at her. I would never have known what a rounded woman she truly was if I hadn’t been willing to listen to her.”

“Okay,” I had no idea where he was going with this.

“So, I’m saying you need to get out of your uptight comfort zone and live a little. If Ren found out two matches on that system, then use them. Stop complaining and do something.”

“Okay, fine, I will!”

“Okay, good.”

“Wow, something’s come over you; that’s for sure,” I said.

“Let me see that app of yours. Let’s see those matches.”

We both looked at the two women I was matched up with, and as we were looking at the screen, a new match came through. It was exciting to have a new match; even though I understood the concept of fewer matches, I still wanted more choices, and I couldn’t help that.

“One hundred percent!” We said in unison.

“Her name’s Dakota; oh I like that,” Merrick said. “It doesn’t say that much about her, though. Blonde hair, green eyes, works in the arts. This really is a mysterious app.”

“Yeah, I have no idea why people like it so much. I had more information on my ninety-five percent matches than I have on this one.”

“It says they recommend you accept the match.”

“Fine, I accept it. I’d like to see this woman who is such a perfect match for me. Hopefully, I’ll get to see her picture now.”

It was true; I really did want to see who this woman was. Ren had said there wasn’t any better match than 95%, so the fact that I had a girl who 100% matched with me was beyond interesting.

This whole dating thing was moving along rather quickly, and I suddenly felt my chest tightening with apprehension. I thought I wanted a match, a woman that I felt really connected with, but now the prospect did seem very overwhelming to me. Would I even know what to do with a woman that was my actually perfect match?

“Okay, now I guess we wait and see what’s next.” Merrick laughed. “Maybe she will magically appear in your bed tonight?”

“Very funny.”

“Hey, I wouldn’t put it past Ren. He’s a billionaire you know. They are really smart.”

Merrick always joked like that. Because he was a billionaire, and people said things like that to him. They thought because he had money, then he could fix almost any problem. But they didn’t understand that every person was different, and we all had things that we were good or bad at; the amount of money in our bank account didn’t change our skills. Being rich didn’t make Merrick or Ren better people than they would have been if they were poor. Being rich just made it a little easier to be the best person they wanted to be.

***

Monday morning at work was always my least favorite. It took everyone too long to get back on track, and the markets were usually halfway through the day before my teams seemed to get a hold of their trades for the day. Trading was a science that used graphs and charts, but the role that the human trader played in the market was never more visible than on Monday mornings.

I loved money. I loved trading it and making it. The excitement of the trading floor had been my favorite as I learned the investing business, but it was exhausting and so stressful that I couldn’t stay doing it. There was an admiration from me to the guys who could keep doing the floor trading, though because I knew firsthand just how hard it could be. Floor trading was physically and mentally for the new and young traders. As I aged, I was able to learn that lesson and got myself into an office and off of the trading floor.

Mondays, just like all the other days of the week, went by quickly when the market was volatile. It was well after the closing bell before I was able to sit down at my desk and not feel like I was going to lose millions of dollars. Every day was similar to some extent, but Mondays were by far the worst.

When I finally opened my phone to look through the Date Tonight app, I still expected to see more matches than the three I had. Was I really that hard to match up with? Or maybe I was just expecting too much from an app developed by a teenager. Ren had only been 18-years-old when he came up with the idea for his dating app, was that old enough to know what people wanted in a love match? I wasn’t sure.

There was one unique thing about the girl I had a 100% match with; I now had the choice of some pre-selected starter conversation flirt messages. It seemed silly not just to allow full one-to-one conversations between us, but I was starting to realize this was a game and that the game was part of the appeal to people. I went along with it for fun and found the message that I thought best suited my personality.

---I’m excited to match with you. Should we move things to the next step?—

The truth was, I had no idea what the next step of the game was, but it seemed the only option that would move me closer to meeting this girl. There was no way I was going to fall for her until I saw her in person, so I just needed to play the game until that could happen.

I was about to close the app when I was notified that I received an answer. My adrenaline spiked at the realization she was online at the same time as me.

---Yes, should we play the game?---

Her message also seemed like a premade choice, and I couldn’t help wondering what her other options had been. What game? I thought. Weren’t we already playing the game? I clicked on her message, but this time, instead of giving me a long choice of options to reply to her, I was only given two options.

---Match with Dakota and Play the Game---

---UnMatch with Dakota---

Again, there was no real choice here. Of course, I clicked ‘Match with Dakota and Play the Game.’ I had to see who she was. I was so curious I could hardly wait to see what would happen next. But then my screen went black, and one message filled the screen. There was nothing to click on, no other options, just a black screen with the message in the middle.

---The Game Has Started---

I tried clicking back to the home screen. I tried to go back to Dakota’s profile, but I couldn’t go anywhere. Apparently, I had just started the game. I laughed to myself. Hopefully, it was a game that would end with me meeting this girl, and hopefully, she wouldn’t be hideous.

Dating apps and games weren’t at all interesting to me. But I felt excited at the prospect of getting to talk to this girl in real life. If she had gone through as much trouble as I had with all those questions and surveys, that meant that she obviously was interested in finding a match.

Dating in New York was hard. At least it was hard for me and most of the guys I knew. It was impossible to turn down a beautiful woman when you were at the bar, yet I always felt like there was another pretty woman that was even nicer who I might be missing.

Dating often left me feeling totally unproductive, and I didn’t like that feeling at all. I was used to making things happen at work, and I was looking forward to building my dating skills so I could make things happen in my dating life.