Jumping Into The Water

"How are you almost 25 years old, in 2015, and you haven't tried online dating?" Shelby asked, more stunned than annoyed. "And how," she continued, "have you worked here and not thought to try out the product."

I shrugged as I picked at my boring turkey sandwich in the cafeteria. "I was dating Scott for almost a year. And before that, I had thought about it, but I don't know." I really didn't have a good answer other than never two it wanting to put myself out there. "Isn't it kind of scary?" I asked.

Shelby frantically shook her head. "Not at all," she replied. "It's kind of exciting. I thrive on the rush." I never realized that Shelby was such a fan of online dating, but apparently it was her main source of social entertainment. "Promise me that you'll try it at least once."

I slowly nodded, still hesitant. "Okay, I'll definitely give it a try."

When I told Anna about my new challenge over the phone later that day, she practically screamed with excitement. "I always told you to try it!"

I rolled my eyes, even though she clearly couldn't see me. "Yeah, but I was with Scott. Plus, you only boned guys from Tinder. I wouldn't classify you as an online 'dater.'"

"Once you realize that there's no stigma anymore, you'll totally love it," she continued. "Plus, I met Charlie on Tinder, so I still got to the same end point. I just had a lot more fun along the way."

I nodded to myself. "Maybe I just need to screw a bunch of guys until one is dumb enough to date me," I joked. "And I don't think there's a stigma," I elaborated. "Peggy made the same comment to me. I think it's great that people date online and I wish I was more comfortable with it, but it makes me so nervous."

"Why?" Anna asked.

"At least when I meet a guy in a bar or through mutual friends, I get a feel for his presence. I know right away if he's awkward and what he actually looks like. What if I meet a guy from online and he's strange or I'm simply uncomfortable around him?"

Anna laughed. "Then you tried and you'll have a great story!"

Anna's words comforted me and while I didn't tell Shelby that it was actually Anna who convinced me to take the plunge, I don't think I would've had the guts if Anna's last statement wasn't replaying in my head.

So, with the help of Shelby and Peggy, I made my first dating profile. I didn't want to fill out the information, but they insisted. "Hello, you fucking work here," Shelby said quietly over my shoulder as I sat at my computer pouting. "You should know better than anybody that the more full profiles get more traffic."

It was true. Not only did I know that tidbit of information, but I was constantly going over information about what made certain individuals more successful at online dating than others. I also spent a lot of time talking to men and women about what they were looking for in a partner. I had this incredible advantage, but why was it so hard to use this knowledge for my own personal happiness?

So I schedule a date. He works as a high school teacher in a neighborhood right outside Santa Monica. We quickly bonded over a mutual love for Harry Potter and within a few exchanges, he asked if I'd be interested in meeting. I was hesitant, figuring that simply talking to guys online was a comfortable dipping of my toe in the pool, but I knew I had to eventually take the plunge. Why not just jump right in without stressing about it?

I agreed to meet him on a Thursday around 4 for coffee. I kind of wished we were meeting for an actual drink, but this meeting was perfect. I told him that I had to go back to work after our meeting, so I had an easy out if the date was a bust.

I arrived at the coffee shop two minutes ahead of schedule. I saw him sitting down, looking at his phone, and before I even had my hand on the door, he looked up. We made eye contact and I tried my hardest to give him a genuine, care free smile. On the inside, I was freaking out.

"Hey," I said when I walked in. He mimicked the word back to me as we mutually went in for a friendly hug. This was one of the things I wasn't sure about the etiquette on. I had asked Anna earlier in the day how I should greet him. He was essentially a stranger, but a stranger that I had been flirting with for almost a week now. She assured me that it wouldn't be awkward and, so far, it wasn't.

He had ordered me a coffee and I thanked him for it. We began to make small talk as I went to pick up my coffee cup. My hand was shaking so much and I prayed he didn't notice. Why was I so nervous? It was a simple date.

We talked about our jobs and past schooling a bit; nothing too deep, but it was nice to sit down in person with him so I could get a feel for who he actually was, besides a expressionless conversation partner on my computer screen.

It was nice and our conversation seemed to flow relatively well. After about 50 minutes, the alarm I set went off and I told him that I unfortunately had to head back to work.

"It was really nice to meet you, Caroline," he said to me with a hug outside the coffee shop as we went our separate ways.

I agreed and the date was over. I didn't think my heart could speed up any faster, until I looked down at my phone.