That One Time I Tried Online Dating: Part Two

Read part one here.

After typing in my credit card number for the required $15 membership fee, I uploaded my picture, typed in a few sentences for my profile page and filled out about 60 percent of the site's personality test.

Then....Then I didn't do a whole lot.

As I had learned during my first go-around on the dating site, I wasn't really interested in that many of the eligible men. There was actually only one man on the entire site that I thought was attractive. Some guy finishing his MBA at Ohio State. Seeing as that was hundreds of miles away, I didn't think that road was worth pursuing.

I checked the site every few days to see if there was anyone new or to respond to any "flirts" or messages sent my way. I exchanged a few messages with a guy named Sherman from Utah and a 51-year-old man invited me to take a midnight ride in his convertible. Both of those fizzled fast.

I was catching up with Margo one afternoon and telling her that the month was a total flop.

"There isn't anyone you're interested in?," she asked. I did a quick scan in my mind through the profiles I had seen.

"Nope, no one," I reported. "There was one cute guy in Ohio but, well, he's in Ohio."

Margo told me to message him and see what happens. I hesitated, but Margo and I basically came to the conclusion that I literally had nothing to lose at this point in my life.

Days later, I pulled up his profile and clicked "Message." I received a few messages during my month experiment, and let's just say there are very few ways to send an email to someone you've never met and let them know you're interested without sounding completely creepy.

So now with it being my turn to initiate a conversation, I knew I was attempting the impossible.

"A 51-year-old man is trying to date me. How's the site working out for you?"

A few days went by. No response. I figured that was that and looked forward to my move to New York City where I would more fully embrace dating.

Then one day, an email popped up in my inbox.

"Hi! Sorry it took me a while to reply. I had cancelled my subscription and was debating whether or not I should renew. I haven't had any cougar problems, but a 50-year-old woman is a lot less creepy than a 50-year-old man. Anyways, my name is Jared."

Jared. That's a name I now say and think about hundreds of times a day. But this, this was the first time.

He asked me about my life in Colorado. He told me about living in Columbus and missing the Utah mountains that he had grown accustomed to while he was going to college there. We talked about goals after school, our travel adventures, how I play a mean game of Scrabble, our families, my divorce, religion...Within a week, we were emailing several times a day and loving getting to know one another. I knew it would eventually fizzle out, seeing as we were so far apart, but it was just fun to have emails to look forward to.

Then one night, I was at Anthropologie returning something after having dinner with my parents. While the sales person was processing my refund, I pulled up my email on my phone to see another note from Jared.

"Hey, so I was looking at my itinerary for my trip to Salt Lake City next month and I have a layover in Denver. I am fairly certain that I can get a flight out of Salt Lake City a lot earlier in the day. Would you be interested in hanging out for half of the day? I thought it would be a good opportunity. If you don't want to, I understand."

I specifically remember feeling my face light up. My dad noticed too and asked what it was that I read. I quickly said something about getting a nice email from a friend. That wasn't a lie, right? It was technically a nice email from a friend. I actually kept Jared a secret for a while, except for a few girlfriends. I felt oddly protective of this new friendship and wanted to keep it safe.

It was not like me to do this. To email with some guy. To agree to meet him. Especially a guy like Jared. I had seen a few pictures of him and I felt like I was playing with someone way out of my league. I was just pretending the last few weeks. I couldn't possibly meet the guy...

Well, could I possibly meet the guy?

My girlfriend, Chelsey, was one of the few who knew about the emails. She asked me what I was going to do when I told her he wanted to meet.

"Well....I think I have to meet him."