This post is the second in a series of thirty stories from my life. For more info click here.
I had only been 29 for a few short weeks when I came to the conclusion that there was a very good chance that I would be single for the rest of my life. This wasn’t a sad realization for me, it was simply true and I was completely fine with this idea. It helped that the last few girls I had dated at that point were completely crazy.
I had decided to move on with my life and not worry about trying to find someone to love. If someone happened to come along, great. If not, that’s fine too. The bottom line was that I wasn’t going to put much effort in to that area of my life anymore. In fact, I had put so little effort into dating that the last two girls I went out with asked me out.
Then girl number three came along. I had been working out consistently at my company gym for a few months and was starting to get familiar with the staff members there. Dee was the manager of the facility and we would make small talk from time to time and I didn’t really think anything of it. I assumed that she was just being nice because that’s good customer service. However, one day she stopped me by the towel area and we chatted awkwardly for a little while and I began to suspect that the Fitness Lady might be interested.
Not too long after our awkward little conversation, I got a voice mail on my work phone. Dee had decided to invite me to the “singles” Valentine’s Day party that she and her friends were having. Now I knew that the Fitness Lady was interested. Unfortunately, I had a fundraising event for pH that very same night. I let Dee know that I wouldn’t be able to make it for the first part of the party but that I would try to stop by after the fundraising event.
When the night of the party rolled around, took care of all of my pH duties and then sent her a quick text asking if she was still at her party. She said that she was and that I should stop by. I hopped in a cab and made my way over to the bar. When I arrived, things seemed to be winding down and I couldn’t find her at first. Eventually, I spotted her and saw her sitting there looking adorable in a cute little skirt and white t-shirt with a big red heart on it. It was also the first time I had ever seen her with straight hair. She looked hot. We chatted for a little while and the bartenders started herding people out the door. As her friends grabbed a cab, we stood awkwardly on the sidewalk. As I was about to ask her if she wanted to go out some time she said, “So, are you going to ask me out?”
I was caught off guard and said, “Yeah, I was just about to do that.”
I finally asked her out and we agreed to work out the details later since her friends were yelling at her to get into the cab. We hugged and headed our separate ways.
We met again on the very next Wednesday (Feb. 16, 2005) for our first date. I decided to take her to Feast, which was right down the street from my place. I walked there and she had her roommate drop her off. I was there a little early and sat in the bar waiting for her to arrive. Once she got there, we took our seats and made a little small talk. We talked about our awkward conversation by the towels and all the poorly-worded emails I had sent her. She looked great. She was wearing a white sweater with pink and brown diamonds (not sure if it counted as argyle since it was only one row across the front) and a very flattering pair of jeans. I snapped a quick photo of her with my camera phone, but had to do it again when she wasn’t happy with the picture.
After our delicious meal and wonderful conversation (I don’t remember exactly what we talked about, but I do know that we laughed a lot) we walked south down Damen to North Avenue where I would hail her a cab home. We quickly found her a cab and before she got in we kissed goodbye. It was easily the best first kiss I’ve ever experienced. It’s probably the best first kiss anyone has ever experienced. She got into the cab and I turned and walked back towards my apartment feeling light and happy. I knew something good had just happened, I just didn’t know how good yet.