I had a long walk back to the light rail station from Grace’s house in early December.

After a fresh and heavy snowfall in this mid-tier American city, I had to traverse a lot of sidewalks that were halfheartedly shoveled, or shoveled not at all. The still air and inconsistent street lighting would usually make a walk at this time of night in this part of town eerie, but my step was uptempo and my spirits were buoyant. When I got on the empty train home, I stood gripping a pole and felt like dancing; I smiled like I’d found Jesus.

Grace and I met up at a hip little joint on the south side. I got there first, even though I was late myself, and when she walked in the door she was every bit as cute as her photos on OkCupid suggested she would be. Her subtle smile she flashed me when I flagged her down told me that she thought I wasn’t half bad looking myself.

Conversation flowed effortlessly for the next three or four hours. She was a recent grad from a nearby liberal arts college who wants to be a doctor and she had the MCAT scores to do it. We found out we did the same dorky activity in high school. We talked politics, religion, swapped stories from the developing country we’d both spent serious time in. I kept her laughing at the stories I told. When I leaned in to the table to be closer to her, she leaned in closer for whatever reason she felt like leaning in closer. I told her she was my first date off the website, and she said I was only her second – and she’d been on there for 8 months.

I’d been on the site for a week.

Flash back some pages on the calendar..

The ex was dropping me off after she had made her feelings clear. I sat in mostly stunned silence as I began the arduous journey of trying to process what the fuck had happened to make the woman I thought I could spend my life with decide she wanted out. When the car stopped, I patted her leg lightly to say goodbye and reached for the door handle.

It was oppressively sunny. My sunglasses came off but hers stayed on. They didn’t catch the tear or two she was shedding; I don’t think this was easy for her either. My naked eyes didn’t conceal any emotion.

She said a pat on the leg was a miserable way to wrap this up and she embraced me with both of her arms. I hugged her tightly too, despite the pain and humiliation I felt. I stammered something stupid about how I shouldn’t feel sad for what I’m losing but should appreciate what I had gotten when I had it – blah, blah, blah. She gave me a surprisingly tender kiss on the forehead, I said goodbye, and I stepped out of the car and out of her life.

The trauma of that day receded into the background as the tap beers flowed that night in December with Grace. This gal was unbelievably cute, had a lot to say, and was doing great work with a non-profit. And she was in the bar with me.

While browsing the singles on OkCupid she’d stood out by virtue of her unreasonably attractive photo. (When I showed the horny old men at the office, their eyes bulged) I scanned her profile, whipped up a couple inane things to message her about, and sent them off. In her reply she said she wanted to skip the internet chit chat and just get together soon; she stressed she wasn’t a serial killer.

I wouldn’t have been super concerned if she were.

As the night wrapped up I offered to walk her back to her place nearby and off we went. When we arrived, she gave me a big hug and we both said we had a lot of fun. I walked off into the night thinking filling the gaping void my ex left wouldn’t be so hard after all.

Of course, if things with Grace had ended up happily ever after there wouldn’t be much great material for one guy’s blog about online dating in the 2010s, would there?

After 31 dates (and counting) with 19 women over three months, I’ve learned a lot. I’ve got some good things going for me, but I’m no model and I’m not a born player. I’ve been fortunate enough to be involved with a series of inspiring, brilliant, and beautiful women – and insomuch as I can help others find love, I’m going to share what I know on this blog.

Follow along on my journey as I try to get back to having merely 99 problems.