I’d met Kym nearly 10 years earlier; she was a DBA in my department, and part of the social tech nerd crew. She was smart, funny, and vivacious, but we were both with other people, and you know what they say about dating at work.

I never forgot her, though, and after a decade that included a shift from corporate to entrepreneur, a painful divorce, and the budding realization that I wasn’t very good at dating, I was completely shocked one day to see her name show up in my “Recommended Friends” list on Facebook (remember that?). I had asked around for her a few times since becoming single, but no one ever had any news, so I was completely flabbergasted and wondered who we shared as mutual friends.

As it turns out, pretty much everyone.

I sent her a friend request, and held my breath until she accepted (fortunately, this didn’t take long). And then, just to be sure for myself:

Four agonizing days went by with no response, until:

“So good to hear from you!”

“So good to hear from you!”

“So good to hear from you!”

Had she thought about me too? I ran through the “catch up” rituals, and tentatively asked if she wanted to get together sometime soon. She said yes.

And then, I panicked.

I had absolutely zero adult dating experience. My first “real” relationship started in my late teens and lasted until 30. My second was an evolution of a friendship. Between the two, I’d gotten to 34 without ever having gone on a first date.

We scheduled for Sunday, since I was going out of town for the weekend, and wouldn’t be back until Sunday morning. Friday evening, as I hung out with friends in Tampa, I learned where all the connections were. Two of my very best friends (Hey Mandie, Hey Oksana!) knew her through former co-workers who’d gone on to work at the company where she was. When I admitted my predicament, dating pro Oksana gave me the run down:

– Pick your first spot somewhere neutral, that serves alcohol. I like shooting pool, so a pool hall was agreed to be a good spot.

– If it seems to be going well, but your time there is wrapping up, ask her if she wants to go to a second location, somewhere more intimate. If she says yes, that means things are going well. I had a favorite watering hole which hosted Poker tournaments and Karaoke, and had the added benefit of dim, cozy booths. Perfect. Plan is ready.

I confirmed meeting up at the pool hall with her, and prepared like a Junior High Schooler, with butterflies in my stomach. I cabbed it to the pool hall a little early, scoped out a corner table, and started running a few racks to burn off the nervous energy. I got a text around the appointed time that she thought she was there, and went out to the parking lot to meet her.

She was gorgeous, exactly as I remembered her.

We played a dozen racks, laughing, sharing a pitcher of beer and tech stories, catching up on life in general. When our table time began winding down, I remember O’s advice, and steeled my nerve to ask: “Want to go to this cool bar I know?”

She said yes. Things were going well! I silently high-fived myself, and we headed down to the Banana Boat. We started off by both entering the Poker Tournament; she went out in the first round, and feeling bad for leaving her on the sidelines, I played to lose. Just as my chips were getting low, she got in a second round on consolation (it’s a Poker thing, look it up). Now she was playing, and I was down to low chips on the table, fighting to stay in. I managed to squeak back up to a very respectable second place finish, lasting only a few minutes longer than when she went out the second time. At this point, I was feeling like a champion.

We headed out to the main area to sign up for karaoke, and use the free drink coupons I’d won for my 2nd place finish. One pitcher had become three, and our conversation became deeper: what we wanted, what we missed, what we yearned for, the lessons life had taught us. We shared and commiserated, and when the bar announced last call, we were floored at where the time had gone.

It was a foregone conclusion we’d head to the diner next door for coffee and breakfast. I tried to stretch the minutes, knowing that the evening was drawing to a close. We ate slowly, had several coffees, and reveled in each other’s company.

Finally, she dropped me off at my sister’s, where I was crashing for the night since it was close to the area, and I had moved to Clearwater. When she pulled in, she parked, and got out to give me a hug. I held it a second longer, then looked her in the eyes, and asked “Is it OK if I do this?”…

…and kissed her.

I have never in my life been considered a smooth man, but that night, for one glorious second, I was Fonzie, Rhett Butler, and Casanova all rolled into one. As I walked away towards the house, I looked back to see her cheeks red and mouth open. I silently fist pumped Breakfast Club style, and sailed into the house on Cloud 9.

The next evening, she came over for dinner. The rest was history.