Did it go well?

I really didn’t know. It had been more than 10 years since I had been on a first date. I replayed the night over and over in my head.

I liked how he asked what I thought about his outfit, how he pulled out my chair at dinner and how he asked the waitress about my gluten-free options. I liked how our conversation ranged from sports and movies to religion. I liked how much he talked and that he carried the conversation with humor and thoughtful questions.

Underlying the details was the fact that I had fun. From what I could tell, he did too. It seemed like a perfect first date and at the same time perfect practice for future dates.

It wasn’t until he asked me out again that my perception was confirmed: it went well enough to at least initiate a second date.

Date No. 2 was at a cute little authentic Mexican restaurant.

I looked forward to seeing him but didn’t know protocol for second date-behavior, especially since we’d already kissed. For example, how should I greet him? How will he greet me? (I opted for the hug and was relieved when he one-upped me with a kiss on the cheek.) Since we’d already covered a lot of getting-to-know-you basics in the first date, how would it go in the second? (Luckily the conversation was similar, but with more depth and room for teasing and the beginning of inside jokes.) If we shared one little kiss as we said goodbye the first night, should I expect the same tonight? (TBD.)

After sharing street tacos and margaritas we walked to a nearby bar for drinks and discussed playing a round of darts.

Dating, I’m learning, introduces pressure to participate in activities such as darts, pool and bowling; games I had successfully avoided playing for years. Spectating proved to be the best way to cope with my intensely competitive nature in the past, but I realized quickly this approach would no longer be acceptable as I began dating again.

Embracing my new “I can do this” mantra, I agreed to play.

My date seemed proud to be the dart expert. After a few wild warm-up shots I realized the opportunity for physical interaction would increase as he taught me proper form. For the first time in my life I was genuinely enjoying darts.

After the game we retired to a booth. His request that we sit on the same side made it easier for him to wrap his arms around me and steal a kiss. (Apparently I could expect more than a goodbye kiss tonight.)

I was appreciating our closeness and the smell of his cologne until he reminded me of my promise to explain my annulment.

Once again, I pulled my prepared response out of my back pocket. I was relieved as I watched him nod his head listening to my life story of marrying a pathological liar. I explained a few examples of my former husband’s fraud, then ended with an “it is what it is” comment, another mantra I had recently adopted. This statement seemed to sufficiently wrap up the story and he rubbed my hand in acceptance before kissing me again.

When we went to pay and leave the bartender commented on how cute we were and asked how long we had been together. I smiled in response and realized that if we hadn’t been the only people in the bar I would have been embarrassed for being “that” couple.

He wrapped his arms around me as we walked to my car, then he pulled me closer. I could taste his lips as we kissed again. And again. And again.

We decided to climb into my front seat to avoid the glances of people walking by on the street. Once there, I offered to drive him to his car.

I was intoxicated with his smell, and reveling in the way that my skin was still tingling where he had touched me. I was thinking about how he had run his fingers through my hair while stalwartly wrapping his arm around my waist. Cliché as it may be, I felt high when I was with him. Now I had to put all of that aside to focus on driving.

Internal dialog:

Focus! (his hand is on my thigh!)

Pay attention to the road! (now it’s running through my hair!)

Easy! (just inches from his soft lips!)

Focus!

As I pulled into the open parking spot behind his car an odd sound resonated in my vehicle. At first it was soft but then increased decibels until it was impossible to ignore.

I looked over at him and in that instant recognized it as a muffled rubbing sound.

Perhaps a scraping.

Perhaps a scraping of my car, against the car that I had just maneuvered to pull in front of…

“Did I just hit that car?” I blurted out.

The last time I was on a date my biggest concern was whether or not to use my fake ID to order a bottle of wine. I was a 20-year-old college sophomore who, at the time, had been on maybe a handful of dates. Soon after I started spending time with a guy friend of a friend, fell in love and eventually married. As the story goes, I successfully bypassed the dating world to settle into my Happily Ever After.

I would be confronted by my naivety of fairy tale endings several years later when my marriage fell apart and I found myself unexpectedly back in the dating world. Single again and nearly 30, I realized that my knowledge of dating is no more extensive than when I was 20 and struggling with whether to use my fake ID.

Saying that I am novice is a painful understatement.

But alas, here I am. Single. Embarking on the world of dating.

I met the man that would end up taking me on my first date at a karaoke bar downtown. He had just won a rock-paper-scissors match with a drunken bride-to-be, but had forfeited the match prize (an open barstool) when he realized that she wasn’t sober enough to stand. (See ladies, chivalry isn’t dead.)

I was in line to buy a drink, had the pleasure of observing the entire situation and in seeing me laugh, he struck up a conversation. He was handsome, funny, and had a bit of a nervous laugh that I found incredibly endearing. I committed to spending the rest of the evening dancing and chatting with him after he offered to serenade me Celine Dion and Enrique Iglesias.

As the night came to a close he asked for my number and a kiss. The number I shared, the kiss I denied, and three days later we had dinner plans at a nice restaurant across town.

Touching up my make-up and changing into my heels at my office, I prepared for the night.

I was nervous. I was excited.

Slightly relieved that we already breeched the dreaded “how are you still single?” question while grooving on the dance floor, I thought I was safe from having to go into too much detail about my recent singlization. Although I was concerned about sharing the details of my past relationship and possibly saying too much, more so I was worried about talking timeframes. I am an “If you fall, get back on the horse” kind of girl who doesn’t see the point of waiting around to meet someone new, but it had only been two weeks since my annulment was finalized.

I prepared a canned response in case the topic came up, settling on, “I was married, but am not anymore… I had my marriage annulled … if you wouldn’t mind, is it OK if we wait to talk about next time?”

Since I had already shared this information on the night we met (which his friend used to equate to me being like Britney Spears) I thought I might get away with it. Honestly, it was the best I could come up with to bow out of the question gracefully. I wasn’t saying I wouldn’t talk about it, but just that maybe I didn’t see the point unless we are going to keep seeing each other.

I realized in execution that my plan lacked depth. I hadn’t considered how he would respond, and wasn’t expecting the “That’s fine, but just know that my mind is racing right now.”

Had I made it worse by not just telling the story upfront? Would it have been better to go with Plan B: the full disclosure? I made a mental note: Rethink this approach in the future.

I didn’t have to worry about this too long as I would soon find out; most people have skeletons in their closet. He quickly shared that he, too, had a few questions he hoped wouldn’t need to be revisited, which included his age, profession, and living situation. He was a 24-year-old service manager for an automotive company.

And he lived with his parents.

Because he too wasn’t perfect and wasn’t necessarily someone I could see myself with in the long term (not that I was even thinking about the long term) my only expectation was that we would have fun and enjoy our time together.

Which made this date perfect practice for future first dates.

Luckily, we hit these somewhat uncomfortable topics within the first few minutes of happy hour and then were able to enjoy the rest of what ended up being seven hours together. Conversation was punctuated with witty banter and as he walked me to my car and we made plans to see each other again I was pleasantly reminded of an aspect of dating I had forgotten:

The first kiss.