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.