L.A. Affairs

His conversation skills are up for discussion

How to maintain conversation on a first date: He was doing something wrong

I entered the online dating scene about five years ago when I lived in Washington, D.C. A heavy travel schedule was limiting my meet-and-mingle time with local women, and the ability to line up a date online while waiting to board a flight solved that. But after dozens of dates that did not yield a real relationship, I began to wonder if online dating stopped at that — just dating. Or maybe, with all the choices in a big city, it was easy to dismiss someone if the first date wasn't a home run.

When I moved from Washington to Venice, I soon discovered the online dating profiles of Angelenos were different than back East. It took me about two scrolls to notice more tans, blond hair and descriptions filled with words like "spirited," "creative" and "yoga." And it took about three ignored messages to notice I had more competition. Fair enough, but I developed this foreboding sense that meeting someone in L.A. was going to be much more challenging than I had imagined.

After a couple of weeks, my first online date was with a cute late-twentysomething who actually messaged me first. I suggested we meet at the Phoenix. After ordering our drinks, we soon enough started working our way through what had become my standard set of first-online-date questions, such as:

Are you a veteran of the L.A. dating scene? Share your story

So tell me about your job.

Where are you from?

Do you have any siblings?

How do you like online dating?

While sitting at the low-lit bar, there was plenty of smiling and direct eye contact. We both beamed while talking about being an aunt/uncle. But after we finished our second drink, the conversation stalled. We began referring back to previous topics, but it felt forced. She got fidgety, I asked for the check, and within minutes we had called it a night.

On the way home, I replayed the evening over and over in my head. We had a lot in common, and I couldn't recall any major misinterpretations of something the other said. I was at a loss.

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This starting off high, ending low meet-up experience repeated itself several times over the next four or five months until I met Cailin. She was from Dublin and gorgeous. Our messages had that cat-and-mouse tone that guys find irresistible, so it was all I could do not to jump the gun.

When we did meet up, I suggested my standby, the Phoenix. The bartender came to take our drink order, and I motioned to her to go first. She looked at the menu and I sensed indecisiveness. So I said, "What do you like, wine, beer, the harder stuff?"

"Oh, I never drink beer. What about gin?" An odd question, I thought, especially since (a) she seemed old enough to have tasted gin before and (b) she would be the judge, not me.

"Well, it can be," I responded. "Want something refreshing? Do you like lime?"

"Yes," she confirmed.

OK, we were on the right track. The bartender offered to take it from there, but I recommended she make the cocktail with Hendrick's to add that subtle cucumber flavor.

While we waited for our drinks, Cailin smiled and said, "You seem to know a bit about drinks. How many different types of gin are there?"

She wanted to know about various high-end gins and vodkas, different wine varietals, what "Brut" and "Sec" mean on champagne bottles. At one point I became self-conscious that I knew too much about drinking properly, so I weaved in my brief experience as a waiter to dismiss any red flags that I could be a professional alcoholic.

Our conversation was fun and engaging, and she was enthralled. And though I was tempted, I resisted diverting the topic to ask one of the standard get-to-know-you questions.

Finally, after the first real lull in the conversation, I asked Cailin about her line of questioning. She said she had just been hired at a high-end Beverly Hills bar — her first time in any server-related position, ever. Without trying to offend, I asked how she landed that gig without any serving experience. She admitted she had great rapport with the hiring manager/trainer, who told her she was "going with her gut" when making her the offer. Sláinte to that.

After that first stage of conversation, everything came more naturally. We started the date discussing a random but mutually interesting topic that I give her 100% credit for initiating and me 100% credit for not screwing it up.

Unfortunately, Cailin moved back to Dublin at the end of the summer, and after doing "the long distance thing" for a year we recently decided to pack it in.

But I'll never forget the epiphany I had after that first date: Drop the standard Q& A routine and let things flow naturally. From now on those initial questions are treated like valuable vacation days: to be used in chunks to create an experience greater than their parts. Now I just need to take a full-on sabbatical in Ireland ….

James Short is a digital media executive living in Venice.

L.A. Affairs chronicles dating in and around Los Angeles. If you have comments or a true story to tell, write us at home@latimes.com.

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