Best. Kiss. Ever.

Lips are made for kissing, particularly when they're finally the right lips

I've always thought of myself as a pretty good kisser.

Until recently.

A few months ago, I dated a woman whose company I very much enjoyed, but for some reason she and I were never able to lock lips quite right. She'd open her mouth too wide and I'd slobber on her chin and, in the confusion, we'd invariably knock teeth. It was like being back in junior high school without the braces.

We ultimately broke up because of it, as she informed me in an email kiss-off:

I was a bit unsure of the romantic connection all along and then it felt solidified over something as stupid as feeling I could never get the kiss right, it never merged or connected, which seems like a Seinfeld episode in the most pathetic way.

My amorous interludes were even more Costanza-like with two women I had dated briefly before her. One sucked in her lips so tightly that it looked like she was holding her breath until it was over (which it was, in a few seconds); the other simply refused to budge as I attempted to pry her mouth open with all the grace and subtlety of Gene Simmons.

I've always loved kissing, so much so that I hardly ever close my eyes. For better or worse, I need to see the look on the face of the woman I'm kissing. I'll often nudge her to open her eyes too, and when it's for better, the sparkle of fearless connection is just about the greatest turn on in the world. Now I know that I'm no Armie Hammer or Oscar Isaac or any of those good looking guys with a funny name, but I never really questioned my osculatory skills before. I use Kiehl's Lip Balm #1 every night, which I hope speaks volumes about how seriously I take this activity.

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In fact, my last steady girlfriend and I could've been the models for Rodin's or even Klimt's The Kiss (but not, thank God, Kathryn Harrison's). The first time we sucked face lasted close to eight hours. It happened on our second date and we were at the beach, and after a quick dip in the chilly water, I asked if I could kiss her. She said sure, I leaned in and things immediately began to heat up. The crashing waves provided the clichéd soundtrack while we were blissfully swept away. We were insatiable, and didn't care that near-naked people walking by our disheveled blanket were making fun of us. We kept kissing until dusk.

A few women have told me that I'm a great kisser and others have noted that I was more meh than mwah! I usually believed whoever I was with at the time. Of course, as every other online dating profile makes mention, physical attraction always boils down to chemistry. And that's as mysterious a thing as love itself. You can be wildly drawn to someone with Angelina Jolie–caliber lips and her kiss can feel like sucking on ice chips.

And then there's the converse. I once went out on a first date with a rather serious-looking criminal lawyer. We were drinking and at the end of the night, we launched into a marathon kissing session while waiting for the F train—which I realize sounds euphemistic in this context. We must've let a dozen of them roar by before finally releasing each other and coming up for air. Inexplicably, she and I never saw each other again.

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I must confess to one other junior high era impediment: Although I'm in my mid-fifties, the prospect of kissing a woman for the first time always brings me back to the first time I ever kissed a girl – Miss Laura Glass, in the library, with what she probably thought was a lead pipe. Shouldn't that adolescent anxiety have gone away by now? To be honest, I'm glad it hasn't. That thrilling, almost nauseating combination of anticipation mixed with dread is one of the wonderful things that keeps me young, although the flip side is that I still never know when to make my move. So I thought I'd consult an expert – and texted my younger son, Zach, who's a film major at a Florida university.

L: Can I ask you a question?

Z: Shoot.

L: It's about kissing.

Z: Uh-oh.

L: How do you know when it's the right time to kiss a girl?

Z: Honestly, Dad. I don't think I'm the right person to ask.

L: How come?

Z: Cuz it's not like I'm going out on dates.

L: Right, I know.

Z: It's just that I don't find myself in those situations.

L: I get it. College is different. But hypothetically speaking …

Z: And I'm more like the guy who misses the opportunity and winds up in the friend zone.

L: Like father, like son. Story of my life, man.

Z: It's like I'll be at a bar talking to a girl. For me, it's just talking.

L: For me, too. I know what you mean.

Z: And I'll notice how close she is to my face, and since I'm taller she may get a little closer …

L: Yep, that works. I'm also taller.

Z: And … I literally don't know how to put the rest into words.

L: Just keep going.

Z: Well, if we're both vibing each other, it just sorta happens.

L: Right, right! So here's my deal. I'll be out on a date and we're "vibing" …

Z: HA!

L: … and then it's the end of the night and things begin to get a little squirrely.

Z: I truly have no idea what you're talking about.

L: It's like, should I or shouldn't I?

Z: I don't know what to tell you, Dad. It's just one of those things I can't explain.

L: Me neither.

Full disclosure: The real reason I asked Zach about kissing was that I had gone out on a first date the prior Saturday and when the time came to make my move, I lost my nerve, and got a perfunctory peck-on-the-cheek consolation prize instead. But it was cool because I really liked her and knew I'd eventually have a second shot at our first kiss. As it happens, she lives just a few blocks away from me in the same Brooklyn neighborhood and we arranged to see each other soon.

On Monday, we began a lengthy email exchange filled with witty, semi-charming banter and made a plan to go out that Friday night. In one of my messages, I revealed my history of kissing apprehension, and lo and behold, she liked it! I believe her exact words were "You're making me crazy." To which I responded "Good!" She then sent me another email that said, "By the way, you should." And I immediately responded with, "I fully intend to." And then we exchanged some flirtier missives that made us both smile, to say nothing of the lingering feeling that we were in a John Hughes movie.

And maybe we were: Right after this flurry of emails, I went to the local Rite-Aid because I was out of tall kitchen garbage bags and diet ice tea (I am the George Clooney of Park Slope). Then, while I was standing on line at the checkout, guess who walked in?

That's right.

She looked at me and I looked at her and it felt like we were inside of each other's dream. Just a few minutes earlier, we had been plotting the logistics of our first kiss, and here we were, without prior warning, face to face, and I hadn't even brushed my teeth.

"This is so crazy," she said and started to nervously laugh.

"I think we should kiss right here," I said with a relaxed confidence I didn't know I had until I heard my own words.

"I have stage fright," she admitted and looked away, her pale Irish face shyly reddening.

"So do I!" I said. "I think everyone does."

"I'm actually here to buy toilet paper," she said. "Sexy, right?"

"Tell you what," I said. "Let me check out and I'll come find you."

She was shopping in the back, near the greeting cards, and her beautiful face was still glowing bright red. "Do you think they have birthday candles?" she asked.

"I don't know," I said, "but let's kiss."

And so we did. Right next to the half-price Christmas ornaments and Dark and Lovely hair-care products, under the now strangely romantic fluorescent Rite-Aid lights, we kissed and then paused for a moment to fearlessly look into each other's eyes and then gently kissed again and began to breath heavily, drunk with excitement, and then paused to smile at each other and then sweetly, tenderly, sloppily kissed one more time until someone on the store intercom ordered a cleanup on aisle Larry.

Best. Kiss. Ever.

Tags: dating