I recently celebrated a “pre-milestone” sort of birthday: 29. Compared to 16 and 18 and 21, 29 feels like a big number, a big age, an age one might even ascribe as “old.” But I’m giving myself permission to live especially youthfully this year — my last year as a twenty-something. I’m looking forward to lots of hikes, waterfalls, and cookies-and-cream milkshakes in these twelve months ahead.

I’ve learned a lot about personality models in these latter years of my twenties, particularly the Enneagram. As an Enneagram Type 4, I’m more prone than others to look back on my past and lament the holes and gaps and unfulfilled longings. Turning 29 is causing me to look back on my childhood, adolescence, and even this last decade of my twenties.

Among myriad other losses I could mourn about, I’m fixated on the one where I’m almost 30 and I’ve never been kissed.

You’d think I’d have had that little life experience by now. Hasn’t everyone? A girl on the playground or on her doorstep; even a boy from the Internet or some other promiscuous outlet for my same-sex lust.

Alas. I’m almost 30, and I still haven’t experienced my first kiss. Never been in a single romantic relationship. A “true virgin” if there ever were one.

My lack of a first kiss is the ultimate “Never Have I Ever,” and yet never have I ever shared that fact when playing said game with others. It’s just too shameful.

Unless you too have never been kissed, I cannot quite put this cloudy feeling into words. This heavy mist of “missing out.” This encircling void beyond “normal” boyhood — or at the very least young adulthood.

I’m currently reading The Perks of Being a Wallflower for the first time, a personal favorite of one of our blogging brothers. I was especially pricked by something that female love interest Sam said to our innocent teenage protagonist, Charlie. Sam is a few years older than Charlie, and she has repeatedly told him that she doesn’t want him to think of her “that way.”

But then Sam drops this line on him:

I want to make sure that the first person you kiss loves you. Okay?

He says, “Okay.”

And then she kisses him.

Oh man.

The feels on that one.

I look back on my life and wonder why this whole matter of a first kiss has never eclipsed after nearly three decades. Are people — girls, guys — really that repelled by me?

Is something wrong with me?

But before I pour on the self-pity, let me say this: I’m really glad my first kiss hasn’t come from some girl in middle school who now means nothing to me a decade and a half later or especially a random dude from the Internet.

You see, that’s the thing: I don’t really mourn my lack of a kiss for the physical kiss itself. I mean, I want the kiss a little. But what I really want is the belonging amid a twenty-something society full of first-kiss’ers.

As an Enneagram Type 4, my core tells me that I am so very different from the rest of the human race. And this feeling of separation applies to just about every facet of my life:

I’m a Christian — oh, but I’m attracted to other men.

I’m a man — oh, but I’m sensitive and crave quality time and physical touch with dudes daily.

I’m a single twenty-something — oh, but I’m still a virgin and have never dated and never even been kissed.

Even among the guys in this “SSA Christian” community, I don’t feel I quite fit into the same box. I haven’t “done stuff” that other guys here have done (kissing included), I don’t share many common musical or film tastes, and I actually kinda sorta like and even love sports — both the watching and the playing.

Going back to the kissing thing, though, it’s a haunting thought: wondering who, if anyone, will be my first kiss.

I mean, can I go to my grave and still feel like I’ve actually truly lived without a first kiss to my lips?

Though I’ve never been kissed, someone did try to kiss me once. I don’t want to divulge the full story just yet, but looking back on that moment, it has always fascinated me that my first instincts had me not accepting this advance.

I actually turned my face away as this person’s lips started to lunge inward.

I didn’t even have to think about it.

I still wanted the experience of a first kiss then, just as I want it today.

This person was quite attractive and nice and funny and fit and into sports and a Christian.

And I did not want my first kiss from him — a man.

For how desperately I’ve often wanted to be kissed, I’ve also always wanted my first kiss to be the “right” first kiss.

Maybe this desire stems from my standing as a writer and my affinity for good stories. As much as my having never been kissed burdens me the closer I inch and sprint to 30, I’m grateful not to have “wasted” such a special moment as my first kiss. You know?

I guess I just don’t want any more holes or regrets than I already hold to my name.

God knows I’ve already got plenty of those.

Who did you share your first kiss with? Or, like me, have you also never been kissed? Do you ever feel like you’re “missing out” on the human experience — for better or worse?

* Photo courtesy winterpeen, Creative Commons.

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