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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  • Wow, Tom! That blows me away! Almost 30 and never been kissed!? Wow! I can understand 16 and never been kissed, but 29 going on 30!? That’s so amazing! But you know what? It tells me so much about you and the sort of guy you are. It increases my admiration and respect for you even more. You are one amazing, unique and special man. Thank you for being you. I want to say too, I bet Jesus was never kissed either! So you in such good company, bro! Know that, and know that kiss or no kiss, you are a really great guy.
    My first kiss? I was thinking about that as I read your post and I’m not sure I can even say. But I think back on my wife and our relationship and I know our kisses were special, but for us both it was not a first kiss, though it was perhaps a first kiss of love. I’m not really a hugger or a kisser, so I don’t really think too much about the actual kiss. But for relationship, companionship, being special to someone else and having that special person in ones life. That’s what I find important and what I always want and crave for. I can see how a kiss can symbolize that.
    Enjoy this last year of the 20s. Have fun! And don’t give too much thought to that kiss.

      • Sarcasm alert.
        So you’ll make 29 a special year, because once you turn 30 it’s all over: no more hikes, waterfalls, and cookies-and-cream milkshakes for you, old man. What real difference in the world does it make whether your first kiss comes a month before you turn 30 or a day after (or two years after)?
        Our parents inadvertently teach us that birthdays matter by giving us presents and parties. We do develop rapidly through childhood and adolescence, so there is something to it then. But even in those years, some people grow and mature faster than others, so about the only thing that age means is what year of school we’re in. All the more, when we’re adults, there is nothing inherently different between being 30 and being 29 or 31. People’s fixation on birthdays, especially the multiples of 10, as if they mattered, is, IMO, a foolish element in our culture. Stop falling for the foolishness.
        I wonder if lurking in the background is an even worse piece of our culture: the conviction that everybody is entitled to have, even obligated to attain, sexual fulfillment. We are expected (in the sense that otherwise we’ve failed) to have sex. Our culture tells us that we should have sex, as often as we can. Now, I know you don’t believe that, but it’s part of the culture we absorb. For you, it sounds as if that kiss is the functional equivalent of a sexual encounter. Put the obligation to kiss together with the birthday fallacy and, voila: the prospective tragedy of being unkissed at 30.
        I’m not saying this to be harsh, but I see two problems with your thinking as you do. One is that you make yourself needlessly unhappy by imagining that you are missing out on something that should be yours. The other is the possibility that you’ll actually do something you otherwise wouldn’t just to avoid hitting 30 unkissed.
        You ask, “I mean, can I go to my grave and still feel like I’ve actually truly lived without a first kiss to my lips?” Of course you can, if you allow yourself. It’s only the fallacy of our culture around sex that suggests you can’t. At 73, I’ve never been kissed, other than by my mother when I was a schoolboy, and maybe by my prom date in high school. I imagine that if I ever developed a close friendship with another guy, kissing and hugging would be a natural expression of our affection. But for me, it needn’t be exclusive. There are several people I know via the internet for whom I feel deeply enough that I’d be willing to kiss them. Beyond that, I’d say you’ve “truly lived” in the way we should want to, when you’ve given yourself to others in some meaningful way, as you are doing in your present job.
        It seems to me that you actually realize that what you really want is not so much a kiss itself as the sort of intimate friendship which could be the context for a kiss. This makes sense, but it’s not something that you can force. It’s something that can develop.
        So my prayer is that you’ll find close and lasting friendships and learn to stop obsessing over calendar age. God bless you.

  • Tom, thanks so much for the openness of who you see yourself to be: – a type 4 – a man with holes and gaps and unfulfilled longings. I’ve never taken that test but I have taken others and I always end up heavy on the melancholy spectrum, which sound very much like your #4.
    You don’t know me that well, yet, and I hope I am not perceived as trying to fix you (I have that tendency) but I do know about the regret of unfulfilled longings. Now 54 years of it.
    Back when I about the age you are now (that really sounds so father like) I was lamenting over the holes and gaps in my life at that time. While I was reading Proverbs 3:5-6 – the Lord took the time to start the process of showing me just how big He was and in control over my life – even the holes. :0)
    In short – He showed me that the promise of making my path straight was not limited to just the future – since he He isn’t limited that way. That as I learned to acknowledge Him – pursue knowing Him every day and not rest to much on how I see myself to be – that he will make straight – holes and all – our entire path. Before he said “light be” He had all my gaps, my crooked turns written down and already figured out how to “hedge” or “hug” me with His purpose for me. ( Ps 139).
    Keep doing what you guys are doing! You are revealing His glory in a new and special way.

      • Likewise to you guys and this site. Encouraging!
        I went all my adult life with very little to no contact with other men about their same sex attractions. Your openness, candor, honesty and hope. Is — Refreshing!!Strengthening!!! Lifesaving!!! Accepting!!!! All centered around the One who makes it all possible – Jesus. Thanks!!!!!

  • Cherish this- My first kiss wasn’t until my 20s. And it was from the wrong person. I had always said I wouldn’t kiss anyone till I knew for sure I was marrying them, male or female. I broke that rule and have definitely regretted it. So, don’t worry that you haven’t made the same mistakes as some of the other brothers on here- it doesn’t make you not fit in. It just means you have stayed strong in a way others of us haven’t. Thank you for sharing so openly, Tom.

  • I love your writing and your heart, Tom. My first kiss? I think I was 16 and parked outside a computer science class on the USC campus. I was so thunderstruck by the experience, we continued exploring our lips for the next two hours or so, looking for privacy in elevators and empty classrooms. Though you and I don’t have that in common, I know a bunch about regret and holes and consider you a brother.

  • I had been thinking about this today since the reading at church this morning included “Greet each other with a holy kiss.” Obviously that is a different kind of kiss, but it still got me thinking. One of the few concrete desires I ever had towards a male friend was wanting to kiss him on his cheek. On the lips seems less appealing.
    When I was maybe around 10, my female friends had some game that ended up with a quick peck on the lips. My guy friends at school actually thought it was pretty cool, tho I didn’t think much of it cuz it seemed more like kissing my family members. So I’m also 29 and still consider myself in the “never been kissed” category.
    I honestly don’t think about kissing much. I think I tend to feel more like I’m “missing out” when it comes to dating or especially sexual relationships.
    P.S. I want a cookies and cream milkshake now.

  • I too have never kissed and never even dated. But honestly I don’t think much over it, and I overcome social anxieties about it by simply saying “who cares?” The most longing and feelings of “missing out” is with intimate male friendships, not so much romance and dating.

    • Yeah, my “missing out” feelings also stem more from the realm of intimate friendship than romance. But it can be hard to ignore how everyone else around me has seemingly delved into the romantic realm.

      • Strangely I don’t envy romantic couples. Mainly because they seem to go on and on about how romantic love is the only kind of love worth having out there when I beg to differ of course. I think Phillio love can be just as beneficial, but sadly society at large doesn’t realize this.

      • It always starts out as “romantic” because we realize that need for connection has been unmet for some time. It’s like horses being pent up for the winter, and then released to the field, where they run and stretch, fart and neigh. But then it all dies down.

  • I’m 30 and never been kissed and I never used to think about this at all, but lately I have wondered what it is like to actually kiss someone and also what it means to be someone who has never kissed anyone. Does it change who am I? Do I seem naive to others about things? Is it yuck to mix bits of saliva?

  • Hey Tom, I am well over 40 and I have never been kissed or had sex either. It is likely that neither one will ever happen to me and I am very happy without those things! As long as I have a relationship with God and deep, meaningful friendships with other Christians, I am happy.
    Like you, I know this makes me different from most people, including other SSA guys, but I can always find common ground with other Christians who highly value God Himself. If someone has the most important thing in common with me there will be a bond despite whatever differences there are.

  • Well, I feel like the baby here on YOB being only 18 :). I have not been kissed. But, honestly, I don’t feel like I’m missing out on much. I feel like a kiss isn’t meaningful in and of itself. It’s the relationship between the two people that really makes it meaningful. I don’t view intimate friendships as off-limits (though kissing in that relationship, probably), so while my relationships with other people aren’t perfect, the human connection is definitely still there.

    • Honored to have you with us, Karl, 18-year-old baby though you are. You’re right, it’s more than the kiss I truly want. It’s the deep human connection more than anything, the hallowed kiss being just one of many expressions of said relationship. I’m ultimately yearning for healthy connections and friendships with men and women alike.

    • 1 Timothy 4:12… “Don’t let anyone look down on you because you are young, but set an example for the believers in speech, in conduct, in love, in faith and in purity.’

    • Hey Karl, The deep connection that you have with a man or woman if it’s intimate will lead to some form of kissing. In my experience with men, I was superficial. I was just using the person to get what I needed and leave. I never was in love. I did fall in love a few years back, but it was a different falling in love. Sure, kissing was involved, but it ended up being a friendship that has been wonderful and I never experienced having a beginning that was sexual, and then ended up not being sexual, but it grew into a platonic cuddling friendship where we do more talking and sharing. Our kisses now are dry pecks on the cheeks or lips. It’s the most different relationship that i have ever got myself into. LOL

  • Dude, I seriously love the hell out of you. Thank you so much for your example in resisting your flesh and this culture, and choosing to pursue God instead. Keep up the amazing work!!

    • LUKE. Finally you join us here. Welcome! Thanks so much for your support through the years. It’s good to know you and call you brother. Inspired by your walk as well.

  • I did not resist the flesh. I hope Luke still loves the hell out of me…well maybe not…I’m almost 59 now, but back in 1978 and 79 I got kissed a lot for about a year and a half. Man, you aren’t missing all that much. Kissing can be sloppy and wet with your buddy’s germs. I only did it because I loved him…I did. I have been celibate since, but I did it and much more. I feel like I do not regret my life then nearly enough, but I think He knows I repented of it and that I love Him now.
    I do admire your strength of character.

  • My first kiss was with a dude when I was 19. My first straight kiss was with my wife right after we said “I do”. That is something I don’t regret and never will. But I’m totally open to kissing my friends on the cheek or wherever (almost wherever) as a friendly expression of love. I mean, I kissed you that way. Does that count as a first kiss?

  • I am right there with you man, I also haven’t had a first kiss yet, or haven;t physically done anything intimate like that with anyone. It may sound cheesy and sappy (which is fine), but I really believe that one day I will get married, and so I don’t want to kiss anyone until my wedding day. My parents think that’s crazy but I just want to keep myself pure in that way for my wife only. Even when we are engaged I don’t think we will kiss.

  • I hated kissing. The very thought of all that saliva, and wet moistening and yuck ick , ewww. lol
    But about three years ago, I kissed a man for the first time. I was terrible. But the second time I had put more oomph into it and the guy I kissed said, “much better”. I thought, okay, I can kiss and I like kissing. After all these years, I started kissing at 48 LOLOL, and with a guy no less. Oh well. My kissing has been reduced to gesture kissing, or good night kisses. The reason why my kissing was reduced is because kissing is the entrance to an erection which leads to more stuff. I didn’t like that and moved away from it. At least for now. I have no idea what God has planned for me down the road.

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