Recently, during a small gathering of friends, the question was asked, “what is the most embarrassing moment of your life?”  Many of these stories were being shared publicly for the first time.  As I listened, I felt honored to hear my friend’s heartfelt answers ranging from; public speaking mishaps, issues with bodily fluids, and serious wardrobe malfunctions.

What was clear about all of these embarrassing moments is the individual internalized and/or held onto the memory for a significant period of time.  I can’t speak for my friends, but I’m guessing that to be classified as one’s “most embarrassing moment” there has to be an element of shame involved as well.  In my case, both held true.

The horrible, shameful, no-good moment that caused me years of torment (not an overstatement), occurred during my Sophomore year in high school.  This is the painful (for me) story of how I messed up a kiss.

As a teenager who was overly preoccupied with sports, I didn’t make a lot of space in my life for girls.  Or, that’s what I told myself anyway.  The truth is, in high school, I didn’t have a lot of experience interacting with the opposite sex and I was pretty damn intimidated of any “lady” who happened to wear Sunflowers perfume, clothing from Express, and/or listened to 90’s grunge music.  Basically, I was scared of the entire female population between the ages of 14 – 20.

With my fear of women properly established, imagine my excitement, horror, and trepidation as I walked down the high school halls with my “girlfriend” of two weeks.  To protect the confidentiality of this now married, 40-something-year-old woman, with 5 beautiful children, let’s call her Debbie (definitely not her real name).  As Debbie and I walked down the halls, I’m guessing the conversation was incredibly deep and intellectually profound as we both shared our thoughts on Reductionism Philosophy, our favorite Buddhist Suttras, and our views on String Theory.  Said another way, we were both talking about what we were going to do that weekend.

As the conversation started to wind down, the hallway became ominously empty.  Just then, the bell rang announcing the beginning of the next period of classes.  Looking up at Debbie, we made eye-contact for the first time during the entire walk. 

She was looking at me.

I was looking at her.

There was no one in the hall.

The thought, “you are supposed to give her a goodbye kiss,” crossed my mind.

The next thought of “DON’T F*CK THIS UP!” followed soon after.

We were still looking at each other.

I was praying that someone would save me.

No one saved me.

I went in for the kiss, staring at the cherry lip gloss on her lips.

I closed my eyes, smelling the Herbal Essences shampoo in her hair.

I moved my face further.

And I…

kissed her on the shoulder.

Maybe it was her neck!  Maybe it was her cheek?  It actually could have been her lips!?  But wherever my kiss landed, it didn’t feel like that magical WB Channel goodbye kiss you see on Dawson’s Creek.  Petrified that I had in fact, “f*cked it up”, I did what any smooth Dawson wannabe would do after kissing his Joey…I ran.

I ran as fast as I could down the deserted hallways of my high school, with my heartbeat racing, my Timberlands bouncing, and my middle-parted hair flopping.  Sweating, shaking, and panic’d, I soon made it to the safety and comfort of Alegbra 2, a class I hated, and would cheat my way to a “C” grade.  No matter the subject, I was just so grateful to be far away from that female monster with her Medusa like curly blonde hair, piercing blue eyes, and demonic freckles!

Just then a supportive friend probably by the name of Jordie or Jimmy said, “are you ok Dan?” 

Not one to kiss and tell, I responded with, “no, I just f*cked up kissing Debbie.”

With great care, my friend replied, “how the hell do you f*ck up a kiss?”

I tentatively said, “I think I kissed her on the shoulder.”

Conscious of my feelings and knowing this was a sensitive time in my life, my friend replied with, “HAHAHAHHAHAHAHAHA, YOU DUMBASS!”  Like I said, a supportive friend.

At this point, my mind went back to Debbie.  Although the thought of being close to her again scared me to no end, I still “liked” her and wanted her to “like” me.  Knowing that I didn’t have the guts to see her before school let out, I decided I would call her that night and see if she wanted to do something over the weekend (when I would have more guts).

After school, I pulled the basement telephone into the privacy of our family guest bedroom.  Staring at the phone, I practiced what I would say for at least an hour.  Finally, drawing on the power of Grayskull, I dialed the 7 digits and held my breath waiting for Debbie to pick up.  On the 3rd ring, I did the sensible thing and hung up before anyone could answer.

“Whew, that was close.”

30 minutes later (and after a couple games of NHL95 to cool down), it was time to try again…

Picking up the phone, I dialed and prayed to Yoda and The Force that this time would go better than before.  Instead, Debbie’s Dad answered…

“Oh hi Mr. Archinz (probably not their real name), is Debbie there?  This is Dan.” 

Mr. Archinz, “No, sorry Dan, can I take a message for her?”

Me, “Uhhhh, can you tell her to please call me back?”

Mr. Archinz, “sure thing Dan.”

I hung up the phone and waited.

And waited.

And waited.

She didn’t call back on Friday.  She didn’t call back on Saturday.  I was beginning to get an idea as to what was coming.

Sunday evening, I got the phone call and heard the fateful words…

“Dan, I think we should just be friends.”

It’s been 27 years since that day, so my recollection of events could be completely off, but what I remember is feeling a sense of relief.  Relief that I didn’t have to worry anymore about what I was going to say to sound cool (aka “be good enough”).  Relief that I didn’t have to worry about messing up any more goodbye kisses.  Relief that I could go back to just being me again.

But who am I kidding?  After the relief washed over me, I was sad, embarrassed, and hurt.

Unfortunately for me, I hadn’t yet acquired the tools and confidence to quickly get over an embarrassing moment such as this.  Rather than dust myself off, chalk up the awkward kiss to inexperience, and love myself (not the kind of self-love that occurs by yourself behind closed doors), I beat myself up mentally and further developed the story that I just wasn’t “good with girls.”  Low and behold, the story I developed stuck (why wouldn’t it? – I believed it!) and throughout high school, college, and into my early 20’s, I can’t say I had a ton of enjoyable dating relationships.

Let’s be clear, Debbie had very little to do with the story I had created in my mind. This was 100% of my own doing. While I had gotten myself into this mess, re-writing the narrative would take help.  What ultimately worked was a little bit of therapy (showing me the importance of finding appropriate tools to deal with my thoughts), gaining additional confidence (maturity), and meeting a wonderful woman who loved me for me, no matter how awkward I was.  That woman is now my wife and time has shown me that she’s clearly my equal in the goofy department!

Back to the embarrassing “shoulder kiss” for a moment.  What is it about certain episodes in our life that have a disproportionate impact on us?  My best guess is this moment was MOST embarrassing for me due to the following:

• I had a very fragile ego – I saw failure as death, rather than a learning opportunity
• I cared more about what the other person thought of me, than what I thought of myself
• I learned from society (Hollywood?) that messing up a kiss was a TERRIBLE thing to do
• I felt alone.  The experience felt exclusive to me, as though I was the only person on earth who has failed to hit the target with a kiss.
• I created a faulty narrative that followed me into the future

While all of the above helped to contribute to this embarrassing moment, I believe the faulty narrative of, “I am bad with girls,” was the most damaging. What to do with the (usually wrong) stories we tell ourselves!? If I had known about The Thinking Path when I was 15, it could have done me a world of good.

The Thinking Path is essentially Cognitive Behavioral Therapy and helps to restructure the way the mind thinks and perceives situations. I’ve written about this framework in the past, but it’s worth repeating:

• our THOUGHTS create our FEELINGS
• our FEELINGS create our ACTIONS
• our ACTIONS provide our RESULTS

In my case, the thoughts of “being bad with girls” led to feelings such as fear and sadness. Being fearful led me to act in a nervous manner and/or say/do things that weren’t my authentic self. These inauthentic actions led to less than amazing relationships with women. For years, I dwelled on my lackluster relationships (results). It wasn’t until I started focusing on the thoughts that were swirling around my mind when my feelings, actions, and results improved.

Whatever your “most embarrassing moment” may be, I hope you have found the space to be kind to yourself and realize that the story you may be telling yourself ain’t the truth. It took longer than I would have liked, but I eventually realized everyone makes mistakes and even Dawson messes up a kiss every once in awhile…right?

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Author Bio: Dan started Fired and Free in 2017, to provide his “truth” after being fired as CEO of the company he started and led. After a diverse 17-year career in management consulting and entrepreneurship, Dan now leads 3Sixty Leadership, where he provides coaching and consulting to business owners, helping them to improve their leadership and company culture.