The Confidence Conundrum


It’s like this captcha can stare into my soul.

I was recently in line at a store, about to check out, when a beautiful woman walked by me, her eyes locked onto mine. As if we were suddenly yanked into a teen sex comedy, time slowed down as she entered my line of vision: her red lips had the slightest, knowing upturn of a smile; her orange curls framing her caramel skin bouncing and swaying; her walk as confident as the decision to wear painted-on jeans.

The exchange was probably five seconds at the most, but it felt like an eternity. Somewhere between year 2 of her tractor beam gaze, I had to internally yell at myself, “SMILE, DAMMIT!” And I THINK I did. But it felt forced, not natural. It generated anxiety, not ease. And the whole time, I wondered when it would all be revealed to be a joke at my expense.

These are my experiences when it comes to interactions with attractive women. More than that, it signifies how I encounter my life.


The last time I was home, my mom asked me an interesting question. “What could I have done to help you with your confidence?” she inquired, kind eyes searching mine for an answer to a problem plaguing me for more than 20 years. I had to collect my thoughts, as I like and need to take time to formulate and articulate things for maximum efficiency. (I’m not much of a talker.) Simply saying “yes” or “no” would have been too simple; an explanation was necessary. But which one of dozens could have sufficed?

  • Freshman year of high school, when two seniors befriended me in a year-long prank–including one of them stabbing my hand with an X-Acto knife in art class?
  • My dad and a family friend mocking me for outing my early internet porn browsing?
  • A former high school friend, after my obsessive efforts to rekindle our friendship, sending his goons to my door to emotionally frighten me? (Mission accomplished!)
  • Freshman year of college, being driven off my dorm floor by my former roommate and his friends after I had the audacity to get another room due to his loud late nights?

So I said “no,” letting her know that she alone couldn’t have been responsible for or carrying the burden of my fragile self-esteem. I then recounted an example that I thought at the time would give insight into the genesis of the issue. Upon further glance, it revealed more than I originally intended.


It was the summer of 1993. I was enjoying time off after a terrible seventh grade year, my full indoctrination into the Lord of the Flies-like world of teenage society. I was a chubby 13 year old with a Kid ‘N Play haircut, so I was naturally a target for bullying and other derision. My fashion sense for sweatpants and hiking boots didn’t help matters. Having pencil shavings dumped in my hair and a sign put on my back was the worst of the abuse, and being verbally mocked was a common occurrence.

I got word from my friends that the homeroom postings for the pending school year were posted at the junior high. As I couldn’t legally drive at the time (and my parents both drove manual-transmission cars, further ruining any joyriding fantasies), I waited for my dad to get home so I could get my school marching papers. My relationship with my father at the time was degrading; aside from the general teen embarrassment of being seen with their parents, I found myself on the receiving end of his frustration with life via occasional comments and put-downs (with some yelling),  making me feel even worse about myself. (My younger brother wasn’t too shabby at teasing me like it was his full-time job.)

So we pulled up to the school, and I noticed several girls that were instrumental in the collegial torment. I didn’t want to exit the somewhat safer confines of the car, but I knew that my dad would get upset (another typical transaction for thinking independently back then), so I grudgingly slinked out. And as I approached the front doors of the school, the girls locked onto me, launching into verbal attacks not different from what transpired months before. (They were at least consistent.) I soldiered on, got my information posted on the doors, turned around and walked back to the car as their strikes hit my back.

When I got back in the car, I immediately launched a ramp-up to Sobtown. My dad, ever the compassionate person, yelled at me to not cry, to show them that they didn’t hurt me. Now fighting shame on two ends, I choked back my tears until I got home, where my mom consoled me in the bathroom.


In hindsight, that event marked the end of several things in my life: my blind trust in my father as an emotional base; my ability to fully expression my emotions; and any hope of escaping social situations unscathed. My relationship with my dad would deteriorate further–including him lying to my face about his affair–and still troubles me to this day for the fact that I can never fully connect with the selfish man that I once looked up to.

My mom listened to my story (which was shorter than what I wrote above), and she remarked that my dad’s rally cry to be a man and not be upset was something he learned from my grandfather (his father, natch). She wondered aloud if she should have left my father earlier, which probably wouldn’t have helped things. The seeds had been sewn years before those events, and future encounters preyed upon my weaknesses.

As my conversation with my mother took place on Father’s Day weekend, one where I met with my dad for about an hour in a comically strange get-together that will be fodder for my next therapist, I thought about my desire to be a father. My mom remarked earlier in my visit that my brother, my cousin and I wanted to be dads despite the emotional and physical absenteeism we faced with our biological fathers, and that our devotion and compassion would make for better examples for current and future children. I hope I can overcome my own issues to make this happen.


The woman that I encountered the other day reminded me of two similar happenings back in college, both involving attractive women saying hi to me, and both ending with a dumbstruck me not being able to respond. I was a sexual late bloomer, not even having a kiss with a girl at that point. Though I summoned up the courage to eventually have a few dates by the time I graduated, my kiss-less streak continued. I was too shy and naive to follow up on clear flirtations from several women, I chased after the wrong girls (as in emotionally unavailable and not attracted to me in the same way), and I had no clue about what I was doing or seeking.

I recognized back in college that I needed help for my trust issues and emotional insecurities, and I sought counseling from on- and off-campus resources. Unlike my commitment to my video games and getting out of college with a degree, my committal to my mental health wasn’t strong, abandoning the sessions after a few tries. (Also, specialists are costly for a college student–even with help from a parent.) I would pick up and put down my efforts to better emotional well-being throughout my adult life with some gains, and I’m currently contemplating a return for a much-needed tune-up. I wouldn’t be surprised if my inability to fully invest in a counselor for an extended period of time is connected to trust issues. (IRONY!)

Those same trust issues have plagued my relationships during my grown-ass man stage. Not being emotionally secure has manifested in doubt in the sincerity of bonds with most of my friends, wondering why they would want to be connected to me. It has popped up in insecurity with the one romantic relationship I’ve had, a long-distance accord that ended (after increasingly bizarre comments and misgivings from her) with her calling it off and connecting immediately with the man she would marry. And I’m still conflicted when it comes to my close relationships–be it with family and best friends. In summary, my shyness, disbelief and mistrust are consistently duking it out.


I’m not sure why I wrote this blog entry. I initially wanted to recount a personal story about myself, but it morphed into a more painful deep-dive (a marketing term I hate) into my emotional bedrock. I clearly want to share a bit of myself–not unlike your annoying Facebook friend that posts a daily selfie in a visual cry for help. But maybe, JUST MAYBE, someone will get something out of this–whether it’s understanding why I write what I do, or that it’s okay to seek help for self-esteem. Maybe I want to give my mom a better answer to her question of how she could have helped me emotionally. Or maybe, JUST MAYBE, I want to believe that I can look back at this piece of writing as something along my road to recovery. I guess that would mean that I have a bit of confidence in something that is desperately needed: confidence in myself.



9 thoughts on “The Confidence Conundrum

    1. I’m glad to hear that your husband is a great father and could relate to experience. Thanks for sharing that, and I’m glad that you shared the blog entry. I admire your writing, so it’s high praise that you’re reading mine. ^_^


  1. Hi Trevor? I once heard joel osteen preach and he said `don’t let your past experiences cause you to become mediocre.’ I’ve held on to that quote cuz i believe it applies to everyone. I mean everyone has a past that isn’t exactly rosy. You sound like a wonderful man just from the way you articulate yourself in your posts. Work on building yourself and if you are a Christian and believe in prayer, constantly ask God to give you confidence in yourself. I will come back again to comment on a post you have posted after your wedding to that amazing woman. Cheers!


  2. Hey Trevor. Thank you for sharing your experience. I wanted to tell you again how sorry I was for teasing you. I was wrong and I hope you can forgive me. It took a lot of courage to write this. You are my best friend and I’m very proud of you.


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