Chapter 5: Learning Social Skills and How to Deal with Shyness

By the time I went on my first real date as a college senior, it felt less like a rite of passage and more like a miracle. I had spent years watching others fall in love, flirt, and fumble their way into relationships, while I stood on the outside, silent and unsure of how to even begin.

I hadn’t dated in high school. I hadn’t dated in the first four years of college. It wasn’t that I didn’t want to—God, I did. It was that I didn’t know how. Wanting something doesn’t mean you believe it’s possible. For me, connection was something I studied, not something I expected.

Everything changed when I began working with my counselor. In our sessions, we dissected the simplest interactions like they were foreign languages—how to ask a question, how to read someone’s interest, how to keep a conversation alive beyond one-word replies. He gave me articles, handouts, real tools. I took them seriously. I had to.

We talked about “free information”—weather, classwork, clothes. Casual, harmless entry points into a conversation. Then came the art of active listening. Reflect, rephrase, ask open-ended questions. I practiced these techniques like my life depended on it—because in a way, it did. My social life, my sense of worth, my hope for love and connection—they were all tied to learning these skills.

My counselor also ran a therapy group. That group became a lab for human connection. We role-played awkward scenarios, rehearsed how to speak up, how to assert ourselves. I was surprised by how many people there felt the same way I did—awkward, unsure, invisible. It gave me a strange kind of hope: maybe I wasn’t broken. Maybe I was just inexperienced.

I was learning social and communication skills. 

But therapy didn’t stop when I left the office or group room. I carried it with me—literally.

In my backpack, I always kept a pad of paper and a pen. I was doing something my counselor called the Three-Column Technique, a classic Cognitive Behavioral Therapy tool. At first, it felt clinical—structured and awkward. But over time, it became my anchor.

Column One: the thought. The fear.

“She won’t want to talk to me.”
“I’m going to embarrass myself.”
“I’m too weird. Too quiet. Too boring.”

Column Two: the distortion.
Predicting the future. Mind-reading. All-or-nothing thinking.

Column Three: the challenge.
What’s the evidence this thought is true?
Have people actually said I’m boring?

Aren’t there times I’ve made someone laugh or smiled at just the right moment?

I filled page after page with these thoughts. In classrooms, at the frat parties, walking across campus—I was battling my brain. And it was a battle. Each interaction required strategy and courage. I didn’t want to fake confidence. I wanted to earn it.

I was learning that shyness wasn’t just a personality trait—it was a shield. To me, it seemed like “shyness” was weak term because I thought there was something about myself that could be diagnosed. A certain sickness that would explain why I was so “different.” It was a survival strategy. One I had outgrown, but didn’t know how to lay down. Every time I avoided a conversation, I felt a fleeting relief—like dodging a bullet. But afterward came the self-loathing. The shame. The deeper invisibility.

This technique gave me a way to interrupt the cycle. It didn’t erase the fear, but it gave me something stronger: a sense of agency. For the first time in my life, I could do something about my anxiety besides disappear.

Always being the Extra Person

Despite all the skills I was practicing—therapy groups, CBT worksheets, active listening techniques—I still couldn’t cross a certain threshold. I never met a girl directly at a party or in the cafeteria. The women I got to know were friends of friends, or already paired with people I trusted deeply.

I was always the extra person. The third wheel. The safe guy.

Thomas, my best friend, trusted me completely around his girlfriend, Jo-Lee. That trust wasn’t misplaced. I never crossed boundaries—but I couldn’t help noticing how easily the two of them clicked. There was something graceful in how they touched each other’s arms, how they laughed without hesitance. It didn’t make me jealous exactly—it just reminded me of what I still didn’t have.

After Thomas graduated and moved north, I grew even closer to Jo-Lee. We spent time together like real friends—eating lunch, talking about life. I never made a move, never thought to. That wasn’t what our connection was about. But her presence reminded me that I could connect. That I wasn’t completely invisible.

Another friend of mine had a girlfriend too. We all hung out, and I got close to her as well. We even went to Florida together with my sister over a school break. I was trusted. I was safe. I was kind.

But I still wasn’t chosen.

Dancing with the Maid of Honor

Thomas and Jo-Lee eventually got married. Their wedding was beautiful—warm, local, filled with faces I mostly didn’t know.

I was the best man. That role came with expectations, including a dance—a horrifying ritual for someone still uncomfortable in his own skin. I’d never danced. Not really. Not even at prom - I had never gone to a prom.

That’s when Jo-Lee asked her maid of honor, Mary, to show me how.

Mary was stunning. The kind of stunning that makes you forget what you’re supposed to be doing. Her dress was low-cut and emphasized her full chest, and I hate admitting how much that distracted me. I was trying to focus on what I was going to be required to do.

What about Thomas? I thought about that. I wasn’t entirely alone in my insecurities. How did things even take off with Thomas becoming engaged to and not getting married to Jo-Lee? If guys had to make the first move and ask out the girl then how the hell did Thomas arrive at this point? Thomas was like me. I don’t even remember anyone pulling him out to dance at a fraternity party. That had happened to me. It had happened to me. I think it happened with one of the girls that some of my frat brothers tried to hook me up with. Someone who they hoped would have given me an experience that night that I never had. Instead I had disappeared into the crowd of people and into myself.

Anyway, here we were. I didn’t know who was giving Thomas lessons in what for us would have been the infamous experience of dancing - it’s tragic that for some of us this is so unnatural, embarrassing and something to be avoided. Thomas was into great rock songs and I assumed there was an inverse relationship between music made for dance and good music.

Music could create the atmosphere for a horror movie and that never inspired one to get up and dance. Decades later, I noticed with shock that even Pink Floyd employed dancers. I thought they would have been called backup singers. My interest in music was specifically limited to music that I assumed people couldn’t dance to. This has been strange and tragic.

For lack of a better term, I was phobic of dancing. As such, one tries to figure out the potential origin of this single event learning. Was it from my mother describing in a moment of unusual and unexpected joy as a child just being able to walk, I did something that took on a certain life and I chose to “do a little dance?” That is the shameful quote that echoed across the decades toward eternity. Who knows but moving as if one were “dancing” has always too embarrassing.

It was something far beyond being a bad dancer. Dancing is both normative and common as well as something worthy of recognition for one’s skills. My insecurity extended far beyond being insecure.

Jo-Lee had stepped in. She explained the situation of me not having even the most rudimentary skills in dancing and knowing that I was very anxious about this part of being the best man.

Yet, like Thomas we had to participate in a formarlity. My instructor or tutor was the maid of honor, Mary.

She was kind about it. Patient. She guided me through the rhythm gently, probably sensing my discomfort. And for a moment, I wondered if I should ask her out.

I felt sorry for Thomas who also had to engage in this ritual of a similar "dance" that he would hate as much as I did, I imagine.

Noticing Marleesa

I had not actually discussed with Jo-Lee that I was attracted to Mary the maid of honor. Perhaps I assumed that someone with feminine features that were generically attractive to guys would have meant she had better choices than me.

At a party after the wedding, it was obvious to some that Marleesa was interested in me. I couldn’t believe that. It was just not something I had experienced. My strength and muscle tone were not recognizeable as far as I could tell. There had been something called a “Greek God” event in which fraternities could choose someone to particpate if they could lift their entire weight over their head.

I had shocked people as I was struggling with my identity as a guy. I didn’t embrace all the things that reflected being a guy. However, unlike what you see on TV shows like Law & Order: SVU, I had never known anyone who hurt a girl and made it seem acceptable. I have previously pointed out that I was recognizing the feminine side of myself. Yet, indeed, I was much stronger than most if not all of my frat brothers, pound for pound. When I went with frat brothers to the place on campus for us to work out, the newest people to join the crowd thought they were lowering the weights for my sets.

In reality, someone would explain, “no we are going up in weight for Bruce.”

I had run a half-marathon and probably didn’t have anything other than muscle on me, yet, I still couldn’t begin to imagine myself as attractive to anyone.

So when Marleesa was into me, I hadn’t noticed. Or maybe I refused to notice because this was entirely new to me. A part of me couldn’t believe it. If in fact girls waited for a guy to make the first move that would explain why I had not had any experience dating.

Jo-Lee must have seen the disbelief on my face because she doubled down. “Seriously, Bruce. She’s been trying to get your attention all night.”

I looked over at Marleesa. She was pretty, too. Sweet-looking. Warm. I hadn’t really taken her in before. I think I had trained myself for years, for my entire life not to notice or think about someone being into me. Better to assume no one was interested. Easier than hoping.

But once I looked—really looked—I saw it. The way she kept glancing in my direction. The way she subtly positioned herself nearby.

There was even this moment with a dog. The family dog kept bothering me at one of this post-wedding gathering. I didn’t say anything, but I was visibly annoyed. Marleesa noticed. She got the dog away from me, gently, protectively. Then she glanced back, checking to see if I was okay.

That one moment, more than anything, made it real. I looked over at Thomas and Jo-Lee. They both raised their eyebrows at me, like See?

It might have been a small gesture but even I noticed it. “I think she likes me.” I said to both of them.

“You think,” asked Thomas in way that was almost filled with laughter.

Jo-Lee was like “Go say soemthing to her.” 
 

I said, “yeah, I’m not a dog person and it was nice of her.” They knew I was a cat person.

Jo-Lee was like “nice?! That’s all you can say? What have you been waiting for?”

She wasn’t just talking about the situation with Marleesa. I had not dated at all. I probably hadn’t told her about the girl at the post office where I worked.

The First Real Invitation

Eventually, Marleesa invited me to something—an Easter play her church was putting on. She had a role in it, and she seemed genuinely excited for me to be there.

This wasn’t subtle. This wasn’t “maybe she’s into me.” This was a real invitation.

I said yes.

I assumed now for the first time in my life that someone had chosen me.”

After the performance, we walked together outside under the night sky. The air was comfortable. The stars were out. I was thinking about how much she was into me - which was hard for me to process. I was very religiously conservative at the time. But a kiss at this point and with someone so into me seemed like what she would expect. And clearly she was not shy like me. That was clear from my interactions with Jo-lee. I was shy like Thomas. I was the one who needed help.

I leaned in, slowly, gently, hesitantly.

And she turned her head away. This was at once bizarre and embarrassing. No, I had not done anything remotely forceful. This was minimal in terms of what some of my frat brothers wanted to happen for me with a girl.

Shame and Silence

It wasn’t rejection in the cruel sense. There was no harshness. No disgust. But it was clear—this wasn’t the moment I thought it was. No I just didn’t understand and I was ashamed. Despite not acting in any way forceful, I felt like I had done something bad.

When it happened, I froze. Didn’t say a word. Just stood there, humiliated. My face went hot. My thoughts collapsed inward.

I read it wrong.

How could I be so stupid?

I didn’t know how these things worked. I couldn’t convince myself that I had not done anything wrong. I had not acted like she owed it to me.

It wasn’t just the kiss. It was everything I’d been working toward—every CBT column I’d filled, every group session I’d sweated through, every hopeful thought I’d barely let myself believe.

And now it all felt undone.

I didn’t lash out. I didn’t push. I didn’t even ask for an explanation. I just… disappeared. Slipped back into the silence I knew so well.

That was the last time I saw her. Just like with Michelle, the girl that I worked with at the post office. I let embarrassment get the best of me. To be honest, I had not actually been very invested in the relationship with Marleesa. I was just moved by the idea that someone was that interested in me.

I would have liked to and could have gotten a kiss from Michelle, the girl from the post office even though I had broken a dating rule… If I had just said the things I thought about after the fact. Telling her how special she was and how much time I spent trying to get the courage to ask her out.

With Marleesa, I just didn’t cross her path again. She was going to another college. I just avoided talking about what I felt when I saw the girl at the post office.