Every time I think about my High School Sunday Boyfriend, I can’t help but picture scenarios as if we are in an ‘80s Molly Ringwald movie. Maybe it’s because that is the time we were in high school together? Maybe it’s my red hair? Maybe a combination? Your guess is as good as mine. But […]

Every time I think about my High School Sunday Boyfriend, I can’t help but picture scenarios as if we are in an ‘80s Molly Ringwald movie. Maybe it’s because that is the time we were in high school together? Maybe it’s my red hair? Maybe a combination? Your guess is as good as mine. But the scenario is always the same in my head…Molly, er rather; Katie gets the cute boy (my HS SB) in the end.

In real life this didn’t happen. My High School SB and I never dated, let alone played out any perfect 16 year-old birthday kiss from Jake Ryan. Mostly because when I was 16, I was shy and still trying to figure out how to let my voice out. Back then I felt like Janis Joplin stuck in a Holly Hobby world: a girl with strong opinions, but unsure how to utilize them to get to be the woman I wanted to be. I was deathly insecure of letting out my opinions for fear of being disliked. I struggled, like most teenagers do, to find a place to fit in. I was trapped in the muck of defining what a “good girl” really is. My inner Janis said one thing, my outward Holly did another. And my feelings for my HS SB were stuck in the middle. I wish I would have learned that being a good girl wasn’t as black and white of a definition as I thought it was. In reality, good girls, happier girls, are many shades of grey.

My High School Sunday Boyfriend was the guy that stirred my hormone pot. We can all identify someone who used to make us all a flutter when the mere mention of their name popped up, right? Heck, I still get flushed when I think about a pre-puffy James Spader. [Why Molly’s character in Pretty In Pink, Andie, went for whiny Blane (McCartney) over cocky Steff (Spader) I’ll never know.] My HS SB’s dark eyes, dark hair, oozing confidence, killer smile, and flirtatious bad-boy persona were just the right combination to stir my inner Janis’ salacious thoughts. Suddenly my “good girl” definition took a dramatic turn towards grey.

But I remained shy and insecure, so I didn’t do anything to set my inner Janis free. I continued to try to stifle her by telling myself he was, “Out of my league so why bother. Just stay friendly so you can still talk to him. It’s better than nothing.” This…and I can’t stress this enough…put-down way of thinking will do nothing but keep you away from the things you want. And I’m not just talking about the guy you want. I’m talking about the degree you want; the job you want; the dreams you want. I wish high schools, heck even grade schools, would offer classes on teaching young people, especially girls, to overcome their fear of being themselves. Because fear does nothing but make a bedfellow out of regret.

Hey, no worries. I eventually learned how to marry my inner Janis with a new, grey definition of “good girl,” which is: going after what you want is good and girls should do it more often.

My HS SB was, and continues to be, the kind of person that can put anyone at ease. He has the uncanny ability to turn cocky, flirty behavior into intoxication. He is incredibly comfortable with himself. He has no qualms throwing in a one liner during the heaviest of debates. And this is a tad cocky…but I like the way it can throw you off and keep you on your toes. Plus, it’s hard to look away from him when he talks (and not just because he’s cute). No matter the subject, he looks right at you when he both talks and listens. Not everyone does this…looks at you when you talk. Try doing it during your next conversation and you’ll see what I mean. But to my HS SB, it’s second nature. And who doesn’t like it when they are heard? Yeah, the answer is nobody. That’s one reason, I believe, he was so popular in high school and continues to be well-liked. 

The high school we went to was small. With less than 100 kids in our graduating class, everyone “knew” everyone. There were still clicks, but by our senior year, we managed to find a way to interact with everyone enough to know when something was out of sync with anyone. So when my HS SB started to withdraw from people and events, there was a small group of us that knew something was up. We would talk about it from time to time but, because of my shyness, I never directly asked him what was wrong at the time. But it was clear something was wrong. His outward personality suddenly became withdrawn. He was usually by himself, by choice, at lunch. He didn’t smile as much anymore. It wasn’t until years later, after telling my HS SB of my secret crush, that I found out what he was dealing with. Upon finding out, I again wished I had let my Janis out earlier in my life. Silence is another of regrets’ mistresses.

I can’t say that I would have been much help to him had I known at the time. Because even though the heart was, and continues to be, willing to help in any way, I’m not sure I had the maturity to offer much more than a friendly ear to listen. No question I had that to offer. But, honestly, what could I tell him that would ease his confusion and frustration of suddenly feeling anxious in crowds?

After high school my High School SB and I drifted apart. We would occasionally run into one another the first five years after high school. But as what usually happens in life, the struggle to become the men and women we have always wanted to be takes control of our time. Friendships, if not continually nurtured, take a backseat. So fast forward to technology’s darling, Facebook, and our milestone HS reunion and voila…a reconnection is made.

I seized the opportunity to communicate after years of regret of not only telling him how I felt back in the day, but also finding out what was wrong. First for the crush. The words that came out of my mouth, to my surprise, were, “I basically would have cut off my right arm just to have a date with you.” He chuckled, looked me right in the eye when he said he was flattered and wished he would have known. Sigh. Flattering him was really all I wanted to accomplish by sharing it, but it turned out I was able to put a nagging question of “what if” to bed. And even though there was nothing either one of us could do to reverse time, we were able to renew a friendship based on open kindness. And what enhanced this renewal was sharing some of our life experiences that brought us to the place we are today. My admiration for my HS SB grew after hearing how he survived some of life’s darkest sides and found love with his wife and two beautiful children. When men open up and share their love for their families, it is a moment of true tenderness. I was honored to hear not only that, but also discover the story of how he dropped out of college to figure a way out of that darkness and is now back in school to become a teacher to children with special needs.  His ability to put things in perspective and keep moving forward motivates me to keep moving forward, too.

Here’s hoping all of you, when given the choice, put your fear aside, move forward, and seize the opportunity to discover how great it is being a good girl in the grey.
As always, remember to be good to yourself, your Sunday Boyfriends, and stay comfy.

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