With Valentine’s Day right around the corner, I’ve been thinking a lot lately about the nature of romantic relationships—the joy they provoke, the agony that can ensue, and the everlasting marks they tend to leave on our hearts.
Before I met my husband at the tender age of 21, there was a small handful of boys (men?) that made a brief appearance in my mostly uneventful love life. And although I only officially dated one, I can honestly say that I learned a thing or two from all of them. Which is what sparked an idea: Rather than bore you with tales of my happily ever after (February doesn’t need any more mush), why not give tribute to the failed romantic endeavors that shaped my past? After all, these are the stories that we never forget.
So here’s how this is going to work: Three guys, three separate posts. At the risk of getting way too personal, I’ll tell you what happened and what I took away from it—in hopes that at the very least, my dating disasters will invoke a bit of laughter on your end, or perhaps some sisterly solidarity. Because we’ve all been there: stranded helpless on this cold battlefield we call love.
Without further ado, I give you Part I of my three-part series starring the (slightly stereotypical) Mr. Wrongs that, looking back, might have led to something right! Let’s begin with…
The Emotionally Wounded Serial Cheater
THE STORY // I have to give myself a pass for this first one, because I was a wee thing at the time: only 15 years young, completely naïve, and head-over-heels “in love” with the hunk of my high school theatre department. I met him on the first day of my freshman year, and it was infatuation at first sight. He—let’s call him Cliff for the sake of this post, shall we?—was two years my senior, couldn’t so much as look at a girl without flirting, and had a head full of voluminous hair that would’ve made Justin Bieber jealous. Never in a million years did I think someone like Cliff would give little ol’ me a second glance, as timid and unexperienced as I was, but the stars just happened to align one September day:
We were chosen opposite one another as lovers in a school play.
After that, Cliff and I became fast friends and it wasn’t long before he began entrusting me with his deepest, darkest secrets via AIM (remember that?). Within only a couple months of knowing him, I had learned about the anger he harbored from his parents’ divorce, his nighttime ritual of writing poetry to cope (swoon!), and the real reason his ex-girlfriend had dumped him: he had a bad habit of putting his lips where they didn’t belong.
But did I care? Not one bit. I was trying to find my place in this scary world called high school, and Cliff was the first guy that ever made me feel important. In the poetic words of Mia Thermopolis, he saw me when I was invisible. (Sorry, had to.)
So when he finally asked me to be his girlfriend on a particularly sunny day that following June, I didn’t think twice—despite my mother’s wishes. (Fifteen-year-olds, amIright?) Needless to say, we had a wonderful (albeit brief) summer together, the most memorable evenings spent riding around town in his best friend’s car and singing along to the Moulin Rouge soundtrack at the top of our lungs. Life was down right dreamy for a hot second, and I was over the moon.
Then the inevitable happened: Cliff hooked up with the same ex-girlfriend he had cheated on before me. Classic.
THE TAKEAWAY // I know, I know. Should have seen that one coming, right? (Mom, you can wipe that smug look off your face. Love you!) As pathetic as this particular experience was, it taught me a very valuable lesson in dating, which is: If a guy was unfaithful to a previous partner, he probably won’t be faithful to you. But more importantly, I learned that opening yourself up to vulnerability won’t kill you. Being dumped is not the end of the world, and being bitter about being dumped won’t mend your broken heart.
Even then, I knew that Cliff wasn’t a bad guy. He was just as young and confused as I was, and we were both learning to navigate the hormonal mess that is public high school. The night our summer romance ended, I cried for five minutes alone in my room and then called my closest girlfriend, who helped me laugh the whole thing off. At rehearsal the next week, I looked Cliff square in the eye and smiled. Because it was then that I understood that I had survived my first love—and my first heartbreak—without so much as a scratch to show for it. Turns out, this timid little thing was much stronger than she thought.
Photos from The Princess Diaries by Walt Disney Company.
Co-Founder & Editor | Emily graduated from the University of Texas in December 2013 with a degree in English and journalism under her belt. She currently lives with her husband in Frisco, where she works for a chiropractor and moonlights as a lifestyle blogger. On any given day, you can find her hanging out at a quiet coffee shop, nose-deep in a good mystery novel or snapping photos of her extra frothy cappuccino.