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First Heartbreak 

 March 18, 2022

By  Jessica Biles

Heartbreak is inevitable. My first was around the 8th grade or so. He was never even my boyfriend. Yet I cried about him like he had been the love of my young life. I don’t want to forget this painful experience because it’s memories like these that keep me open minded to my own daughter’s journey through life.

His name was *Chad, which may or may not have been short for *Chadwick. He was a quiet boy, a good boy, a Christian boy. He was cute, not incredibly tall but taller than me. Tick, tick, tick, he checked off all my boxes of what I thought I wanted in 8th grade. Ironically, I married a man with these same qualities which shows that even though I deviated from my list as I dated in later years, the type of man I wanted to marry never really changed.

The difference between Chad’s heartbreak and that of all the other boys who would come through my life is that Chad quietly, subtly rejected me. I didn’t even see it coming.

Chad and I became friends slowly. I can’t remember exactly how we met, it was probably at school or through church. We did not attend the same churches so when he invited me to youth group, I said yes easily. I was happy to deviate from my current youth group if it meant time with a cute, Christian boy. Because we shared these same Christian values I assumed we were a perfect match. As a young teenager, I wasn’t prepared for a Christian boy to reject the Christian girl. We liked to hang out together, and I know we had a connection neither of us would say out loud. This is how good Christians date, I thought. It would be slow and romantic and Christ centered.

So when he started dating one of my friends, I was shocked. I couldn’t believe it. How had I misinterpreted all the signals? Hadn’t he felt the chemistry between us? How could something like that be one sided? What made it worse is that my friend was opposite from who I thought he would want to be with, opposite from who I was. She wasn’t a Christian, she was pretty, obnoxious and always made sure she was center of attention.

As a 13 year old girl I didn’t yet understand the complexity of wanting to be friends with some one and also being insanely jealous of them. That’s a different kind of heartbreak, I think.



What I know now is that was how my friend coped with the hard things in her life. She didn’t have two parents at home who provided for her and loved her as mine did. She didn’t have very much money and she didn’t live in a large, beautiful house, like I did. She liked to cuss and date all the boys and do the things boys liked her to do (or so the rumors said). Even back then I knew this wasn’t good or healthy behavior. Yet I couldn’t shake off my jealousy of her. Because she was so incredibly outgoing, cute, fun and willing to “put out” she constantly had attention from the boys. Including Chad. My Chad.

In the back of my mind, I think I knew introducing them was a bad idea. But, like today, I wanted all my friends to know each other so we could all always hang out together. Plus I trusted Chad somehow. I trusted that we were slowly becoming a couple. I wasn’t a huge flirt, being super self conscious and naive. I could not believe Chad wanted to be with her.

And just like that, I experienced my first heartbreak.

Watching them hold hands in the dark auditorium as we sang worship songs during youth group was torture. She wasn’t actually a Christian, had she told him she was? Or is it because she was the opposite of everything a Christian was supposed to be? I felt betrayed by him and manipulated by her. It seemed to me she was trying on this Christian hat as an experiment. But I was the real deal. I didn’t have to pretend. How could he not see that?

I don’t want to ever forget that experience of heartbreak. On one hand, it shaped how I would interact with boys in the future. Watching my friend get what I wanted taught me how to do the same thing. And I did. I performed very well in the years that followed. My behaviors led me to kiss boys I didn’t really want to kiss, date the boys my best friend liked and constantly be pushing past my own comforts in order to always be the one who would get the boy.

Now, on the other hand, I want to remember my brokenness and heartbreak over Chad so I can be more available when my daughter gets her own heart broken by another stupid boy. See, I didn’t really tell anyone how I felt, how sad I was. Instead I cried alone in my room night after night, feeling mortified for crying about a boy who was never even my boyfriend. I mean, I had to reconcile with the idea that he never did actually like me like I thought he did.

He liked my friend who was everything I wasn’t.

I don’t want my daughter to experience heart breaks like these alone. I don’t want her to feel like she has to change who she is to get what she wants. And so, as I work to remember what it was like to be a young person, I want to be able to give her what my mom could never give me: A safe space to talk about these things. Even now as my daughter will be 9 very soon, I make sure to give her time and space to tell me about her friends and all the cute boys while I listen. Just listen. I wanting her to feel validated in her feelings. There are times for me to offer advice, but it’s honestly not often. It seems that simply talking through what’s happening in her head leads her to the conclusion she is looking for.

So, Chadwick, you were the first boy to break my heart. At the same time, you showed me the qualities I wanted and found in Mr. Sexy: quiet, good and a Christian.

*Chad/wick is not the actual name.


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Jessica Biles

Jessica Biles is a leading expert on women’s sexual health and wellness in the Pacific Northwest. An award winning “sexpert”, it is her goal to help any woman enjoy a fulfilling and vibrant sex life. Jessica is highly recognized and endorsed as a trainer by the world’s leading sexual education company, Pure Romance. A 6-figure entrepreneur, she leveraged her sexual health thought leadership to earn a spot in the top 3% of her industry. An active member of her community, Jessica has worked with nonprofits like Open Arms Pregnancy Center and local area churches to bring attention to and demystify sexual intimacy issues. Jessica is on a mission to help women and couples have the important conversations to enjoy a better sex life.

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