Anatomy of a Teenage Heartbreak

Hello friends! This is a blog topic that I have started to write so many times, with the first draft coming after an editor suggested it when my blog on First Love had been so popular. I have set it aside more times than I can count, adding a few things here and there, because I like to take those trips back in time to describe every emotion of events like this, and this one required a bit of research. I was unmotivated for the research part for quite some time, and so this has been set aside for years. (I was reluctant to explore my emotions written in my diary. Dredging up that misery was every bit as painful as I thought it would be due to the self-loathing described in my diary.)

In terms of writing to inspire or give hope, I sincerely wish this piece to add to the discussion for anyone going through a terrible time post love breakup. You will see a dedication at the end to some friends who are going through heartbreak right now.

Some may never experience love heartbreak, and some may experience it way too many times. Life isn’t always fair this way. Particularly for teenagers going through heartbreak, it is a scary time for very fragile and vulnerable individuals, which will be further elaborated on in this piece. Yet, time does heal as I discovered the hard way, and each new day brings a promise of better things ahead. That is the real message here.

For my own story, aside from a savant-like long term memory, I kept my diaries and the old love letters. I had to review my diaries from that time, which I kept all these years. Then when I finally decided to put all these thoughts together, I had to review a few of the love letters that you will see referenced in this piece. They are a necessary part of this true story, because it has to be understood how, at a mere age 15 and 16, I could have fallen so deeply in love. His love was written down, recorded on letters, and so you can see and understand how I could have trusted his words and promises of long term devotion, along with his fidelity, and monogamy though just a teen. It seems unlikely, and some may argue that it is impossible to have anything but puppy love at that age, but I assure you that at that time my heart was in it for the FOREVER. Perhaps without this element of the love letters and written swearing of love, devotion, and promises, I would not have fallen so far into a deep, deep well of love, that made climbing back out so torturous.

By the way, in love relationships, I have suffered exactly two crushing heartbreaks. I feel that I possessed a strength and a resilience that helped me get through both the first and second one without any noticeable long term damage. I have spent quite a bit of time nursing my friends through theirs so I know that serious depression can follow.

Note: I am only addressing my first heartbreak when I was a teen. For the second heartbreak, I was already a mature adult, a mom, with my self-esteem well intact. It made bouncing back that much easier. Don’t get me wrong, I still went through hell getting over it, but it wasn’t like the hopeless black hole of the first. There was no self-loathing at that time either.

When one is a teenager, there is no understanding of psychology, behavior, human nature; and trust is a large part of the innocence of youth. Self-esteem issues and hormones make even the smallest disappointments huge. A crushing blow like a break up is most dangerous at this vulnerable time. Due to those factors, it makes the heartbreak that much harder to understand and cope with in the aftermath.

When I was sixteen, I honestly thought I would die of a broken heart. If you want to read about the fantastic parts of my glorious first true love romance you can read this FIRST LOVE blog highlighted here for the whole story. I fell deeply in love with a boy one year older, and he wrote me daily love letters with the following quotes: (my editor also wanted me to write a blog or book with all the love letters in them – she was fascinated. They were that good.)

“I love you very much, and I dream about you at nights. You are really so fantastic and I love you with all my heart and soul.” “Since meeting you my life shall never be the same. I could never love another girl as much as I now love you.” “I think you are the most fantastic thing that has ever happened to me. My love for you has no limits and grows stronger daily. I could never, or that matter never want to, love another as I do you.” “I want you to know that my feelings about you are genuine. You always hear teenagers talking about love and romance. I feel that my love for you is more mature and sincere. I know for a fact that I really love you and I know the reasons for this love. It’s the real thing.” “What is life without your love? The answer to that question is unbearable.” ” I’ll always love you for the rest of my life.” “My love for you is eternal.” “My love for you has greatly matured into a strong passionate love. I love you as I have never loved anyone else. You are beautiful and perfect and I am comforted when you are by my side.” “I am grateful that you are mine, I will always love you.” “You have changed my life so drastically for the better, and there is not a second of the day that I’m not thinking of you. I love you so very much, I love you infinitely.”

Here are the best ones of all: “You completely enrapture me. As long as you want me, I will be faithful and loyal to you. You are wonderfully perfect.” And lastly, “Since I first met you, my mind is constantly preoccupied with images and thoughts of you. I never thought anyone would be able to affect my brain so drastically. I would be perfectly content to spend the rest of my life with you. If I lived to be 3 billion years old, I could never grow tired of you. I hope our romance continues forever, and I envision and dream of many great times together.”

Those words committed on paper had me believing him, trusting him, having faith in him and our relationship; and I so believed in our love that it seems that my entire world revolved around it. At the time, I was not a student of psychology, and did not comprehend the hormonally-driven fickle workings of the teenage male brain and heart. For me it was true love, and it was forever. Always an insecure girl, when I was with him, or reading his writings, my self-esteem began to blossom, just as my looks did at the same time.

The forever he spoke of only lasted until he went off to college, while I was still stuck in high school; and he found so many new pretty fish in the sea. Especially with the goading of his mom, who thought I was not “Good Enough”, he was itching to date others, especially one specific girl who pursued him. Our relationship was breaking down into monumental fights over his wish to be free. And then one day, a year into our romance, he made his move to break loose. He broke up with me over the phone. (I heard from mutual friends that he immediately started dating a girl at his college.) It was a blow so crushing, so overwhelming; and mixed with jealousy, and sometimes anger and rage. I was so easily disposed of AND replaced!

He went off and continued to live his life as he saw fit, and my entire world came crashing down into a cesspool of self-loathing and heartbreak. ***A movie that illustrates this kind of heartbreak in a very clever and visual manner, and one of my favorite movies, is “300 Days of Summer.” Highly recommend a viewing of this one.

I remember the emotions vividly to this day, feeling in the first days and weeks as if my heart was made of fragile china that went crashing down to the concrete floor, spewing remnants in every direction never to be gathered together again. I went into a depression immediately, a mind-set of bleakness, darkness, hopelessness, and losing my zest for life. Tears were a constant, my appetite was gone- and I was already a bit too skinny, and each morning I woke up to the unbearable pain of a new day without my true love. As I arose each day, the reality hit me of a large hole where my heart used to be, and with the knowledge that I had to plod on without him while he was having fun with another girl. I was jealous, and green with envy that he was with another, which compounded my feelings of being morose. I wasted millions of tears on him, and compulsively re-read his many love letters, with so many promises; to try and make sense of how someone could write those gorgeous words and give them only a temporary meaning. I asked over and over again in my diary, how could those words be lies? How could those words not not stay true? It was my senior year of high school, and I wasted about a month of that year in a hopeless and depressed state.

Fortunately, being my senior year with lots of activity as a girl who was involved in everything, and having a lot of friends that year who rallied around me, I began to emerge from the barely living. I have to say here that I would have benefited from having an adult to talk to or even a therapist, but there was no such thing for me to help me process these very complex adult emotions of true heartbreak. My friends tried to fix me up. I remember the first date after the breakup, some weeks later, and I had to go to a school event, so I reluctantly accepted a fix-up. I actually felt nauseous the entire date, and had to go home early so I could cry into my pillow. I was not yet ready to date.

This heartbreak seemed to last an eternity, but slowly I somehow forced myself to get together with friends, attended school events, and dated an understanding boy a few times. (And here I have to give a shout-out to my friend since this very era, Deba, who loves being mentioned in my blogs. He was a true friend, distracting me with a Grass Roots concert project, 3 x cards!!! but he was also the leaker of information on the new girl in my ex-boyfriend’s life. Although that news always brought me misery, I needed that information to get stronger and move on without him. Having no hope made me stronger to build a life without him in it.) My girlfriends were absolutely incredible as well. I am still friends with all of them today, despite my moving 1600 miles away, and they are all absolutely precious to me. They are all mentioned in my diary.

Two months after the break up, a great thing happened: I began working at the most fun place ever for a teen – a discount department store that employed a whole new sea of young boys my age and a bit older. The break lounge was more fun than it seemed possible at the time, and it was there that I re-learned the fine art of flirting. Less than three full months post break up, while still trying to glue together the tiny shards and pieces of my shattered heart, a fun-loving, blue-eyed Ivy-Leaguer caught my eye at work and flirted with me. And that’s when I knew my heart was truly on the mend, because when he flirted with me, this one special boy only, my heart felt those familiar flutters once again. I had pieced together enough of my heart to feel that pulsing and quickening as this guy rapidly became a major crush, and it was very mutual on his part. (He became my boyfriend a short while later and this great blog on him is linked.) At that time I also discovered there were plenty of fish in the sea!!!

When I outgrew my dependency on my first love, I saw that he did me a MAJOR favor; as dating others was fun and enjoyable, and those dates were some of the very best times of my young life. I appreciated the opportunity to learn and grow from those fantastic relationships I had while dating several boys. When I look back now, I can’t even imagine my college years without those great dating experiences.

Inevitably, once I began to really move on with my life, my first love came calling again, pursuing me again and again through the next years; (all documented via old letters) and since I retained some feelings of attachment and sentimental love, I dated him again while I dated others. It took more than two years for it to happen, but I finally let someone new invade my heart, and let myself fall in love with someone else.

Interestingly, the tables had turned, and he was the one on the receiving end of hurt and longing described by what he wrote in a few letters to me. In these last letters he informed me how hurt he was from “(my) scorn, and rejection, (of him) and of (his) heartbreak, and even shedding tears,” because I wouldn’t ever commit to him again. He had finally figured out my true worth, and he wanted me back, forever, or so he said in a new set of letters. The power had shifted though, and my power was in never letting him hurt me to this extent again. I eventually had to let him go for good. By this time in my life, Carole King’s song with the words, “It’s too late baby, now it’s too late, though we really did try to make it. Something inside has died and I can’t hide and I just can’t fake it,” partly describes why I couldn’t go back to him. For another, I never really trusted him or his beautiful words again, and told him so. The unwavering faith I had in him and what we had together in our relationship would never reappear, and I moved on to others. It was a protective device after a crushing heartbreak not to give my heart to someone who could not be trusted. (Note: a tiny sliver of my heart retained some love for him but that is always the case with a first love.)

This is well described in a song I adore about first love and heartbreak – Joan Baez’ “Diamonds and Rust.” It is hauntingly beautiful and whenever I hear it, it brings up these long buried emotions of my first love. It is true for me as it was for her in that how she is all the much wiser. Her ending line, “If you’re offering me diamonds and rust, I’ve already paid,” really says it all.

So many of us have already paid. We are survivors, we learn, we grow, we put one foot in front of the other and plod on and many times emerge better than ever. Again, the promise of tomorrow is that better days are coming.

I know this is way encyclopedia length long, but if it helps one person know that they WILL emerge from heartbreak, given time, then it was worth it. Dedicated to my friends Frani and to Mary Jane.


  • I thought I was the only one who obsessed on Joan Baez’s incredibly powerful line, “Our breath comes out in white clouds-, mingles, and hangs in the air. Speaking strictly for me, we both could have died then and there.”

    • Janet, I am obsessed with every line in that powerful song, and as a matter of fact, the line you mention I relate to in a very strong way, as it is a true Romeo and Juliet line – and I am totally obsessed with that movie. You and me both!

  • Have to give you a compliment here- though many artists put their heartbreak into song, and many artists put it into other forms of media, I have never read it in this format quite like this before. Good job in sharing your pain as an artist!

    • Case, this is one of the highest compliments I could get because you so understand my motives as an artist. No one thinks twice when they hear a song of heartbreak, or see a movie of heartbreak, but other than in novels, it is rarely described in autobiographical format like this one. It was difficult to go back and see the words in my diary of self-loathing and self-blame in particular, so I have suffered for my art!! Thank you for reading and understanding, and taking the time to write in. So appreciated!

  • I have an identical story. Weird to see how common this must have been for so many.

  • Have never seen it described like this before, but I am a male and have been on the receiving end. All the truth.

  • I am going through this right now!! Your description is so accurate- sometime I wonder if I will ever smile and have fun again. How long does this awful pain last?

  • Thank you for this- you poured out your emotions- May I contact you?

  • I read this and so related! When I lost my love, I kept singing a song by Skeeter Davis/ End of the World!!! Have a listen!!!

  • Self-loathing is a key part of this read for me- my daughter’s is over the top thanks to her ex. Help!

    • Yes, and that is exactly why I was reluctant to open up the diaries from that time. I was so hard on myself to the point of being cruel and self-defeating. Not a healthy way to be. I suggest a therapist, I truly believe in them and my daughter practices in this field and sees the difference it can make in a troubled person. Will email you further information.

  • It is 10 times worse for our girls now- their former Love is plastered all over Instagram and Facebook with the new girl. How do you get over it when it is in your face? My daughter is suffering!

  • “I’ve already paid.” Best line. Haven’t we all?

  • Found this on our mom’s site- Thank you! So many of our girls think it is the end of the world during heartbreak- we need more survival stories like this!!

    • I got a similar reaction when I posted my own Mean Girls story. I am so glad I finally put this together and hope it helps give perspective. Thanks for reading.

  • Thank you for posting this important blog to our mom’s group! My daughter is going through this right now. She reads her boyfriend’s texts and emails over and over and asks me why he lied to her. How do I explain? I read her your blog and she thought it was written about her. Of course her “love” is off with another girl already. I am sharing this with all the moms I know- it is that important that our girls know their misery is temporary!

    • Please hug your daughter for me. I know what she is going through and I care. It is temporary but seems the end of all things at the time. Please help her hang in there through this rough patch.

  • Sent you a private email message as this one hit home with me and was something I hadn’t thought of in many years. So many things you said reminded me of my own situation where my self esteem plummeted. Thanks for publishing this, I plan to share it around, especially to teenage girls who might benefit from hearing your story of surviving this crushing blow. Nowadays with social media exacerbating the problem, so many girls are seriously at risk of self-harm and other extreme behaviors. As you can tell, I work in Mental Health. This is a great read. Thanks again.

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