27 Men And Women Reveal The Excruciating Details Of Their Most Heartbreaking Relationships

@krissana_renae / www.twenty20.com
@krissana_renae / www.twenty20.com

1. Engaged Three Months

I met Stephanie at a party in 2004, and we were together for 7 years. It was perfect, she was the love of my life. I asked her to marry me and she said yes. She was my best friend, my partner in crime, my teammate, my soul mate. We even had a dog. We were engaged only 3 months when Stephanie was murdered by an unstable person at her job at a mental health facility. Enter hell on earth. Now all I have left in my life is our dog, Dutch, the dog that probably saved my life.


2. Supportive Wife

Sticking by and supporting my husband of 7 years through his depression & alcoholism…only to have him tell me tonight he is leaving me. Pretty heartbroken.


3. The Best You Can Is Good, Good Enough

Knowing that my best wasn’t good enough.


4. She Disappeared And The Reason Why Was Crushing

I engaged in a long distance relationship when I was 15. Though several states away, we managed to talk several times a day, every day. Her name was Sara and she was the first girl I ever told, “I love you.” Through countless phone cards and several months (I remember making a big deal of our 6th month), we spent would talk for hours at a time, just laughing at the stupid stuff we would say. One day the inevitable happened and Sara broke up with me. She cited several vague reasons and I finally asked if there was someone else. She said there was, which I found comforting. At least there was someone to be there with her like I couldn’t.

Heartbroken, but consoled, I told her she was welcome to call me any time she wanted. Two months and as many conversations with her later, she calls me. I’ll always remember it. My family and I were eating dinner and my mom answered the phone. She looked at me and said “It’s Sara.” I was a little shocked and excused myself from the table. I ran around the house to find a chord-less that worked and took it upstairs. I hadn’t spoken to her in at least a month and was anxious to hear what she had to say. When I picked up and my mom hung up on the other end, I could hear that she was crying. She told me that she was in the final stages of her battle with leukemia. There was no other boy, she told me, she had only wanted to spare me the experience of losing her. She explained very little, just that she wanted to talk to me again and say goodbye. After hanging up the phone I just sat there and cried.

I’m 24 now and I still have trouble dealing with this. I have no idea what actually happened because I couldn’t get a hold of anyone at the number or the address. It’s possible that she was just trying to sever contact with me by feinting a terminal illness (sounds like a bad sitcom now that I say it), but to 15 year old me she died in a bed and I couldn’t be there for her. My imagination was consumed with the feeling of loss. To this day, I can’t watch A Walk To Remember. Fuck that shit. It’s 6 in the morning and I’ve just gotten off of work 2 hours prior. I’ve had a couple of beers and under any other circumstances I wouldn’t have shared this story. For some reason I thought it would be therapeutic. It wasn’t really.


5. In Love With Amanda

When I was 14 I fell in love with my best friend Amanda. We were together 24-7. We were adorable, we’d never leave each others side. A few years pass and we get a call that her mother had overdosed and passed away. We were 16 and my parents let her stay with us. We planned out our entire life together, we were going to move when we were 18 get married and have kids, we were going to be together forever. Well….that did not happen. It was the day after her 18th birthday…..I got a nice room at a hotel in Reno and figured we could walk around and see everything (we were from a small town). My mom decided that we could take her car and we started the long drive.

About 3 hours into the drive I got rear ended on the free way..the car spun out side ways and the front driver side slammed into a ditch causing the car to comletely flip. I didn’t have a seat belt on and went out the back passenger window. I woke up…there was dust everywhere…I didn’t see her. I look back and see the car upside down and tires still spinning. I ran over and crawled back into the car and tried to get her to wake up. There was blood and broken glass everywhere, I can still smell and taste the dust of the airbag and the blood in my mouth. She never moved….I layed there by her side until I passed out….I woke back up in the hospital with everyone around me. They kept having to push me down and tell me not to move. I had to find her I had to know she was ok. No one would answer me they told me to stay calm that I had fractured my skull and I needed to be still. They gave me a shot and I was out.

Four days later I woke up I could barely move. Thats when my parents came in and told me…she had died right then and there in the car. The first response team told my parents that I had been found inside the car holding her hand. I have prayed every night since then (3 years ago but it feels like yesterday) for god to give her back to me. To this day I know that it wasn’t my fault but I still can’t come to terms with it. I lost more than a girlfriend that day. I lost part of my own life along with her.


6. From Two Different Faiths

My boyfriend & I broke up over religion. We were in a relationship for 4 years and a couple of months ago, both his parents (who are Jewish), and my parents (who are Hindu), made us break up with each other because both families believed that there was no future for both of us.

His Jewish parents didn’t want a Hindu daughter- in- law and my parents felt the same about him. Although we had tried for the past 4 years to get our parents to accept the other, they never did, which always led to arguments.

We continue to remain friends now & it breaks my heart everytime I see him because I still love him immensely.


7. His First Crush

When I started high school…I went from one private school to another across town. I didn’t know anyone, and was pretty alone. Didn’t have any friends, and I wasn’t making any fast.

Anyhow, I walked into my home room class, and saw this absolutely stunning girl across the room. She had this auburn hair that was impossible not to admire. The teacher started assigning seats, and sure enough…he puts her right next to me.

I was such an awkward kid, I had no hope that I would ever say more than a word to her. Homeroom was a 15 minute period of announcements and socializing, though. It took her all of 30 seconds to introduce herself to me.

Every day, I would look forward to that 15 minute period in which all I would do is sit and talk to this bright-eyed beauty. She was my first real “crush” I’d say..and it became pretty apparent that the feeling was mutual. Most days she would grab my hand as soon as I sat down and write some sort of flirty nonsense on it. I loved every second of it.

Before I knew it, the homecoming dance was approaching. I’d never been to a dance like that, certainly never asked a girl to a dance, but I made up my mind…I was going to take this girl. Every day, I’d walk into that short period of my day, determined I would ask her to the dance. And every day, I’d chicken out.

Then, one day, she asked me who I was going with. I said I didn’t know yet, and asked he who she was going with. She told me about some other guy who asked her that morning. I felt entirely defeated, but I figured it was a lesson learned…a mistake I would never make again.

But, that date she went on turned into another date, and then into a relationship. She ended up spending the rest of the year dating that guy.

The next year, my dad was laid off and I had to go off to public school. I did much better in that school, I found a group of friends the first day. I also had a few girls chasing after me, so I must have grown into myself a bit.

I still had a lot of friends in private school, and I went to the homecoming dance at that school the following year. She was there, and my heart stopped in its tracks when I saw her. She ran up to me, gave me a big hug…and we spent a good part of the night dancing together. She was single again, and came to the dance on her own as well. I wasn’t sure what to make of it, but I figured I would be sure to get her phone number or something, and maybe get together with her.

Toward the end of the night, though…she went to talk to some friends and I went with mine. I turned around, she was gone. No idea where.

A few weeks later, a friend of mine told me that she’d asked about me. But by then, one of the girls who was chasing me had caught me, and I’d be in that relationship for a solid two years.

Three years later…I’m single again and in college.

I’m driving down the freeway in a snowstorm with a friend, and a car spins out in front of me, flipping into the ditch. I stop to go see if the driver is OK and call for help. As I walk up to the car, I see that bright auburn hair that stopped my heart four years earlier, draped over the steering wheel.

Sure enough, it was her. I know that since this is a “heartbreaking” thread, you’ve probably got an idea of where this is going…but don’t worry, you’re wrong. She came too as soon as I walked up, and it turned out she wasn’t hurt too bad. She had a concussion, and a few bumps and bruises, but altogether not in bad shape. I helped her out of her car and she came and sat with me in mine while we waited for the cops/ambulance to come. We talked a little bit, she was in a bit of a daze. Then, the ambulance showed up, the whisked her away and before I knew it, I was standing in the snow by myself, then telling a state trooper what happened.

I didn’t see her for another two years. The next time, it was in a grocery store. I saw her, and immediately noticed a gigantic diamond on her finger. For whatever reason, I didn’t say anything to her that time.

We’d run into each other maybe 4 or 5 years later, both of us with babies in our arms.

Nothing ever happened between us, and I know it’s not as bad as it could be. It’s more of a story of what felt like fate constantly pushing two people together, and nature/circumstance pushing them apart.

And while I don’t regret where my life has gone, I’ll always wonder what would have happened if I would have mustered up the courage to ask her to that dance.


8. “As Perfect As Heartbreak Could Be”

We dated for over a year and were each other’s best friends, we completely understand each other, and we are still madly in love with each other, but it was best for us to break up because we weren’t in the same place. She’s 20 and wants to be married and have kids soon and I’m 21 and wanted to date her for a while and get married and have kids around age 30.

It was mutual and we both knew it was best for us so we decided on day to break up. On the last day of our relationship I decided to take her out on one last date night. We spent the entire date thinking back and talking about favorite times together, things we’ll miss about each other, how we’ve affected each other’s life in so many good ways. I bought her flowers, took her to a nice romantic restuarant with live music, and went to see The Hobbit through all of which we held hands. It was one of the most perfect, romantic, happy, and yet heartbreaking date we ever had.

At the end of the night, we said our goodbyes as we hugged and kissed passionately for one last time and went our seperate ways, never to see each other again. It was the hardest thing I’ve had to do to this date, but I wouldn’t want it to end any other way. It was as perfect as a heartbreak could be.


9. Losing Any Chance

Developing a crippling mental illness in front of the girl I had a crush on over a period of about 4 years.

I went through 4 years of treatment at the local psychiatric clinic, various doses and flavours of anti-psychotic drugs, but due to a lack of an apparent “thought disorder” never received a diagnosis. That is to say I suffered and still do suffer auditory hallucinations and my inner monologue is not my own voice but the voices of others saying things to and about me but I was and am not “deceived” by it I guess is how I’d put it. It’s the difference between a person who sees aliens everywhere and believes that they are there and a person who sees aliens everywhere and knows he is hallucinating. It’s probably something like schizoaffective disorder.

It took me 3 years just to train myself not to react physically. When I say react physically I don’t mean talking to them I mean not bashing my skull and begging for it to end or having severe twitches because of immense frustration. It’s like being constantly tormented by something that you can’t ever avoid.


10. Losing Touch But Not Losing Love

Some years ago now back in school there was a beautiful, lovely and kind girl in the year above me who for some reason I don’t think I can ever fathom took a shine to me

We started hanging out a bit and talking a lot and I was infatuated with her, we ended up getting romantically involved. She was the first girl i ever really cared about, I lost my virginity to her and although the relationship eventually fizzled out we would still talk loads for some time after

Fast forward a year or two and we hadn’t spoken for a while. I come in from a nights drinking and decide to see what she was up to on Facebook

She’d died in a car crash because of a drunk driver the day before and i found out in a stupor at 2am on a Saturday and proceeded to bawl my eyes out till the morning.

As we hadn’t spoken for a while I thought it inappropriate to go to the funeral.

Still think about her sometimes but it’s a tough story to tell people so i just mainly keep it to myself


11. A Shattering Betrayal

I had a bit of a thing for this girl, lets call her Caitlin because that’s her name, for over a year back in school. I used to speak to her whenever I could, I’d help her with her English homework, sit next to her on the bus etc. The typical teenage romance crap.

Caitlin and I both had a liking for this local band who had made it relatively big, so, for her birthday I got two tickets to see them at a homecoming show as a way of asking her out. I put the tickets in her card and wrote some crap about looking forward to taking her.

Her birthday comes around, I give her the card, watch her open it, get a hug and a massive thank you etc, but that was about it. Meh, didn’t think too much of the lack of comments regarding the “asking out” part.

Concert day rolls around, I text her asking when she wants to get pick up. She doesn’t understand what I mean, tells me she’s already on her way there with *****.

Turns out she went with another guy, they started dating for a year or two.


12. Being Told This

“you deserve better.”


13. Too Late

Not asking her out, then after she moved away having her say “I loved you to.”


14. Never Forgotten

I was 16 and had just gotten my license, was in a great relationship with a wonderful girl of the same age. Her name was Emily. We were on our way to the movies to catch a late show, when crossing through an intersection we were t-boned on the passenger side of the car. Her side of the car. She was killed instantly… And I survived… I still wonder how and why I survived. Why was she taken at such an early stage in life? I’ve moved on since then, but I’ve never forgotten her.


15. An Unsettling Feeling

Met a girl at work. Not really interested in her, but she was cool. She was troubled a bit, but I didn’t know this. She gets my number, I get hers, she kinda blows me off. Never calls me, but we text a few times.

Anyway, she contacts me a month later, after I’d blown her off for Halloween, and she asked me if we could hang out b/c she’d been depressed lately. I said sure and thought this could be cool. She comes to my work to meet up with me and she’s talking guy problems. I’m like “wtf”, but I listen.

We get to my house, watch some movies. Hours later, we’re making out. We hook up, date for 2 years. I meet her friends, family, all that. However, along the way, she says she’s got this “unsettling” feeling. Not sure wtf, but w/e, I try talking about it, not much explanation. She doesn’t even really understand it. So I eventually propose, she doesn’t seem that excited, I come home one night, 3 months after our engagement, she and all her shit is fucking gone.


16. An Autumn Summer

A whole summer gives new meaning to life. You had few months of perfect, until the day he had to leave. I love you, I love you too, you cry, he drives away to the airport, and you know you’ll see him again. It’s autumn and the flamingos fly to another county too. 3500 miles away, but you talk every day. You miss him so much, it’s pathetic, every evening you leave the light on, what if he comes, what if he’ll knock at the door, what if… Winter’s not too bad, and he begs “You have to come and see me”, you trust him, and you say fuck it, why not! You buy a plane ticket from the little money you’ve got, pack your stuff, leave your job and tell your boss and friends “I’ll be back”.

They’re all gobsmacked, but everyone else are the last thing you think about. The airport has new rules, no smoking; in the cafeteria you have a coffee and not one but few cigarettes before the flight. Plane’s always late. 5 hours and you’re there, finally embrace him so dearly. You feel you’ve waited so long for this, and yet you have a month to show him just how much you want to spend the rest of you life with him. He knows it. It’s Christmas, it’s New Years Eve, with his family, but you feel left out, because it’s not your family, no matter how much they try to make you feel like home. The month’s over, you tried, no actually you haven’t, you didn’t know what to do, neither did he. It’s your last night together, and this time he holds you so tight and sais “Maybe I’m getting old, but I wish I could hold you like this forever”. You’re silent, your heart has found “home” finally.

Outside it is snowing and you haven’t seen snow in years. At Heathrow busy, people, you cry, let’s say goodbye, let’s pretend we’ll see each other again. On the plane you cry the entire flight. Back in Cyprus, it’s warmer, you’re broke, you spend the last money on the cheapest cigarettes, have one until someone’s picking you up from the new rules non smoking airport. You’re at home, but you don’t want to ever spend one day here alone. You feel sick, you feel tired, lonely, depressed, you cry again so much you throw up. Finally sleep falls over you heavy. It’s morning and it’s brighter today. Welcome back but heartbroken, friends see the sadness in your eyes, you pretend everything’s fine, get your job back, some money, you can’t eat, you unpack, and every day’s the same: work, home, cry, sleep, time forms a pattern and part of it is you writing like mad and writing and writing.

One day you get the phone call you’ve dreaded the day for it, at the other end someone’s telling you “I’m giving up, I can’t go on like this, it’s too painful , I have to give up, you know the reasons”, “but I love you”… well it doesn’t matter anymore. And it’s the day the whole world collapses, everything inside you turns inside out, upside down. You wish you die, but you’re too confused and don’t know how to do it, so you give up on that too. You’re still sleeping alone in your home, you don’t want to go there, but it’s where you end up every night. In the dark the radio plays the same song as every other night, and whatever song it is, it’s a love song and they’re all about you two that used to be, but aren’t anymore.

April, your birthday, presents, friends, everything, everyone. One thing missing, so you dial a number, a voice you love to hear and maybe for the last time. Stomach butterflies. You talk about small things and then you forget what you want to say and fall silent, just listen. Not words, but a voice. You’re happy he’s OK. Few tears and you hung up; the best present you got that day or any other day. So much to miss him yet somehow keep that special place in your heart for him.


17. It Wasn’t Me

Fell in love with a guy. In an attempt to get closer to him, we became best friends. I fell harder and harder in love with him. We shared everything; went on trips together, he taught me how to change the oil on my car, I introduced him to some great books/movies/music.

I watched him marry the girl of his dreams. It wasn’t me.


18. Looking Back And Seeing How You Screwed It All Up

Knowing that it was my fault we split up.

A few years back, I was in a comfortable relationship with a girl we shall call C. Been together for over a year and a half, but then things started going wrong. I used to get really annoyed that she never came out, all she did was complain, and then get in a mood when I complained.

Eventually, enough became enough, and we split at the start of September 2007. It was at this point the truth started to become clear.

The reason she never came out, is that I never invited her out.

The reason she seemed to always complain, is because I rarely listened (something I still do now)

The reason she used to get upset when I complained, is that by the end it seemed to be all I did.

In short, it was my fault that the relationship ended.

About a month and a half previous to these events, my best friend had moved to live in my parents house with me, while we finished organising, and we waited for the house to be ready. During this time, my relationship with my girlfriend became very one-sided. I never made the effort to call her or text her anymore, we’d only see each other at most 2 times a week, when we only lived 10 minutes walk away from one another. My reasoning for this was that “I’m spending time with David, sorry.” That was my answer almost every day, even when he wasn’t there (Don’t ask why, I still don’t know).

I was under stress at the time, but it’s no excuse (Was lining up to get my first house away from my parents)

At this time, an old internet friend of hers started to flirt with her again, it wasn’t something that ever bothered me, he lived in America, and didn’t stand a chance with her. However, there was one major difference between me and him. He was there for her, I wasn’t. I only found out that they were talking again through a mutual friend who didn’t want us to split.

When I heard, I decided to take a chance, and went up to her house with a bunch of flowers, to try to show that I could still be a good boyfriend. For that day, I was. However, the next day, things just went back to the way they were before.

We lasted just shy of another 3 weeks, which made things a little difficult as we were organising a panto together, which was uncomfortable for a while.


19. Did She Get My Ring Or Her Own?

Hearing my enlisted fiance married someone else when he was supposed to be in the field for exercises. Insult to injury: His mother was the one to tell me when I called her about some wedding plans. He and I were friends for six years before we started dating, “best friends” according to him.

I have been told about his wife, who seems near prefect and she has posted about “I married my best friend.” They knew each other less than a month prior to the marriage. I always wonder if she has the ring he said was for me or did she get her own?


20. She Was Once A Woman I Felt very passionate about

She went through what therapists later described as a “quarter life crisis” and experienced a psychotic break, tried to kill herself, spent some time in the hospital, went batshit crazy, refused treatment, won’t admit she is sick, parents won’t help, started exhibiting other manic / BPD behavior, compulsive eating, got all fat … I hung in there for a year, but there was an “incident” in front of … all my friends … where she ended up trashing our entire house, breaking anything made of glass, all the plates, my computer, her computer (which I paid for), injured the pets … man you name it.

I hung on for a year, I did my best. We begged her parents (mom was a social worker for fuck’s sake!) to help. Nothing worked. I failed. My best friend is out there, broken, sick, unhappy, experiencing the world through a veil of lunacy and dysfunction.

Hurts me to think about it. What a waste. Once she was a beautiful, smart, lovely woman whom I felt very passionate about.


21. It Could Have Ended Differently

My girlfriend and I had been together for two years. We lived together for a year, then I got a new job and moved 6 hours away for the second year. That definitely wasn’t good for our relationship, and we were fighting a lot towards the end. So, the last day I texted her (Monday), she told me she was going to a sorority event (she was pledging a pre-law sorority), so I said “Okay, have fun.” Her last response was “Thanks.”

The next day (Tuesday), no response from her when I asked how it went. I thought nothing of it, and even thought maybe they had taken her phone during the pledge process. However, her mom texted me that night and asked if I had heard from her, which didn’t sit right with me. The next morning, she didn’t show up to work, and that’s when I called the police. It was only then that I found out that she didn’t come home Monday night as well as Tuesday night. I was at work that day, and I couldn’t focus at all. I had no idea what had happened to her or where she was. Her phone was dead, and the police couldn’t trace it (they could only trace the last cell tower she was near).

I felt so helpless being six hours away. I was in constant contact with her mom and sister. They were putting up fliers, I was putting up pleas for help on Facebook, Twitter, etc. The next day, I didn’t go to work and spent the whole day on the phone with family, friends, police, anyone that I could think of. Everything went through my head. She was kidnapped, she was in a car accident. Everything but suicide.

Finally, I get a call from her sister Thursday night. They found her in her car two towns over in the middle of a field, and she had lit a gas grill in the back of her car and died from carbon monoxide poisoning. I was all alone hearing this news. I called my parents, and they couldn’t even understand me. This was the worst night of my life. I flew home the next morning and stayed there until the funeral.

Now, the story doesn’t end there. As soon as I get home, my dad tells me that he heard from the officer he talked to that my girlfriend was sleeping with someone I thought was my friend. I had no idea what to feel. Sadness, anger, disappointment? I felt like I still couldn’t be mad at her. I even called the guy, and I told him that there’s nothing I could say to make him feel any worse than he already does. He had a fiance, and she had already moved out.

I think the fact that my girlfriend knew she could never actually be with him was the last straw for her. But here’s the worst part. SHE TOLD HIM WHAT SHE WAS GOING TO DO THE DAY BEFORE SHE DID IT. We got her cell phone back, and read through their last messages, and she told him. She didn’t say where or when, but he still didn’t tell anyone. He basically said nice knowing you. I called him back, and he said he was “too drunk” to remember. Meanwhile, he had just driven home. I told him to not come to the funeral, because I didn’t know what my friends or family would do if they saw him. I haven’t heard from him since.

That was 13 months ago. I have a great group of friends and family that have been so supportive over the past year. I still talk to her mom weekly, and I still think about her every day. There are still some tough days, but I feel like having a daily routine has helped me get to a better place than I was at.


22. I Loved Everything About Her

My ex of 7 years left me, we had been best friends since she was 14 and I was 13, now her 26 and me 24. She met new friends, wanted to stay out late and I became the “suffocating, abusive” boyfriend that just wanted her to stop lying to me.

That’s seriously all I wanted, because she did. The day she left she hit me. She made plans to get a boob job, started dressing trashy and started hanging out with people at a restaurant/bar she used to work at. She left me, her stuff, our animals, everything.

That’s not sad, that’s typical bitchy girl stuff. Here’s what got me in the feels:

So I’m going through my stuff. Not her stuff, I had packed up her stuff for her. I come across a box with some VHS tapes, and as I go through it, I come across one labeled “Missouri 95/Oregon 96”. I know exactly what it is, it’s a family movie her family made years ago. I asked to see her when she was a kid, and she contacted them to send it over. What I didn’t explain is that my ex had a fucked up childhood, and has ran from literally every familial relationship in her life, so contacting them was a big deal.

I remember being so anxious about watching it: I never liked her family. But then I remember watching the video, and it panning to her, this beautiful little quiet tomboy, skin so dark from a summer tan, reddish-brunette hair and the most adorable smile I’d ever seen. That was Oregon. In Missouri (she was 10, summer of 96), she was a pretty little girl, still tan, sitting eagerly for a birthday dress being made by her grandmother. She was beautiful in a way I could never describe: so quiet and reserved, but sweet, curious, genuine.

These are just the memories of me watching it. I remember watching it and falling for her in a way I never could have considered. I now loved everything about this girl’s life, I realized it then, when I looked at her in that video.

I don’t know what broke my heart more, the fact that my ex left that tape without even considering or remembering its existence, or the idea that I was so bad, that she’d rather lose the tape and part of her childhood if it meant getting rid of me completely. I’ve considered sending it to her, but I don’t have her address or new phone number, because she refused to give them to me.

I’m getting over her, just not the shit she put my through, and I don’t think I can ever trust anyone again.


23. He Thought Only Of Her

Fell for one girl that lived in another city. Chatted and used cam every day and she knew my feelings towards her and I thought she had the same. Visited her as often as I could. This was going on for 6-7 months. One day she came home from a trip and told me that she fell for another guy and that she is sorry. I felt horrible but tried to show her that everything is alright. Talked to her about him and I even talked to him about her. Told her that she needs to tell him her feelings and to get out with him and do stuff. They both got together after i talked with her for nearly 4 weeks. It really hurt… But he lived near her and he could be there for her every day.

I talked to her for 3 more months and she told me how fine everything is and how sweet he is… At some point it hurt so horribly that i cut the contact to her. I told her what was going on in my head and stopped everything.

Never talked to her again. Still sad for me to think back. Even after 5 years.


24. My First In Every Possible Way

I’ve always been a…passionate person. This is a nice way of saying I am emotionally retarded and unable to aim or work my feelings in any proper sort of way. I had spent my entire romantic life leading up towards my Sophomore year of High School desperate for love, male or female. I had (and still have) some serious issues.

Then I meet Shannon. Shannon is a thick, beautiful, amazing, broken girl, and we identify on so many levels. Where I spent the years before longing for any chance at love, she took every chance. Her list of ex’s, male and female, was more vast then than mine is even now, 8 years later. She filled her loneliness with sex and hope and I just identified with her longing so much. We were best friends for a long while, but eventually I was emboldened in a way I never would be again. I became forward and she was very accommodating.

Shannon was my first in every possible way. Sexually, emotionally, just everything. She made me a better person, but she couldn’t fix me. I was so insecure, so broken, so afraid of losing this incredible, amazing thing, and after two and a half years of just struggling and trying and failing, it all fell apart. We were toxic for each other, and everyone seemed to know it. Both of our sets of parents refused to allow us to be together, so there was almost entirely sneaking around. School ended, she went off to college and I didn’t, and I was left behind.

Today, Shannon is a lesbian, and I’ve been living life as a gay male ever since. I can’t form any kind of meaningful relationship. Everything I do I compare to her and it’s just terrible. I’ve dedicated my entire life to just loving myself, so maybe some day I can be less broken for someone else, but I really don’t believe it’s possible. I live in her shadow, and I’m sure she never even thinks of me anymore.

Shannon, wherever you are, I still love you so very, very much.


25. She Didn’t Give Me Butterflies, She Gave Me Pterodactyls

My Freshman year of high school. (I hate telling this story but I didn’t go to work today so I might as well tell it) It was the middle of June, I was at my best friend’s graduation party. All of his family was there, a bunch of people from school, and of course I am too. I’m shooting the shit with some of his uncles or whatever and I happened to glance away from the group, and a girl caught my eye. There were attractive girls there, but nothing like her. Making eye contact with her took my breath away. You know how people say they get butterflies? She didn’t give me butterflies, she gave me pterodactyls. I walked over to her and introduced myself. It turns out she’s my friends cousin, he walks over and does the whole “Oh I see you’ve met Jessica”.

All I’m interested in is her. We start talking and we don’t stop. At first a couple awkward minutes go by but then our conversation gets flowing. Hours pass by in the blink of an eye and it’s time for her to leave. I get her number and text her. We talked until the next day that night, neither of us went to bed. A week later, we went on a date. And guess what I did. Classic Schmoesby. I told her I loved her. She said she loves me too. We hugged goodbye and we started talking more. A few days after our first date my band was playing a set at a local cafe, she came out and had a good time.

This became a regular thing, I would pull her on stage and serenade her and she would smile and cry and whatever. Then softball started for her, and I went to her games and cheered for her team. This went on for the 2 best months of my life.

Then it happened. My band was playing a set on a Wednesday night. She couldn’t make it because her sister had to work and her parents didn’t want to drive her (She lived 20-30 minutes away) I didn’t mind, it was just whatever. Well, She just told me she couldn’t make it to surprise me. We’re in the middle of a song and the stage manager runs up on stage and hands me a phone. We stop playing and he says “Dude. Emergency” I’m pretty pissed off until I take the phone.

It’s her mother. They were at a red light, the light turned green, and a semi T-boned them on the passenger side. Jessica took most of the impact and is being flown to a hospital ~45 minutes away. I’m bawling my eyes out and I don’t know what to say. The stage manager and I hop in his car and rush to the hospital. When we get there, she’s in surgery. I pace around the waiting room while we wait. an hour goes by then a few more.

Nine hours after we got there, she’s out of surgery and for the most part stable. I go and sit in her room by her side. All of her family’s there with me, nobody is saying a word. I grab her hand and I take a knee and start praying. I’ve never been really religious but her family was and I respected that.

For the next 48 hours I sat by her side holding her hand, feeling her gentle heartbeat struggle to hold on. She moves a little bit and makes a little bit of noise…she’s conscious. I can’t help but smile and tear up at the same time. She starts to tear up too. What came out of her mouth next are words I’m never going to forget. “Garrett, I love you. But I don’t know if I can do this.” My heart dropped, I knew she wanted to let go but I never want to lose her ever. I can’t believe what I’m about to say. “I love you too. And no matter what happens here, you’ll always be with me. Forever and always.”

Now we’re both bawling uncontrollably. I kissed her one last time and held her hand for another 22 hours. Every moment of which is burned into my memory. Listening to her suffer is one of the worst thoughts I could imagine, I still have nightmares about it 6 years later. Needless to say, she passed away. Since then, I have dated other girls but none of them have been able to live up to where she set the bar.


26. Her Last Words Still Haunt Me

I was 18 and I met Sandra who I think was my soul mate. I’ve never felt so connected to anyone before or since. We dated for over 2 1/2 years, and during that time we laughed and loved and cried together. When I think back about the best times of my life I usually think about those days.

But I was an arrogant ass and when things got a little stagnant I dumped her and began dating another girl. The new girl and I dated for a couple of months but during that time Sandra and I still got together. The day after Christmas I went for a coffee with Sandra and we confessed to each other how much we still loved and missed one another. We discussed marriage. She forgave my arrogance and said we could work on our relationship. It was amazing of her. I promised to call her the next day. On the 27th I tried calling all day but got no answer. I must have called 30 or 40 times that day. I worked night shift and when I got to work I tried calling again. At 1am I finally got hold of her. She was panting and sounded odd, and she told me to “fuck off and stop calling me, I’m sick”. She then hung up on me. I called back and her mother picked up and her mother also told me to stop phoning. She died at 2:58 am of meningococcal meningitis. I cried for 3 days non stop after that happened. I am 40 now and I still think of her every single day.

I’m glad I called because I think my phone call is what got her mother out of bed to be with her. The worst thing about it is that the last words I remember her saying to me were to fuck off.


27. He Was Living A Double Life

My boyfriend and I who were together for just over 2 years (we are gay, and we were young, so that’s a lifetime!)

We got together when I had come out of an abusive relationship, so this guy, let’s call him Dave, really supported me and helped me get my shit together. He was the first and last person I ever felt “I love this guy so much!”

About a year and a half in, he started modelling for extra cash, which is fair enough.

Everything was perfect, we had such a good relationship.

To cut a long story short, eventually he confessed that he cheated on me probably about…five times throughout the relationship. Then, one evening, a friend linked me to a Gay Porn site with the words, “You should see this…”

I clicked, and lo and behold, Dave’s modeling was actually porn. I had no idea. I can’t describe the feelings when I saw that website, I went light-headed as though I was going to faint. I numbly just walked out of the house and went to a pub, phoning a close friend with “Drinks, now.”

So yeah, that sucked. I genuinely thought he was “the one” and I even had considered proposing to him (ah, the folly of youth.)

To add insult to injury, he was really supportive of me when I spent time in a Psych Ward, when a lot of people had turned their back against me because of it. It was a pretty heavy mind-fuck…to be with someone so supportive and caring whilst…being like that behind my back.

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