Who/when was your worst heartbreak?

Question

Describe in detail who and when. What ended it? How far had you come into the relationship?

Lliam · Accepted Answer

I had had relationships with girlfriends since I was 16. In 1991, I was 37 and just out of a relationship. She was 34 or 35 and working at a place I went to fairly regularly for my job. I had always thought she was cute and quirky - short (5'2"), a halo of shoulder-length, light-blond, bouncy-curly hair, and big, blue eyes and glasses. She wore funny clothes at work. As it turned out, she bought complete outfits from a particular boutique. They included skirt or dress, jacket and accessories. And she ALWAYS wore heels of some sort. The outfits were attractive and she thought they were professional, but they were kind of bulky and not very sexy.

At some point, I asked if she'd like to go out to dinner. We made a date.

We had a pleasant date at a nice restaurant. Afterwards, I walked her the short distance to her rented house. We stood on the doorstep chatting for a couple of minutes. We said goodnight and she turned to go inside. She unlocked and opened the door, then turned, put her hands on top of my shoulders, rose up high on her tip toes, and gave me a kiss with lips so surprisingly tender that my head spun. I held her in my arms for a moment and then she went inside.

Petra and I started dating. As it turned out, she was a German national who had been brought to this country by her mom when she was an infant. She was not a U. S. citizen but had permanent residency.
Soon we were virtually living together, mostly at her place. We were inseparable for over a year. Her appearance matched every single aspect of my ideal woman. Plus, she was indescribably horny, uninhibited, orgasmic and adept. Her entire body was erogenous. So the sex was out of this world, but I also loved everything about her. She was tender hearted but also plucky and stubborn. She was no door mat, worked hard, and was determined to never give up in the face of adversity. She had a teen age son who lived out of state but who she met up with regularly. I guess that made her a MILF. LOL

At the end of our relationship she pushed me away. She was dealing with some deep issues. She had confided to me that her step father had continually molested her from the time she was about two years old until she reached puberty. She was seeing a councilor when we were together as she had been doing for many years. I think the trauma of her abuse contributed to a few things. One was her insatiable sex drive. Another was her inability to fully trust men and to push them away when things got too close. Another was her alcoholism. On a few occasions she had told me that she was an alcoholic but I didn't fully believe it because I never saw her drinking excessively. She was working to control her addiction and I wonder if her access to sex during our relationship served as a substitute for alcohol to some extent.

I can also acknowledge, from my current perspective of greater maturity and experience, that I was relatively clueless during the time we were together. I was immature and rather self-centered. I didn't have the tools to understand what Petra was going through or to help. I could be defensive and unable to open up completely or communicate clearly, myself.

thehorriblesheikh · Accepted Answer

I have only been in one relationship, which was supposed to be a friends with benefits thing that turned into a relationship. I was 14-15 years old and she was 19-20 years old. She looked cute and hot at the same time. I loved the bun she'd make with her hair. She was thick and curvy. She had a nice smile and a confident personality, I liked that. I asked for her number and that started our 2 month story of friendship, relationship, and heartbreak.

Our friendship was good, our relationship was dull, and the heartbreak was brutal. About 1 and a half months into the relationship, the problems began. I made the first mistake by not giving her the attention she needed and by being angry all the time. She would just take it and ignore it, responding with love and understanding afterwards. The nicer she became, the more I resented her, I think. Soon enough we started talking less and less and then I believe she thought I was cheating on her (I was not), because I was not giving her sexual attention. We broke up officially and decided to remain friends, and then she started ignoring me. I wasn't used to being ignored then, I was used to people doing me free favors and practically dying to be friends with me. I was the cool and popular kid. I lashed out on her and in my anger said things to her that made her cry. I threatened to rape her (I shouldn't have). Then I called her poor (which she actually was). I think it broke her into a million pieces. I kept trying to hurt her emotionally, and she kept taking it, not even using one bad word against me. Every now and then, a friend of hers would come to me and try and convince me to let her go, he went as far as "offering" me another girl. Time passed on, I started getting bored of her and moved on to other girls. I don't remember if I hurted her in any other way, I probably did. I never dated again because I realized dating wasn't for me because I don't feel the need to be loved, so why bother with dating.

The saddest thing in this is I guess, that I still feel no guilt for doing what I did to her. Even though I acknowledge what I did to her was wrong and I have been the kindest person to women ever since.

I know I'm a monster, and turns out I was like that to everyone and I had no idea. I was drunk with the praise I would get from others. I still get a lot of praise for various reasons. I think my friends and family always knew what I was, a sadistic piece of shit. Only my father didn't mind saying it to my face, though he's dead now. Good riddance to that religious fanatic, who hated me for rejecting his religion anyways.

Ultimately, I think I'm a product of the abuse I went through as a child, I think it damaged me in a way that cannot be fixed, perhaps.

Anonymous · Accepted Answer

I met a guy through a mutual friend in Jan 2020 and he told our friend that he was swept off his feet by me. That I was the kind of girl he always dreamed about etc etc.

He spent days looking for me on social media, and then he messaged me telling me about his feelings and intentions quickly. It would have to be a LDR so I said I liked him but no - (I had also just been hurt by a break up not long ago). He picked up the phone, called my family, and asked to marry me because he believed he could give me everything and he wanted us to live in the same country/together. I was swept off my feet, like my Prince Charming had finally come into my life...

2 days later I find out he had a girlfriend back at his country, and in fact they live together. Things got really messy and I said some things I shouldn't have. He ghosted me. I begged for him back/closure because I couldn't understand how someone who showed so much interest could have a whole other RS and ghost me like that. 2 months later he got in touch with me, promised me he was single, and agreed to be in a LDR with the intention of marriage later in the year/when we were both ready.

4 months into the LDR, I find out over social media that he is still with his girlfriend. I called him, wept on the phone and told him he had crushed and destroyed me. He begged for me to not break up with him and insisted we get married that very day to prove his loyalty. He said he only loved me and nobody else, and that girlfriend meant nothing to him. He also suggested I message his 'girlfriend' and talk to her myself as his wife, to prove his loyalty.

I blocked him. I am still emotionally damaged as this was 3 months ago but I am doing much better now. Overall, we were on and off for 8 months and I really loved the guy. I'd never been in love before like I was with him. Despite what it may seem like, we had a really strong connection and compatibility. I will never understand why he threw it all away like that. I was willing to give him my heart and more... just not my dignity.

Cherokeehp · Accepted Answer

That would have to be my ex. But unfortunately I kinda walked right into that heartbreak myself. I was obsessed with this guy in high school. I saw him my first day of senior year and I was absolutely smitten. We ended up becoming friends and then one day I told him I wanted to have sex with him. He ignored me. About two weeks later he gave me my first kiss, we ended up making out, and he asked me to be his girlfriend. I was a bit suspicious since he was way out of my league, but I said yes. We dated for a short while, he took my virginity, he dumped me right after, he told people I was a slut, got a new girlfriend, she threatened to beat me up, and then some other stuff happened resulting in him threatening to kill me. I wanted him to like me so badly. Now all I want to do is stomp his teeth in. It’s been a few years, but I don’t think I’ve ever hated anyone as much as I hate him. He claims to have just wanted sex, and I offered him no strings attached sex, but instead he chose to fuck with my feelings.

Paris13 · Answer

My First Love at 13-16... I broke it Off for He was Immature. Although we Were in Love, I thought it Best. Very heartbreaking. I didn't get Over him for 7 years. No matter who I had Dated and Mated. Years later, 6 Kids and Not What I Would Want. lolxx

jennifer_bloom · Answer

I think the last one hurt the most cause I was very lonely at the time and he was one of my only outlets for it

perfectchaos · Answer

The worst heartbreak was a girl about 3 years ago. She was my girlfriend at the time. Knew her for about 7 months and dated for about 4. I really loved her and we had a very deep emotional connection. Sexually though we were as deep as a puddle in death valley. I have a high sex drive. She had a super low one. She had no clue how much she was hurting me through the sexual deprivation. I could have made it if she didn't nearly tease me every day. I do mean about every day she would tease me. It boiled over one day because it started bleeding over into the emotional side. Like I never seen this talk about but the longer she neglected me the more I felt unloved and unwanted and I'm pretty sure it wasn't true. Anyway all the pent up tension led to multiple fights in a week time period. Our final fight basically ended with words that I didn't mean but I can never take them back now. I remember texting her maybe I'll find a girlfriend who will actually cuddle with me. I immediately regretted it afterwards. Before I could fix it she broke up with me and blocked me on everything. People who are on the outside and don't know me won't believe me but I believe everyone has to make their choices and I would never try to get someone back if they did not want to be with me even if I truly loved them. That being said I hate texting good byes and I made the mistake to try and break up with her face to face the right way. I was greeted by her dad who just said get lost she doesn't want to see me. I left on bad terms. I lost someone I truly loved and in the worst way possible. I have no clue what happened to her. She could be dead for all that I know.

TruthBringer · Answer

I was 20 when I had my first and most severe heartbreak. It was a LDR of 1.5 years and I fell in love with the idea I made her out to be, rather than what she actually was. Eventually I had to break up due to her lies, her ditching our meeting time for irrelevant events and disrespect + racism from her family side. Looking back, I'm glad I broke up. 99% of the relationship was about her. And it's like I was playing the personal therapist more than I was being a lover. Her mental health condition was badly affecting my mental health, and I had a temporary depression because of that relationship. I'm leaving out A LOT of details, but frankly, they are too much and way too many (bad) things have happened these 1.5 years. I used to be very energized before the relationship. I came out emotionally and mentally exhausted. Even the relationship after that one was no where near as tiring as my past LDR.

Now I'm in a healthy relationship with a lovely girl who not only knows how to be a good lover + teamplayer, but also has a loving family who never did me wrong infront or behind my back. Life is good when you ditch the wrong people out of your life.

answerseeker127 · Answer

Mine was pretty rough.

We started dating when we were 17/16 in highschool. We worked together, and we stopped seeing each other because she was also dating another guy at work.

We got abck together a few months later as an exclusive couple. During the summer, she ended things because of her religious beliefs and I wouldn't convert.

After a year of not talking, I reached out to her after a vivid dream I had of her. She said I hurt her and we couldn't get together again or be what we were. She said she didn't want me in her life anymore.

7 months later, she tracked me down on Instagram and asked to call me. She explained she got a message from the holy ghost to contact me. We talked for 5 hours that night, and for a few weeks we talked as friends and admitted we still had feelings. I told her I loved her and I thought that was gonna be it, but she said she refused to let me go again.

We dated for a while and had an amazing relationship. But she had already agreed to go on a mission for her church. I tried her church but I couldn't convert. She said I tried she will let our relationship work.
I asked her to Marry me and she said yes, but left on the mission.

A few months in she ended things. I tried to fix things a few months later and she gave me an ultimatum about converting.

I confronted her about it when she came home, and she lied about our relationship issues and blamed me for the relationship failing.

A few months later, I happened to drive past the Mormon temple and saw her getting married.

I didn't date for a few years. Barely have dated since.

Anonymous · Answer

I really liked this guy and he was giving off signals that he felt the same. we would face time like almost every day. He would always ask me who I liked, and one day I said to him that I liked him. He said that he liked someone else and I couldn't like him. luckily for me, I played it off as I was joking, so then he was like "haha" shortly after, I just couldn't keep it in, so in a cute way I told him I liked him. He said that he felt the same, and wasn't sure how I felt so claimed he liked someone else. 3 days after, he snap chatted me saying he had second thoughts. I thought he was pranking me. he said he was serious and he just wasn't really into me as much as he thought. I was devastated, he didn't really soften the blow either. I ended up crying that night but decided to stay friends ( dumb move) the whole time as friends he treated me like nothing. he constantly talked about hooking up with another girl and even sent me a photo of him hooking up with that girl, the day before my final exam. it got so bad to the point where I was so heartbroken, I broke down at a family dinner, in the middle of a conversation, and just cried. I never felt so unloved in my life. luckily my family comforted me so much that I couldn't have asked for anything more. my family made me realize out of self-respect, I needed to tell him to get lost ( so I did) because of him, as I was healing, I ended up going to a rebound who ended up being a predator. I was 16 and he was 20. he was a lifeguard so I thought I could trust him, but he ended up using that as a way to loore girls. he played so many mind games, and constantly kept pressuring me to go downtown with him (an hour drive) and he made it clear to me that I was the side chick. I broke it off with the rebound because my dad said to me " you look so sad, I wish I could stop it for you. what is it?" and that was a pivot point for me. it took me a year to recover from the heartbreaks. and today I am healthy, strong, and love myself!

Anonymous · Answer

My worst heartbreak was from someone I was never in a relationship with. We met my first year of college, a bit of a difficult time in my life so I wasn't looking to meet anyone. He struck up a conversation with me one day and then we began to talk every day for 2 semesters after that. We had so much in common and he was such a great guy, I truly thought that we would end up together.
Our last day of school was perfect. After class we got ice cream and took a walk through the park. I was hoping that he would ask me out or something because I didn't have the nerve to tell him how I felt. Instead he broke the news to me that he had been accepted into his dream school and would be transferring.
We eventually lost contact. There were times when my heart physically ached, it truly felt broken. Not telling him how I felt remains one of my biggest regrets. I had nothing to lose, especially when looking back I'm sure he felt the same.
He made me feel all of the cliche things; butterflies in my stomach, heart skipping a beat, smiling for no reason... I've yet to meet anyone that makes me feel the same way.

Bang5luts · Answer

I would have to say the relationship before my last one had to have been the worst heartbreak I think I've ever experienced.

My fiance and I had been together for 3 1/2 years. He sister had past away two days after my birthday. My fiance had put off plans to spend time with her sister to throw me an amazing birthday getaway. That weekend was the most romantic weekend I have ever experienced. She really spoiled me.

Anyways, he sister had past away while we were gone. I felt really bad. I mean it caught us off guard. Some times I have a tendency of accepting blame before it's placed. This is one of those times. I told my finance I was so very sorry for allowing her to take me out instead of spending time with her sister. It soon went down hill from there. My fiance started grieving and drinking heavily and we drifted apart.

Anyways, the break up caused me to experience severe anxiety where I felt like I couldn't breath. I felt like I was dying. Pervious to her sister dying my finace were inseparable. We were so deeply in love. We spent every minute we weren't working together loving our families and each other.

When we split my fiance ghosted me and I moved out.

We're really close now her and I, 5 years later and we try not to let the shadows of our past mistakes haunt us today or ruin our future friendship. She's still an amazing woman who has been there for me and my family even though we aren't together now.

DizzyDesii · Answer

Damn thats hard. My first ex hurt me by possibly getting my friend pregnant, but i dont remember crying about it. I prob cried more during the times he was mentally abusive and calling me the B word.
The second ex hurt me when he wasted my time. That shit is precious. I didn't even care so much about breaking up, i was just mad that i missed out on other things i couldve been doing rather than being dragged along by him.
The almost boyfriend between them prob hurt me the most. I dont think i ever cried so much. I found out he was talking to another girl. I also found out he was an ex porn star. I also found out he was selling nudes to gay men for rent money. Just so many things that traumatized me

sheikalana · Answer

I think I was 19 years old. We were in an on&off relationship for nearly two years. I loved him deeply but one day my best friend caught him with his now wife and I was devastated I cried so much for so many days and so many nights, suffered a lot. Me and my best friend confronted him and he denied everything. I was so traumatized that I didn't date or had sex with anyone in two/three years. After a few years I realized that that was one of the best things that happened to me. I've had a few other heartbreaks after but that one was the worst by far.

Anonymous · Answer

I cried the most when my first cat died.

a car tire ended it on 4th of July night when I wasn't home.
we spent 3 years together and was the first of death that was my responsibility and ownership.

I've had human relationships that were very painful but didn't cry as much. it's all hard. loss is hard. change is hard. discovering myself and my flaws is hard. Understanding people is hard. That's growth. When it gets easy, there's another challenge ahead usually... hopefully a nice plateau in life for a while and support through it.

No giant oak tree ever got to it's majestic stature without fighting its way out of the hard shell and through many cold nights and strong storms.

Syrian_survivor · Answer

You'd think it would be the 3-year long online relationship which ended in a disaster, but it wasn't, that actually did more good than harm in my life.
My worst heartbreak was my first relationship that only lasted 1 month when I was 15, at the time I was still growing so I thought there was something really wrong with me, she was my first love and I was so naive and foolish about all this love stuff, I didn't even understand why people would feel heartbreak and why they can't just easily let go
The love was strong, true, and passionate, at least from my side, I thought it was mutual all along, i thought others had my same level of love and emotion and i thought there love by itself was enough to keep the relationship strong and going, it all collapsed in a very quiet and very sad end, and her getting with another guy after 2 months (at least that's when she made it public), I was absolutely devastated.

ohshee · Answer

I pushed all of them do far back I don't remember I do remember it hurt and I do remember saying to myself I would never let another person in that far and I think now a days if I see something that's going wrong I can kinda feel it and I end or try to end them as friends no reason to hate each other

proteus912 · Answer

My worse heartbreak was a few years ago now. My boyfriend came to my place and we spent the day together. We got lunch and I showed him around my town seeing as he hasn't been there before. At the time I thought the day was good, but looking back there were signs that something was wrong. Then later that night he broke up with me over text and didn't even explain why. I pretty much cried for an entire week and to this day I still don't know what happened or what went wrong

Jjpayne · Answer

I have yet to experience a heart break. Probably the closest is waiting in loneliness for my relationship time to come. Which I'm hoping will be this year.

Just the feeling of never having a love I think can pretty close to losing a love because both are related to rejection in some degree.

AlexanderAnttila · Answer

My first girlfriend whom I was on and off with in gymnasium. We were going on 2 years approximately when she one day at her place callously told she didn't love me anymore in the middle of a conversation. I left instantly. That stung but it was the first and necessary lesson on love for me. Don't be too naive.

GoodGuyBreakingBad · Answer

My very first girlfriend ( ex), I bought her an engagement ring and within 5 days tell me that she wanted to break up with me so the engagement was also over as well I live in America and engagement is when a guy presents a girl with a ring before they get married which could last up to a year to two years, Usually, a girl never proposes to the guy but I imagine she could do so.

lanadelrey25 · Answer

The worst? When my grandfather never answered my letter begging for him to change his perverted ways, for the sake of our relationship. By not answering, he declared his absence of love for me, thus breaking my heart.

Anonymous · Answer

In juniorhigh i have a bestfriend and she have a cousin (Yohan) and so three of US really close. One day my bestfriend said that her cousin like's me and well... i kinda like him to so after that he keep me in the dark (you know how puppy love works right lol?) after 6 month with no the certainty of our relationship he dump me infront many of my classmate he said "stop told people that we are dating it's gross you damn lunatic" and after that we are Immortal enemy lmao

Anonymous · Answer

I dated a girl for 6 months when I was 19. I loved her and when she broke up with me I didn't want to get out of bed for a week. The only time I ever cried in my life was that week. But I didn't tell anyone how I felt because my family and friends don't talk about feelings. I never loved again. I have never been happy since. It has been 12 years and I still feel the pain when I think about her. Sorry for the downer but you asked.

Tomsta · Answer

First love, we never dated. She and her boyfriend knew how I felt about her and she still proceeded to use me as a emotional crutch. I deliberately avoided her ever since I realised I had these strong feelings for her; she was with someone else and avoiding her in person as my way of learning to accept that

Anonymous · Answer

I used to like/date this boy. I slipped up and said I loved him and everything (he said it back like twice) . About three months later he had one of his friends come and end things (of course I was kinda upset... probably would've been less upset if he did it himself) . Then the next week he was with someone else. So him liking her ended it and it was about like 7 months ago.

Anonymous · Answer

It was six years ago now, I was in love with a girl who I had known since I was seven. A mutual friend had invited her to their house where I was waiting to surprise her and tell her how I felt with a romantic gesture, I had heard rumours that she felt the same way about me, that i did about her. She never showed up, though. She ended up in a car crash on her way to me. She didn't survive it.

Anonymous · Answer

Truly, is a costant one. Even if she loves me and all, through no fault of her own I keep feeling worse and worse.

Sarah44444 · Answer

I ended my relationship December 2019 and the whole relationship was just horrible. He feel out of love with me 3 months in the relationship and then it just became abusive so I left after 7 months.

Slim57 · Answer

My ex, first love, thought I loved girls before her but I never did. All of it was fake by her to just say she never loved me at all after the last fight we had then she ghosted me not to mention in the meantime she was chatting up multiple other men.

Anonymous · Answer

A guy body shamed me, compare, chose and like other girls over me and everytime I see them I always remember that pain and hurt

Anonymous · Answer

After taking care while I'll... Cooking for days and other works... only got abuse mostly... Abusing if cooking were late for some time (even when you make multiple items ) and other... got called guys like you are good only after 30 and many abusive things from multiple girls 😑

Anonymous · Answer

Why does it matter to a girl who cheats on her boyfriend behind his back by giving a stranger guy her Snapchat because he was handsome?
You just wanna enjoy people's problem because you got payed back for your deeds.

clampfan101 · Answer

Here you go.

dudeinohio · Answer

My marriage of 17 years... my ex wife told me she wanted to separate.. I had to move out and start a new life over... very depressing.

Bluemax · Answer

My wife's death. We were married for 14 years, and would still be married today.

SoapySandwich · Answer

My girlfriend of 3 years passed away this year. haven't come close to feeling like this before.

navyrobin · Answer

All my heartbreaks have been due to me lying to the guy. I made a promise to myself to not get into another relationship if I’ll keep up this immature childish attitude.

jamesgoldman · Answer

King George V 9th March 2018  I had a funding problem  About 18 months together My relationships were amicable splits so this will have to do

Massageman · Answer

A gal I dated in Jr and Sr year of H. S.  We weren't quite to the point of going steady. College and a "dear john" letter kind of killed it. :- )

Anonymous · Answer

Two months ago, we have been together for a year and 2 months. he was my first love, I never loved someone like I loved him but i am now in my healing process.  People come and go!!

Static_In_The_Attic · Answer

My worst heartbreak was when the jokers at work took away the ice cream machine.

llcanon · Answer

My first Love. all the way back to 1975. It still hurts. i have never recaptured that love since. i have married 3 times and none comes close to my first love. High school sweetheart

scooogy · Answer

It was a female school mate on a class trip when she ended it like on the 2nd day because others made fun of her all the time, and I had to get through all that for another 3 days.

Tea-Spaghetti · Answer

Yes but what do you think about what I said about Norway culture, people, and society?

Twinrova · Answer

Are you still cheating on your boyfriend with that guy from the party? :D

IronmanT · Answer

13... when i was told for the second time in 3 months that I wasn't wanted and would never be a real part of the family.

H3xaD3x · Answer

A year ago, 8 months long one. we were even naming babies in that very short time. Turned out she was a catfish, a worse kind of one

Cowboy6666 · Answer

when she rejected me because i hadn't so much money also the other girl turned out to be racist n rude when i told her about my race

DayDreamingPHd · Answer

that was in 2010 when my ex went back to live with her mum since then I've stayed on my own now it's 2020 the end of it >

legalboxers · Answer

my ex from 5 months ago.. we were suppose to get married.. she ended it...

Anonymous · Answer

When my husband said you being fatty and make a diet for me with no pizza😭😭

Anonymous · Answer

the girl i loved turned into Sub Zero from Mortal Kombat, froze me along with my heart, and proceeded to perform a fatality move which left me in pieces.

AlongCameCindy · Answer

First heart break too me about 4 years to properly get over it, and another one in 2016 took me a few years too, they've all scarred me,

Soleil6996 · Answer

Ah... it was her disbelief paired with patents/others teaming up against it. My dad for simple reasons of wanting her for himself (fathers can be such bustards, yes, as can uncles and best friends)

Walrus_au · Answer

April 17 - 20 2015 Hoban James Dax about 35 weeks into the relationship Death ended it.

LEADFOOTboi · Answer

my last x... was the absolte worst... i had high hopes... we were together almost a year

Liam_Hayden · Answer

None. If a relationship ends then it isn't meant to be. I just move on.

Dave31989 · Answer

I've never experienced heartbreak. I've had girlfriend's but, never heartbreak

Nahid1707 · Answer

Heartbreaks and moving on is the worst part of any relationship

bobalife · Answer

It’s still something I’m working on forgiving...

Anonymous · Answer

Crazy maybe to you but I never had a who heartbreak more like a “it” heartbreak like experience wise

DavidFox · Answer

I tear up thinking about it..

collie22 · Answer

i still cry , i don't want to talk about it

Who/when was your worst heartbreak?

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What was your worst heartbreak?

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What was your worst heartbreak?

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