FLASHBACK FRIDAY: 10 Lessons from 10 Romantic Relationships



It’s no secret that I’ve had more than my fair share of romances and heartbreaks. In fact I knew this blog post could get pretty lengthy if I talked about everything I’ve learned from my previous relationships so I’ve pre-emptively written part 1.

You see from meaningless flings, casual flirtations to full blown romances, there’s always something to learn from them. Whether your relationship ended with a happy ending or it crashed and burned like a tragic tale, there’s always some kind of good you can find in the bad, and words of wisdom for the future.

Depending on how you look at it, I’ve been somewhat unlucky in the love department, I’ve been through a lot of heartbreak situations and each time I’ve always ended up wondering what went wrong even though now having had time to evaluate those situations I can clearly see all the mistakes I myself made in those relationships. I either loved too much, didn’t love enough, the timings were wrong or the person wasn’t right. For one reason or another it didn’t work out and so I want to impart some lessons I learned in my previous relationships that I believe helped me find the love of my life and gain a new appreciation for learning how to love without getting hurt.

  1. Voldemort
    You have to value yourself otherwise they won’t value you.

Voldemort was my first boyfriend in high school. My friends and I call him Voldemort because once we broke up we all agreed we would never speak of him again. So Voldemort was basically my first biggest crush. I actually cried more about him than I have ever cried over a guy. I was so young and naïve and literally would walk till the ends of the Earth for him. He was in a band, which I thought was so freaking, cool. He played this angst-ridden teen that was living an oppressed life even though he lived with his two middle classed parents in a good-sized house in a very nice neighborhood. Even by teenage standards he was quite a bad boyfriend, he would break up with me every week or whenever he had a gig, and despite this, I would still go and watch him at his shows being super supportive and just pretending not to look when he flirted with other girls. Voldemort made a huge point of making sure I knew he was attractive to other girls. I remember on my birthday he said he wrote a song for me when he played it for me, my stupid heart melted, then one day I surprised him at one of his gigs and I heard him tell the crowd he had written a song for a special girl. I was surprised that he knew I was in the crowd when he barely ever noticed me enter a room, but I was even more surprised when I saw him playing it to another girl with that same sadly sappy look on her face as I did. Voldemort almost always had a reason why he needed space from me, and when he wasn’t making up an excuse, he’d be flirting with my best friends, hanging out one on one with one of my girlfriends and posting pictures with them online when he told me he was sick, or flirting with girls on his band page making bets as to who was willing to buy him a pint for breaking up with me. Prom had to be a pretty low point for me. Despite how much of a flirt and ‘wannabe playboy’ Voldemort was, he never had much game. We were pretty much in our longest stage of our relationship when Prom night came, I was so happy we were going to be going together, despite him being my date he pretty much spent the entire night with other people and barely smiled for the photos we took together. Eventually, the night ended and we went back to his. I was a naïve little virgin and I was desperate to lose my virginity like everyone else was, I thought we were on the same page and he seemed pretty into in. Then as we were kissing he sent me home. As in he actually told me to go home, no goodbyes or anything. Nice. Anyway, you’ll be surprised to know this kind of relationship continued for about 3 years, he kept me wrapped around his little finger like a little puppy, believing him each and every time he told me he loved me. He would treat me however badly he wanted to but as soon as he saw me pulling away he would tell me what I wanted to hear and I would excuse everything bad he had done previously. He acted like an asshole because I let him act like an asshole, especially to me. In fact, I loved him more for it and convinced myself that he was just a broken boy needing my love to fix him. He didn’t, he just needed me for his ego. Once he broke my heart for the final time I actually realized what I was doing wrong. I didn’t respect or love myself enough to know my worth because I didn’t know my worth I let someone give it to me, I let someone tell me what I was worth. I didn’t respect me, so there was no reason for me to ask him to, and as a result, I was treated badly and he knew he could get away with it. Unfortunately, it would be many years before I actually learned what self-worth meant and by then I was already so broken that it took a lot of work to make me feel worthy again.

  1. Neal

Sometimes it can seem perfect, but it’s just not meant to be.

Neal was my first proper relationship, my first boyfriend, and regrettably my first love. I don’t say that because I regret the relationship, read all of my love letters after the relationship, I really don’t regret it, it’s just that I hated everything that happened when the relationship started to fall apart. A lot about me changed when we broke up, some for the good, some for the bad. I went through a really dark time. You see of everyone I have ever known, loved and been with, Neal was the only one who really understood me, got me, clicked with me. We were so similar and we bounced off of each other so well. Our relationship was like a fairy tale up until we started to fall apart. In fact the only problems we really ever had was to do with other people rather than between us. Everything was perfect or so we thought. Being young we were convinced we were going to be together forever, I realize now how unrealistic that expectation was. We still had a lot of things to learn, we had a lot to experience and go through. Whilst the relationship seemed perfect it just wasn’t the right time. I learned a lot from being with Neal, how to love unconditionally, how to fight for what was important, how to be silly and not take life so seriously but also how to love yourself enough to let go when you know something is no longer meant for you. We loved each other so much that we continued to fight even when it was no longer right. We lost each other and ourselves in the process and it became too painful to be right. The most important thing I learned was how to give up, because even if it is what you think you need, what you want, sometimes it’s just not meant to be.

  1. Shaun

Good friends doesn’t necessarily mean good boyfriend.

Shaun and I were very good friends, at one point I actually considered him as one of my very best friends. He was one of the few that helped me pick up the pieces of my broken heart when Neal and I broke up. He rallied beside me to try to bring me back to my old self. I confided in him a lot of the dark things that I was feeling; he was my shoulder to lean on. I never thought I could feel love again after Neal; in fact I was convinced I didn’t deserve love. Shaun made me believe in myself again, he tried his all to bring me out of my sadness and showed me that love was possible even in the darkest of times. Somewhere between hanging out like we normally did and talking late at night when none of us could sleep, the line between friendship and romance became blurred. I was only looking for a good time and Shaun thought he was looking for love. I wasn’t ready, I just couldn’t bring myself to put my heart through something so traumatic as love again, but Shaun persisted, he was convinced that because we made such good friends it meant we would know how to be the best partner to each other. It took some time to convince me but eventually I came around to the idea of us dating. Shaun was perhaps someone I would class as being one of the most painful relationships I went through in my teenage years because of the level of betrayal I felt. He spent more time trying to convince me to love him than we did actually spend loving each other. Shaun hurt me in so many ways that only a friend can. I trusted him not to mess me around like other people did. I had told him that once we crossed the line from friendship to relationship we wouldn’t be able to go back to the way things were, I know he truly believed our relationship would be different, but it wasn’t. Whilst Shaun loved the idea of being in love he had to admit he was not in love with me, whilst I was a good companion for having fun with, he just couldn’t see a future with me, he didn’t think about this when he was telling my Mother how he was going to take care of me, he didn’t think about his wavering love for me when he made plans for our future, he never once considered his emotions as being superficial when he told me that I could trust him. Maybe it was because I just wasn’t ready, maybe it was because Shaun was as inexperienced as I was, maybe there were too many things going against us but eventually that fantasy of a happy relationship began the end of our beautiful friendship. Shaun taught me that just because someone is a good friend doesn’t mean they will be automatically make a good boyfriend. The truth is there are so many other factors to consider, of course being friends with someone you’re dating is a huge bonus but that fact alone just means that you have a higher expectation of them and when the relationship ends, you’ve got so much more to loose and it hurts just that much deeper.

  1. Tyrone

You can’t force yourself to love someone.

Tyrone was another good friend of mine; he was such a good friend that I could not consider him as anything more than that. I loved him deeply like he was my brother and cared about his wellbeing. He loved me too; unfortunately it was just in a way I could not reciprocate. He spent years pining after me and even though I knew this, I never acted on it. We had been through too much and we were too close for me to allow romance to ruin such a great friendship. The problem was no one else saw it that way. On a daily basis I would have friends and acquaintances tell me how they felt sorry for Tyrone, how I strung him along like a heartless bitch and no matter how many times I protested that I didn’t want to loose him as a friend, people thought it was just because I liked the attention. The thing was Tyrone was one of very few guys who I actually felt comfortable with, call it crazy but I actually wanted to have at least one good guy friend who didn’t try to get into my pants and Tyrone seemed like the only guy who actually respected women enough not to force himself on to them. Eventually it reached a point where a friend of mine said ‘Jessy, you’ll lose him if you don’t give him a chance, there’s no harm in trying and at least if it doesn’t work out, Tyrone will know it’s not meant to be and you can go back to being friends.’ After what happened with Shaun I just had no hope but I figured it was better to try than loose Ty altogether. So one day I accepted his offer when he asked me on a date, and we went, he was a perfect gentleman, at the end of the date he kissed me on the cheek and took me to my taxi. We continued to date for a few more weeks but I just never changed in how I felt towards him. I don’t know if he thought I was falling in love with him or not but he seemed so surprise when I didn’t share any romantic feelings for him. I couldn’t even bring myself to kiss him or hold his hand. I explained to him that I just had no romantic feelings for him, he seemed hurt by this but we continued to see each other. Call me naïve but I just assumed we were going back to being friends, I went to a party one weekend and ended up ‘hanging out’ with another guy, this got back to Ty and he accused me of cheating on him. My god was that a terrible time, I got a reputation for cheating, like I was this conniving bitch who went around breaking people’s hearts and cheating on them. Ty and I didn’t speak for several years after that, then one day a chance encounter lead to us become close friends again. A few years ago we got into a big argument about something completely unrelated, we stopped speaking and the last I heard he’s actually in a really happy relationship with one of my ex-boyfriends. So the moral of the story is you cannot force love, if you don’t feel anything for someone you have to be honest with yourself and with them, pity dating someone doesn’t make you a good person and telling them the truth about your lack of reciprocated love doesn’t make you a bad person either.

  1. Leon

Being afraid of someone is a big sign you should leave them.

Leon was this big man in the city who both intimidated and excited me. I’d never dated an older guy before, sure I’d fucked plenty of ‘old’ guys before, but never actually dated them. Leon was a leader by his own right and being his girlfriend made me feel like I was his first lady. Sure I was his first lady but after the relationship ended I found out it didn’t mean I was his only lady. Leon was a strong person in the community, everyone knew him, he was well liked, hell he would be the main host at a party that he wasn’t even throwing. Everyone liked Leon and because I was Leon’s girlfriend, everyone liked me. He would call me his Queen and he’d write songs about me, he loved me, I know that much but the way he treated me would say something completely different. At a petite 5’1 and wearing size 8 clothing, Leon would pull at my love handles and tell me I was fat, he would then drive me to the gym and insist I work out for an hour, at the time I thought this was good because I played netball and was a cheerleader so I believed he kept me fit. He would also make me stay at home with my family if he wasn’t around, to make sure I was abiding by his rules he would make me take pictures with my family and send it to him so he knew I wasn’t lying. Once I went out for dinner with friends 2 nights in a row, both to celebrate a friends birthday and he spent an hour shouting at me telling me how he didn’t want a girlfriend who was looked cheap and acted like a hooker, he also said that I disrespected my family and that I was disgusting. Every time his treatment of me would become too much I would threaten to leave him but he would retaliate by telling me that no one liked me and that my friends were only with me because they wanted him, he convinced me that if I left him I would have no-one. One night he told me that if I ever left him I would never be able to show my face in the city again. Leon’s threats never got physical; it was the insinuation that shook me the most. It took a long time for me to realize that I was afraid of him. I was so afraid to be with him but I was also scared to loose him, his threats weren’t just if I left him though, it also included things like ‘if I get bored of you and break up with you, you’ll be left with nothing’ or ‘if you get too fat I’ll break up with you and no-one will want you because no-one likes to fuck whales’ with or without him I figured my life was over. I don’t actually know what the final point was for me but one day I woke up and found that I had become so emotionally numb that his threats no longer made me feel anything. I turned my phone off, smashed it to pieces (how fucked up was I?) I just took myself off the grid, and eventually forgot I was even with him, 2 years of the hell he put me through and it was like this cloud covered me, there was no relief no happiness, there was no sadness either, it was just over. Eventually it made it back to me that he told everybody I was crazy and he had to cut me off. Everyone believed him, everyone pretty much abandoned me, but his threats had had me so prepared that I just didn’t care. I learned from that day on that being afraid of your significant other is such a deal breaker and that it isn’t normal or healthy to live in fear when you’re in that relationship. No amount love is worth living in fear for your life and the depression that they insist you surround yourself with. Show yourself the love that they are incapable of giving you.

  1. Drew

Just because you’re a nice girl doesn’t mean you can’t hurt nice guys.

I met Drew at a club when I was totally hammered. Picture this, all my friends are all sitting on this very long (wall length) sofa, they’re all with their guys and girls, making out and I’m the only one dancing, I mean there were other people dancing on the dance floor but I was on my own dancing. I took one look at my friends and decided I wanted to make out with someone too, so I turned to the first guy I saw and pulled him to the sofa and began to make out with him. That guy was Drew and he actually turned out to be a really nice person. We dated for a while and we got to know each other really well. The thing was he had a really complicated job that meant he had to be out of the country for 6 months of the year. He seemed really lonely because of his job but his career aspirations required him to follow through with his contract. Drew was the first guy I met who ever had a good future to look forward to and he wanted me to be a part of it. During the early stages of our relationship he kept things very open, honest but at the same time made it clear he was not looking for someone to just have fun with. The thing was there was quite an age difference between us, whilst I was still so ready to go out every night, get drunk and have fun, Drew was planning his future, he was looking to buy a house and settle down. I tried so hard to make myself get to his level; I never really understood what an intelligent, handsome and head screwed on guy ever saw in me. I was such a careless and cut loose kind of person that I couldn’t even imagine having a steady boyfriend let alone playing housewife to someone who wasn’t going to be around for 6 months at a time. I could have really loved Drew (side note, I do talk about our relationship in more detail in another blog post, stayed tuned for that) but it was just not the right time, I wasn’t ready to give up my freedom especially not at my age. He was such a nice guy; a genuinely friendly and loving person who I know would have looked after me. Whilst he never expressed his disappointment in me, he let me get away with a lot of things I know hurt him. I think my pent up anger from previous relationships were taken out on him and it wasn’t fair. He let me flirt with other guys right to his face, I could go out with him, leave him all night but he’d still be waiting for me at the end of the night with the taxi. Despite him getting his happy ending (Find out more in my Blog post – when it goes live I will link it to this post!) I still regret hurting him. You see I never considered myself a bad girl back then, but what I didn’t realize was that just because I was a good girl didn’t mean I couldn’t hurt a good guy.

  1. Freddie
    Pain is temporary.

I’ve been laughing about what to call the lesson I’ve learned from this guy but the truth is he was just an asshole who fucked and went out with my best friend whilst he was fucking and going out with me. So what did I learn from this relationship? Maybe we can figure this out with a little backstory. Basically I met Freddie when I was just trying to be single and mingle rather than find a relationship. He was not on the same page as me and was convinced he loved me. When I refused to become an official couple he told me I would regret it and that I had hurt him like no other girl had before. We didn’t talk for another 6 months but when we did we formed a close friendship, we were good friends and I stupidly thought I fell in love with him. We dated, some weird things happened between us, I was dating another guy at the time but I was not emotionally with him, things between Freddie and I escalated until we slept together. I realized that our friendship was becoming something more so I confided to a friend about my worries and how I was feeling. I go through this in more detail on this blog post:


Eventually I found out that whilst I was dating and fucking Freddie, he was also dating and fucking my best friend. You know like the nice guy he was he then proceeded to accuse me of ruining their relationship. Thinking about what happened I would like to say that I learned that once an asshole always an asshole but that would be the words of a bitter woman who is still not over it. But honestly I am long over it, not because I understand why they did what they did but because I just don’t care anymore, at the time it was the worst thing to have happened to me, I felt like I was going to die because the whole thing was a massive mind fuck and even though I was the one they hurt, people seemed to sympathized with the Romeo and Juliet couple, as if they were star crossed lovers, really they were just two horny people who got kicks off of sleeping with other people too, I somehow just got in the middle of it. I’m glad they put me through so much pain for a 3-month relationship. Really the thing I learned from this relationship is that everything is temporary, that pain you’re feeling, the sadness? Well it will pass, it won’t last and you’ll be better for it because one day you’ll wake up, your heart won’t hurt anymore and you’ll know that if you could get through pain like that then you’ll get through the other things too.

  1. Xander
    If he likes you enough to sleep with you, then he should like you enough to respect you.

Xander was just a random guy I ended up spending way too much time with. I mean that in the nicest way. He was my friend with benefits and we had this unspoken agreement that if we were horny and hadn’t met anyone after a night out we would go home with each other. It was a purely physical agreement and no emotions were meant to be involved. I was fine with this but for a while he was convinced I wanted something more, I think he was quite naïve, he didn’t realize that girls were capable of having as great a sexual appetite as guys could. He thought my frequent booty calls was me trying to pin him down and marry him, eventually his inability to understand what a booty call or friends with benefits was actually about both frustrated and annoyed me so I began to make new ‘friends’ and this did not go to well with him. You see whilst he was happy bringing home any type of girl to bed, he didn’t like knowing that one of the girls he was sleeping with (me) was also doing the same. He didn’t like that I had more game than him (I say that like it’s something to be proud of but I actually am deeply ashamed of my immature teenage behavior). Soon he would throw tantrums or start fights with him, if I got upset or responded to them he would accuse me of trying to ‘wife’ him and would ignore me. At one point I had a friend pull me aside and tell me that they felt sorry for Xander, that they didn’t like how I was treating him and that I should be more careful bringing home guys because they were doing their best to keep it away from Xander, so he wouldn’t find out. The whole thing confused me because according to Xander I was the one trying to trap him into a relationship and that he was repulsed by it. Xander was not courteous during this time and I made the mistake of continuing to sleep with him. Sometimes he would use emotional games to get me into bed but it was always on his terms, I could never call him for sex without being accused of tricking him. From this ‘relationship’ I learned that if he likes you enough to have sex with you then he should like you enough to respect you.

  1. Billy
    It won’t work if two people aren’t willing to try.

Billy will forever be in my memory as the could have been but never was guy who slipped through my fingers. I have nothing horrible to say about Billy. I may have a few harsh but true observations but everything I feel and think about Billy and our relationship has been played out in 3 very long letters to him, find part 1 here:


What happened between us was beautifully poetic and tragic at the same time. It was the typical love story where a guy and girl fall in love but are both in such different places in their life, somehow whatever they do, they keep going back to each other, both completely unaware of how the other feels. Each time one of them decides to take the step into admitting their true feelings for the other, something happens, this keeps happening until they both give up and convince themselves that the other one doesn’t feel the same way, all the while the audience is screaming, just say you love each other!!! Billy gave me great, memorable moments to keep with me forever, he also put me through hurt and sorrow and the truly frustrating thing was, he had no idea. He didn’t realize that by being loving and kind and romantic with me he was killing my very being. I’d question his kind actions then how he could quickly become cold. One minute he would be so considerate then I wouldn’t see him for days upon days. He would make me feel like he needed to be around me but then he would be insensitive, and never was it targeted at me, I was just too sensitive to take myself away from the situation. Billy and I had such strong feelings for each other but we played games as if we were both scared of being rejected by the other. I know personally I was afraid to loose his friendship but at the same time I loved him. Our frustrations over being unable to say how we truly felt ended up with us fighting about something completely random. We had plenty of opportunities to tell the other how we felt, we sure shared enough nights or moments alone when one of us could have spoken about our feelings and there were times when it felt like we would finally talk about it. It just never happened then, there was never a convenient time. The closest time we got to talk about romantic feelings was when we were drunk or high. We had an almost talk about how we felt for each other when it was already too late. I was in a relationship at this point and he admitted that he thought he had feelings for me, but what did he expect me to do, leave a great and loving guy for feelings he ‘thought’ he had? Whilst I knew that that word ‘thought’ was used as filler, I knew at that point he did love me; it was just a little too late. He could have said something sooner, back when we both had the opportunity to see where these ‘thoughts’ could go, the thing is whilst I was angry at him for not acting sooner, I should have also been angry at myself for not acting either. I learned in the hardest way that things don’t work out if two people aren’t willing to take a risk together.

  1. Norbert
    No matter what you’ve gone through you can’t hold it against every person you love.

Norbert (Norbert is obviously not his real name but we got into an argument when we were deciding his fake name and he kept pissing me off so I told him I was fed with his ridiculous suggestions for names and would give him the most weird name he’d suggested, my apologies for anyone actually called Norbert). He is my partner and my best friend. I owe a lot to Norbert for what he has taught me, about love, life and myself. I could write a lot about him but as this is over 5,000 words already so I won’t. I’ll put simply that our relationship is not perfect and is a continuous work in progress. What worked for us 2 years ago does not work now and we’re continually trying to find a new routine for our relationship. We’re learning and changing and it’s so wonderful to be able to grow with someone. There’s something comforting about watching the world change around you but knowing that the person you love is right beside you watching it change too. Norbert taught me how to love without having to hurt in the process, he taught me how to have faith in others, how to trust in myself and how to allow myself to be happy. He taught me I deserved forgiveness and showed me how to find my own fairy tale story. He taught me how to empathize, how to cry, how to feel safe. The hardest thing we had to learn together was how to let go of the past. Norbert had to deal with a lot of the bad things that people had done to me in the past. He faced the result of years of pain and abandonment when he himself had done nothing wrong. It was hard for him and it was unfair for me to expect him to do that, especially by himself. Norbert’s biggest lesson for me so far has been to free myself from the baggage of the past. He taught me that just because I had been through hell and back in relationship did not give me the right to punish him for it. Because the truth is you’re going to meet some assholes in this world, there are going to be assholes who know their assholes and they’re a lost cause, then there are assholes who don’t realize they’re ass holes and they’re so much worse. There are going to be people who are going to hurt you and leave you but there are also ones who are going to love you unconditionally and want to stay. There are going to be people who have good intentions but end up disappointing you and others who come along and suddenly become a huge part of your life. You need to be able to embrace each and every person who will come to you because each person has a story to tell and a lesson you will learn from them. Some are good, some are bad, but each one will leave you with something to think about. Every experience is being given to you to strengthen you and prepare you for later life, be thankful you have the opportunity to overcome these obstacles and that you have people to share this with. Remember that each of these romantic relationship lessons can be put together to give you one big lesson, everything is temporary but that doesn’t mean we should take anything for granted, be grateful for the learning opportunities and when things works out just know it’s because you’ve earned it.

Remember that whilst we need to take care of our hearts it’s also stronger than we realize. Love truly, and open your heart to the possibility of a new experience.

Do something to make your parents proud today, your kids proud someday but most importantly, you proud every day!

Peace and Love

Jessy x


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