Failed Relationships Will Eventually Lead You To 'The One'

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Status: Finished  |  Genre: Editorial and Opinion  |  House: Booksie Classic
My dating experience and what I learned from each.

Submitted: November 21, 2013

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Submitted: November 21, 2013




Names have changed. Stories remain the same.


This all begins when I was 16. I might have been young, but to me this relationship was as real as any.

The moment I met him I felt flutters in my stomach. It was at a rooftop bar-b-q that both our families had been invited to. Apparently, his aunt was one of my mother’s childhood best friends. My cousins and him were the only people our age there, so we ended up speaking all night. Before we left, he handed me a crumbled piece of paper in which he had jotted down his MSN messenger screen name. This was 2006. As soon as I got home, I rushed to my laptop and added him. I nervously waited for him to accept, which he did that very night. He sent me a message and we spoke continuously for weeks.

Finally, we went out on an actual date, dinner and a movie. At that age, I was going through a ‘punk/emo’ phase and Alfonso could only be described as preppy. I loved it, It felt rebellious which only fueled my attraction to him. It didn’t hurt that he played the guitar and had his own car.

Eventually he became my first ever boyfriend. Five months into our relationship, I pull him aside at one of the local underground shows. I let him know that I loved him, but we had to break up. To this day, I have no idea why I did it. I was still immensely attracted to him, but being the curious teenager I was, I started feeling restless and curious what would happen if I ended things. This is the first time I ever saw a boy cry over me. I didn’t know what else to do other than hug and kiss him. The relationship was over that night.

Of course, Karma decided to show her face. The next day I regretted my decision. I think I was just testing the waters and didn’t really believe the relationship was going to end. I called him asking if we could forget everything I said. He declined. This is when things got bad. I started obsessing over him. I would constantly drunk text/call/myspace and eventually Facebook him. I felt like such an idiot for ending a good thing. This went all the way through my freshmen year of college. By that time we had already been broken up for over a year. I honestly wouldn’t blame him if he still thinks I’m crazy.

To this day I still think of him. He seems happy now and has a beautiful girlfriend, which is great. Sometimes I still wonder if he’s the one that got away. They say you never forget your first love right?


Alfonso taught me to be mature. Because of him I realized my actions have consequences. Relationships consist of two very real people and playing with someone's feelings will never end well.




Then came Federico. I met him during Freshmen orientation at a college in Florida. He was a Sophomore. Coincidentally, we were from the same hometown and had a few mutual friends back home. Remember, during this time I still thought I was ‘in love’ with Alfonso. Federico was nice to me. More than nice, I could tell he was falling in love with me. I was most definitely leading him on. I would allow him to drive me wherever I wanted to go, take me out to dinner, we would chill and smoke and hang out all the time. For me, he was a close friend. I was still naive back then and didn’t realize what I was doing. There was no physical attraction on my end, but I enjoyed having him around.


During Christmas break we were both back in our hometown. He would visit me at my parent’s quite often. My step-mom, coming from a traditional hispanic household, warned me about being “that kind of girl” and always being around a boy who wasn’t my boyfriend. She told me it doesn’t look right and people would judge me.


He came over on New Years eve. At midnight he asked me to be his girlfriend. I still had my step-mom’s words in the back of my mind and for whatever reason, I said yes. We shared our first awkward kiss. Theres was still no attraction on my end, but I could tell I made him the happiest guy in the world that night.


Fast forward almost three years later and we were still together. I was starting my senior year and he was entering the workforce. I was in a monotonous relationship with someone I didn’t even like, for three years because I could never break up with him. Every Time I tired, he would beg and plead and guilt me into taking him back. I always complied.


I had developed a crush on one of his friends and I knew that wasn’t right. We were all out on Halloween and his friend was there and I kept thinking how much it sucked that I was tied down. I finally realized me feeling this way wasn’t fair for either of us. The relationship needed to end immediately. As soon as we got home, I told him that was it, we were over. That was the second time I saw a boy cry over me. I could see his heart breaking with every sob and yet I didn’t shed a tear. I just sat there and watched him cry with no clue of what to say or do.


He tried to get back with me, but this time I put my foot down and insisted it was for the best. He was hurt and called me every name in the book. I let it slide and just accepted that this was his way of dealing. He cut me out of his life completely.


That was 3 years ago now and I’m happy to report he is happily engaged. I knew I wasn’t right for him and I’m so happy I followed my instincts. He has found someone who appreciates him and hopefully they have a long life together.


Federico taught me to never settle. You can’t force yourself to love someone. He taught me to not fall victim to other people’s expectations, because ultimately you’re the one who has to deal with the relationship on a day-to-day basis. Its not worth feeling trapped because you are too scared to hurt someone. Its okay to put your happiness and self-worth first when it comes to dating. Thats how you’re ultimately going to find who will truly make you happy.





I was newly 21, newly single and entering my last semester of senior year. A very interesting combination. I met Wade a couple weeks after I broke up with Federico. He was part of my school’s ROTC program. Wade was handsome, authoritative and an all around good guy. He did have a tendency to “show off” around people, but it really didn’t bother me.


Wade and I hung out for a couple of months and everything seemed to be going smoothly. We would go out with friends and it was generally a good pace for the point of my life I was in.


On Valentine’s day 2011 I drove to his dorm to pick him up since we had plans for dinner. On our way to the restaurant, some lunatic runs into the middle of the street, causing me to rear-end the car in front. Long story short, we never made it to the restaurant. When I dropped him home he gave me a kiss and told me he was happy we were ‘together’. That word activated every panic button within me and I asked him to elaborate. He told me he thought we were together when I thought we were just being casual about it. I couldn’t handle a relationship at this point in my life. He said he needed more and ended things.


I drove home in my banged up car, with a 3 foot stuffed valentine’s bear in my backseat. I ate mac and cheese and went to sleep.


Wade was in a relationship two weeks later.  This made me think he wasn’t as much into me as he was the idea of having a girlfriend. He eventually graduated from ROTC and is serving in the Army. I don’t know much about him nowadays, but I do know he got super jacked.


Wade taught me there has to be communication in a relationship. Being open with your feelings is the only way you can make sure both of you are on the same page and avoid heartbreak and awkward moments down the line.




George. The name still sends chills through my body every time I hear it. I met him at a bar through a mutual friend. He wasn’t the best looking guy but he was tall, confident and for some reason his whole demeanor just had me transfixed.


Being a petite brunette, I am the complete opposite of his type. So, the fact that he was even paying attention to me made me feel great about myself.


At this point in my life I had only been intimate with two guys, so I was pretty naive to the bar hookup culture. I also hadn’t developed my douchebag radar yet. At the bar, he would talk to me and I took that as a sign that he was interested in me.


He invited me over to his house one Sunday. I started making conversation and talking about websites. He literally took a chip full of Guacamole, stuffed it in my mouth and half jokingly told me to shut up because I was a nerd. Retrospectively, I should have taken this as a sign. Instead I slept with him that night.


After we were done, I tried hugging him and possibly going for round two. He kicked me out of his house. I was shocked. I was so used to men enjoying my company and wanting me to stay over. I felt so used and dirty. I went home that night and convinced myself that this was perfectly normal.


I saw him at the bar the next week. He told me the reason he kicked me out was because he didn’t want a girlfriend and I gave him the ‘crazy’ vibes. Yes, he called me crazy and kept laughing it off. Sadly, I was laughing along with him, but my heart was breaking. Trying to be cool, I told him I was okay with having the occasional hook up with him. I figured this was the only way to be around him, so I reasoned with myself that it was what I really wanted. I went home with him that night. This turned into a 3 or 4 month long saga.


By that time I was emotionally drained. I really liked him, but to him I was just a piece of ass. I sat him down one day and told him I couldn’t do this anymore because I had feelings for him and this was just hurting me. He offered me ‘One Last Time’ sex and my dumbass said yes (it wasn’t the last time FYI).


I can’t count the amount of people, including his roommates, who told me I needed to back off this guy. But being a stubborn girl, I didn’t listen. I didn’t care that he was just using me, that he kicked me out whenever he was done with me, that he was constantly snorting coke, I just wanted to be with him. It was hard to explain, when we were alone together things were good. We would stay up to 4 or 5 in the morning and just talk about life. He was smart and we had a lot of deep/meaningful conversations that I mistakenly took as him seeing me as more than just another hookup.  


Eventually, it ended with me seeing him with his arms around a girl at the bar. His new girlfriend.  It wasn’t that he didn’t want a girlfriend, he just didn’t want me. These were probably some of the worst months of my life. I have never felt as ugly, insecure or worthless as when George was in my life.


He moved away a year later. I bumped into him on his going away bar crawl. He tried to take me home. I said no. He now lives in California and has a beautiful new girlfriend and I’m still single. Thats how the world works.


George taught me everything I don’t want. He taught me to actually listen to people. If he says he doesn’t want a girlfriend, listen to him. Don’t go on blindly thinking there might be some sort of hope. It will most likely end in heartbreak and regret.





Finally, there’s Sam. We met a year prior to when our story begins.  We both worked for the Marketing department at the same company. I worked in FL he worked in NY. He came down for a meeting  and we sat across the table from each other, I remember thinking he was cute, but we didn’t say a word. I sent him a follow up email and asked him to transfer the company Facebook page over to me. He told me I had to add him as a friend to do it. I didn’t think much of it and figured he’d just delete me when the transfer was done. I, of course, checked his profile and quickly noticed he had a girlfriend. I left his page and forgot about it.


Turns out he never deleted me though and I would see his updates pop up on my newsfeed from time to time, including the one of his engagement.


One of his close friends works for the company as well. About a year after Sam and I had met, I heard his friend gossiping with my boss about how Sam’s engagement had been called off.


Oddly enough, about a week later Sam Facebook chats me. Its been about  9 months and we haven’t stopped talking. We clicked right away. Talking to him came so easy and I felt comfortable with him.


Before I go on, I need to say, the dynamic between him and I is probably one of the most cringeworthy relationships I’ve had if looked on from the outside.


For example, a month after we started talking he came to FL. He was planning on moving there to get away from his ex, but we both knew part of the reason he came down was so we could officially meet. Our connection was even better in person. It wasn’t all great though. This is when I first noticed how emotionally confused and broken he really was. Our connection was so organic though, that I chose to ignore it, I didn’t want to lose him. I told him it was a bad idea to move to FL. I myself was planning to move to NY. He ended up not moving.


About 3 months later, I decided to put my two-year plan into motion and actually move to NY. It was scary, but up to now has been one of the best decisions I’ve ever made.

So now we were in the same city, but our frequency of seeing each other didn’t really change much. It wasn’t about how many times I saw him. It was that it could be 2 days or 2 months and when we hung out I felt extremely comfortable just being myself.


What I thought were deep meaningful conversations at 5 in the morning with George, I now realized was a lie. With Sam, it wasn’t even about the conversation. For the first time I didn’t feel judged. It was like he’d been my friend for years. My normally insecure, neurotic self was at ease and I really felt happy with the person I was around him.


Of course the situation wasn’t always ideal for me. Sam occasionally made me upset, but it was never really his fault. He was always very open and honest with me and I was mostly upset with the fact that I finally found someone I could really like but knew it would never work out. I would also occasionally get angry, because he started this whole thing. If he had never reached out to me, I wouldn’t be in this situation.


Lately things have gotten a lot better. I finally realized with 100% certainty that things between us would never work out, while before it was always in the back of my mind. The problem is I still get that twinge feeling that I like him and its sad. I know even though I’m going out, I’m not putting my all out there because unfortunately, he’s still in my head.


Thats why today I told him I couldn’t do this anymore. I couldn’t be his emotional crutch. I couldn’t watch while he dates other women and I’m just at his beck and call. It sounds harsh, because I know deep down he’s not trying to hurt me. Hes just hurting so much more himself and theres no way I could possibly fit into his life. He was upset, but he agreed to back off.


Sam taught me the opposite of George. He taught me what to look for in a person. Even though Sam isn’t right for me, he allowed me to realize what is supposed to feel like when you’re with someone. You should feel comfortable being yourself. There should be no facades. They shouldn’t make you feel bad about yourself or like you have to hide the ‘crazy’. The person you end up with should make you feel at ease. You should be okay being alone or in a group with that person and just genuinely enjoy their company. Thanks to Sam, I don’t think I will ever settle again. The feeling I have around him is out there and I know I’ll find it again.



Every single one of these relationships has given me invaluable life experience, things you can’t get from a book. I know I will find ‘the one’, not because I stumble into him on the street or at a coffee shop, but because I’ve put in the effort into finding out what I don’t want. Achieving anything worthwhile takes work and dating is no different. So get out there, discover different people. Its worth it. When you find that person, you will appreciate them that much more, because you know all the crap you went through to get to them.


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