All the Blunders That Were My Dating Life
So, I kinda had the idea of going over my dating life, reflect on it, what I've learned, etc. This isn't a hit piece of my exes, quite the contrary, if anything its a hit piece on how bad I was at dating.
Why am I writing this? Maybe you can relate, maybe you've dated someone like me and maybe can get a new understanding from the other person's perspective. Maybe you ARE like me, in which case I hope you can learn from my fuck-ups.
The Awkward Tween Arc
I pretty much had only maybe 2 "girlfriends" in my tween years. I know it doesn't really count as dating, but maybe it's worth mentioning. Some of this might either be funny, cringey, or sad. You be the judge.
Sav was probably my first actual girlfriend. We had met because of my dad's softball team. He and Sav's mom used to date, which kinda made the whole situation kinda funny in a cosmic sorta way. Anywho, I thought Sav was cute, and so I tried talking to her. We liked a lot of the same things, and over about a few weeks of getting to know each other, we started to date. I was excited, I would brag to my friends. Then, the comments started to come. The subtle jabs at her looks were the big one and hit a part of my tweenage ego that made me decided to breakup with Sav. I didn't want to be dating an "ugly" girl. Being the spineless jackass I was, I obviously didn't say it with my chest and came up with some other excuse, something about how awkward it was that our parents dated or some shit. She understood, I think. I couldn't tell what she was feeling, we kinda stopped seeing each other as often after that. This isn't where Sav's story ends, but more about that later.
Chloe was my best friend in 6th grade. We spent a TON of time together, every recess every lunch. We would sit and talk. She was the first girl who wasn't my mother to hug me, and for a 12 year old, that shit was a big deal. Eventually we told each other our attraction for one another. I was over the moon... too much so I think. I'm pretty sure I came off too strong in that short time, as in about a week she did a 180 and told me she wasn't allowed to date. Then in about a month she had an actual boyfriend, I was crushed and we stopped hanging out. I kinda miss her, I think she would have still been a great friend, because she was. I only every saw her passingly, but we hadn't spoke since then. I wonder how she's doing. She was a really nice girl, and I hope she's doing well for herself, I think she's married last I checked.
I had the hugest crush on this girl K. We didn't date, but I think this section is worth mentioning as it was probably my biggest fuckup as a person in general. I was borderline if not all-out obsessive. I even created a fake facebook account of her and had it comment on my page saying she loved me. Fucking. Weirdo. To try and give myself some plausible deniability, I replied "okay?" to try and make it out like "hey, I don't know who this is". I made the even dumber decision to try and get her friends into buying into the fake account by having it message them trying to impersonate her. Really fucking creepy shit for a 12 year old to be doing. I think part of me knew it was wrong, but another part of me was so desperate to be liked by girls or being perceived as attractive. I got called ugly quite a bit by the popular or attractive girls my age, and that might have had an impact, maybe I was just being a demon. Anywho, I barely skipped any punishment. Got called into the vice principals office whom threatened to call the police (which even now seems a bit extreme for a bunch of kids. High school sure, but middle school? Expulsion would be reasonable, not the police). Anyway, yeah I knew how badly I had fucked up, only managing to skip out barely by using my neighborhood friend as a scapegoat, didn't know much about him so they couldn't bust him either. I don't know how I didn't get written up or suspended, but that whole interaction scared me shitless. Never did anything like that again. I've wanted to apologize to her years later for all the other stupid shit I did, but can't seem to get into contact with her. Maybe its for the best, so K if you're reading this, I am truly sorry for causing you so much choas when we were younger. It wasn't right and you didn't deserve that.
A sort of side-track in relation to my last paragraph, when my SIL was still in high school and was only dating my wife at the time, she had a guy who reminded me a lot of myself when I was in middle school. I fucking hated him, he took it WAY further than I ever did, but I saw who I could have become if I hadn't learned my lesson. He was a FULL stalker, having friends keep eyes on her after she blocked him, making fake accounts to try and bully her after she rejected him. She did pity date him for a brief period, but even my autistic ass could tell she wasn't interested at all. He would try and make out with her, but she wouldn't reciprocate. So he just sorta made out with her cheek, eventually I had enough of hearing his lips smacking on my SIL's cheek in the back of my car and shouted "hey, could you knock it off? That's really fucking gross", to which he said "I don't care". I then replied with "Well I do. So you can either sit there quietly like a good boy and quit bothering SIL, or I can drag your ass out of this car and you can walk home." He sat quiet for the rest of the trip. I was pissed, because I fully saw what I had done to K all those years back.
Back to the blunders...
Em is who I consider to be the shortest dating period ever, lasting only about 16-ish hours. I was in a friend group of about 4 other guys, and she had eyes for our buddy T. They dated a bit, but then that fell flat when he lost interest in her. I don't know if I was just the rebound, but on Halloween we dressed up as Jack and Sally by pure happenstance and this was when I started to develop feelings. I thought she was pretty, but it almost felt like fate, even our friends made the connection. So, we dated a bit. Those 16 hours, being asleep for around 8 of them. Towards the final hours, she tried really hard to convince me to break up with her, trying to gross me out by mentioning how she farts. Didn't really bother me, but she finally just told the truth that she was still into T. So, that was that. Such an odd time. My friend group kinda made fun of her behind her back, calling her names like "Cuddlefart", or when she started trying to date another member of the group C, we called her "Cock Hop". God, I fucking sucked... I don't know where she is now, but I hope she's happy.
The Early Teens
Dee was my first girlfriend in high school. She was an amateur model, so imagine my surprised when she told me she had a crush on me. Wasn't used to this. This was about when I was starting to become that post-puberty attractive. Our first date was actually at Disneyland, worked out since my family had an annual pass. This is when I think I really screwed up with coming on too strong (you might be seeing a pattern here). I did really cringey things like hug her when the ride said "hold on to loved ones", shit like that. Imagine my surprise when my goober ass got dropped a few days later.
I was hanging out with this girl G, who was a pretty good friend. We had media class together (a photoshop, video production, art class that was split into trimesters for a school year). I asked her to be my date to Winter Formal, and we had a great time. However, the blunder here came when I started telling people we were dating... we were not. Word got back to G and she told me she didn't feel comfortable around me anymore, it sucked but I understood. Seriously, why did I think that was a good idea? Was I really THAT desperate (the answer is yes). We did reconcile after my dad had passed, we didn't talk much, but we were on good terms from then on out. Sorry G, you were a great friend and I should have let it be that.
I started dating another K, for the sake of preventing confusion I'll just call her Kay to create enough distinction. I think Kay actually helped me a lot with dating, I mean who better to teach a dork like me than a girl who was into girls (more on that in a bit). I don't know if she dated me out of pity, or was trying was still in the closet (she is fully openly lesbian now). She was actually my first kiss, and even gave me pointers. It felt less like a relationship and more like sex ed really. Eventually she broke up with me, and I did the whole sad puppy dog thing. We ended up still being friends, she would even be my wing-woman sometimes... to very low success. I would say Kay helped vault me out of further cringeworthy blunder years and helped me be less socially dense. Kay actually was the reason I switched schools coming into sophomore year, that and my dad had just died and wanted a change. Thanks Kay, you helped me out a ton, hope military service treated you well.
Towards the end of my freshman year this girl who I'll call T had a huge crush on me. We had P.E. together, and her friend acted as a mediator when she found out I thought T was pretty. It went well, probably could have gone further, but again I came on too strong and that relationship fell apart after a couple weeks.
The Fuckboy Arc
Coming into my new school, I was on the wrestling team and was in my post-puberty glow-up. I was all of a sudden the "hot" guy, don't know how. Maybe all the advice from Kay actually did pay off, I definitely didn't dress nearly as dorky and stopped wearing wire-frames and started wearing Ray-Bans. I was in good shape, had abs (which was the only thing anyone cared about at the time).
El could have been a relationship. When she and I first met through our mutual friend Candy, who was my best friend at the time. She even stated to me "sorry, I'm really awkward around attractive people". My clueless ass was just like "Oh, its no problem". She later told me "yeah, dumbass, I was hitting on you". El was a great friend, and we remained good friends until she moved. I WAS attracted to her, but by the time I had announced my feelings it was too little too late. Probably for the best.
I started dating a friend of Candy's after we went to a metal band gig together as a group. This friend I'll call M. We started dating pretty shortly afterwards, Candy was pissed for reasons I didn't understand. She was "fine" we dated, but she wished we had told her sooner? I don't know. She did tell me she was VERY sexually active, to which my hormonal ass couldn't be happier with the possibility of losing my virginity. We would mostly just make out, she had a huge thing for Markiplier and Five Nights at Freddy's. She bought me a wooden Superman print for my wall (the reason was mostly because people kept telling me I looked like Clark Kent). She is also the reason I know what DDLG is... look, not to kink shame, but nah. I stuck it out because, well I still wanted to lose my virginity. That never happened. I helped her chase off some ex of hers, tried warning me that she's a cheater and a wh*re, blah blah blah. It wasn't really a fulfilling relationship, just a lot of making out and cringey X-rated roleplaying. We eventually broke up, she called me egotistical and immature, she was probably right, though when I asked for specifics she never gave me any. She did actually cheat on me, so I guess I should have listened to the ex? Maybe I would have if the guy wasn't a dick. Candy and M fell out too, Candy had this need to protect me I guess, she would always confront my ex's when the break up was bad. I saw M sometimes when Candy convinced me to go to church with her (more on THAT later).
After M, came B. B and Candy called each other sisters for a while for how much they looked alike. B was dating this other guy at the time, but I thought she was cute. Candy, B, and I went to the mall to hang out together. B and I kinda flirted, and she even showed me what a "stage kiss" was. We were alone for a bit, and she started telling me how unhappy she was in her relationship with the other guy and how she was planning on breaking up with him. Idk how it happened, but we had kissed. We actually had dated for a few months after that, even asking her to homecoming (which we never went). Now, I don't say this about many of my exes, but B was fucking nuts. For starters, she tried telling me she was a virgin because she didn't have a thigh gap and that girls broke bones after sex. Years later after our breakup, she tried telling me that she had a miscarriage and flushed the fetus in a toilet, going into detail about flushing the blood and bones. We had broken up because a friend of mine showed me a video of her and another girl making out when we were still dating, the other girl was super apologetic and said she had no idea. I dumped B because of it saying I couldn't trust her. So, there went that. Candy all of a sudden hated her, so they weren't friends anymore either.
After B came a rapid fire succession of girls who would have a crush on me, we'd date, then 2 weeks later break up. This happened like clockwork for a few months. I just loved the attention, I was always the ugly guy and now I'm the hot one all of a sudden. I probably traded in my clinginess for egotistical tendencies at this point. I dated a girl who was 2 years older than me, which for a sophomore was a HUGE deal. All came and went, I didn't care, I was just happy to have my ego inflated.
I started dating this girl Nikki, she was an ex of a friend in the clique I was part of at the time. This guy was everything I was but worse. Total fuckboy, but used drugs to hook up with girls. He'd sell them drugs in exchange for sex. Nikki wasn't into that, so they broke up. The other girls in my friend group tried to caution me that Nikki just liked to be liked, which I could relate. We dated for a bit, but there wasn't any real affection there.
She introduced me to her friend Meg. Realizing the relationship with Nikki wasn't going anywhere, I decided to start flirting with Meg. We hit it off, and started dating to which I promptly broke up with Nikki. Nikki hated Meg, but she wasn't mad at me for some reason? I'm not sure why, because she had every right to be pissed at me as much as she was with Meg. Meg was the girl I lost my virginity to. I used to walk from my high school to hers, a christian private school. We would hook up in a section of a hallway that was obstructing the camera's view. How I didn't end up on a sex offender registry at 16, I do not know. We were never caught, but the staff finally figured out I wasn't from that school, so they escorted and barred me from campus. That was the last time we saw each other in person. It was around this time that the relationship started a downward spiral. We would do snapchat sexting, but that was it.
During anti-Prom, I met this girl Ki, who flirted with me hard. Never met her before, she was introduced to me by RJ. I knew he was trying to get into her pants, but I tried to block it (without much trouble, though he did try blocking me pulling the "he has a girlfriend" card). This was technically about a month before Meagan and I broke up, and before we had sex for the first time, so I was really just trying to stick it out for that (the more I write this the more I remember what an asshole I was). Ki and I flirted, we slow danced together, I just didn't continue to pursue because I was dating Meg. Ki actually followed me on Facebook later on in life before I deleted it, she seemed to be doing well.
Meg and I broke up after a bit, Meg dumping me for reasons I can't remember, probably just the relationship was hard to keep up with really. Candy again grilled her because she knew how hurt I was. As much of a horndog as I was, I still was romantically into her outside of that.
It was after Meg that I gave up on serious dating and just tried casual hookups to moderate success.
The first serious relationship I had with this girl who I will call Monica. We had met online, and she actually was trying to get back at her boyfriend for cheating on him. When I told her I wasn't down for that, she was surprised to meet a "guy with morals". She dumped him shortly after and we started dating. I walked 10 miles round-trip to hang out with her at her house or school. We hooked up a few times, and she lost her virginity to me after a few months of dating. We broke up briefly, and I hooked up with a girl my best friend had a crush on. Despite my best friend forgiving me, even saying "ah, I knew it wasn't going to happen, it's all good man", I still feel like a giant piece of shit. After hooking up with this girl, I told her "hey, I'm sorry I can't do this, I'm betraying my best friend and that's not cool".
I got back with Monica for a brief period, but it was basically a ticking clock as I was moving away at the end of my junior year. Towards the end of my time living at my home state California, we tried long distance, but it flopped hard. I eventually learned she cheated on me after I had moved and before we broke up.
After moving out of California due to my mom and I being in damn-near crippling poverty, I spent my senior year in a new high school in a new state. Fish out of fucking water. I had brief flings that year, but not much else. I still met girls online and hooked up with them, but it never went further than that. All I really cared about at the time was getting laid to distract myself from the isolation.
Tinder Fuckboy Arc
After graduating high school and becoming 18, I signed up for Tinder, and my one-night-stands skyrocketed.
I did have 1 serious relationship with this girl during the time who I'll call A. A was a sweet girl, we went on some road trips together with her family, I got along well with her family. I still chuckle about this memory, because her dad never learned how to read, and can still hear the interaction between him and A's mom. "The sign right there says where we need to go", "How am I supposed to know what that sign says Tammy you know I don't know how to fucking read!". I tried so hard not to burst out laughing. A and her whole family were great, but we weren't very compatible. Amongst the incompatibilities, she wanted to get married ASAP and I wasn't about that, hell at the time I had no intentions of getting married EVER. The breakup was hard, I didn't want to hurt her, but I knew there wasn't really any other way. I had a conversation with her sister who basically told me "just do it, be honest, its gonna suck, but its better than lying". A is married now and seems to be happy, so I'm glad for her, she really was a sweet girl.
I continued my fuckboy arc, hooking up and then never speaking to each other.
I had a brief stint with one girl where we did amateur pornography together. After we stopped our whole Friends with Benefits situation, I tried my best to scrub the videos and photos off the Hub and reddit. It had a few thousand views collectively, so someone probably had/has it saved. Thankfully no faces were shown, so no doxxing.
I think my last serious relationship before dating the woman who would become my wife was with this girl Sam. She was really nice and funny, but probably the least intelligent person I ever dated. I probably sound like a dick for saying that, but it actually got on my nerves how she never seemed to understand anything. Her mom actually called me on her phone one time to thank me for being good to her daughter, which I thought was incredibly weird (and at the time slightly annoyed because she called me while I was trying to beat Mass Effect 2, stupid I know that THAT was my priority). I had a lot of aspirations at this point, big dreams of grandeur. This was the reason she said she broke up with me. She felt like she was getting in the way of my dreams, that and she was mad at herself because she was really insecure at the fact she couldn't ever reach orgasm.
Now
I met the girl who would become my wife when I had just put in my two-week notice at this place I was working at and she had just started. She was actually dating someone at the time, this total asshole. The whole relationship was toxic. I had some clue that it wasn't going to last because of how she talked about him. Now, normally I would stop pursuing someone when they state they were taken, but something in my gut told me to just hang on a bit.
We became friends at work, she later told me she would cancel plans with her BF to spend lunch with me. We eventually hung out outside of work, what she and I call our "date-not-date". The flirting was on full blast, I even threw her over my shoulder as some kind of "macho" thing to try and make her feel more attracted to me, surprisingly it actually worked. We eventually hung out in her car, and she came clean that she wanted to break up with her BF, she just felt bad for him, even after he threatened to hit her. Emotions were high, and after all the flirting prior, I said "fuck it" and kissed her. I've never felt fireworks before, but that first kiss was actual fireworks. She did break up with her BF that day. Were we immature in this? Yes, but what do you expect from a 17 and 19 year old.
I renounced my fuckboy tendencies, and fought hard against my attempts at self-sabotage. We survived COVID together, long distance, death of loved ones, and so many other challenges. And I couldn't feel more lucky. I feel like I had finally won. I have a comfortable life with an amazing woman who is just as crazy about me as I am her. We are razing a beautiful baby girl and 3 cats together. It gives me a reason to get up every morning.
Conclusion
I've learned a lot over my years, and I can proudly say I am nothing like how I was 5 years ago, let alone 7+. To anyone I've hurt, I truly am sorry. I know it might not mean much since it's unlikely this will ever reach you, but I am. I regret how I might have handled certain situations, some of you were right I was immature or egotistical. Some of you still saw that I could do better, and I thank you for having that faith in me.
In the end, I wanted to write this as a reflection of where I went wrong and how I've grown as a person and to maybe teach anyone who might stumble upon this what NOT to do. If we dated at any point I wanted to thank you and also again apologize. I know I could have probably been a better partner, but you are the reason I am a better person for my wife. Its because of you I'm in a happy and secure marriage, and can be a better example for my daughter. They say girls date boys who are a reflection of their father, so it is my mission to ensure I am my best self so my daughter will find a good man.
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