Things I learned from dating in my 20s

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I grew up in a religious Christian household, and the friends I had in my early adult years had a large impact on how I saw relationships and dating in general. The clichè “finding a Godly husband” when you’re young is exactly what I was fed and being a big, fat, romantic optimist at heart, I lapped it all up! Safe to say I fell in love with my youth pastor at the age of 17, and was heartbroken when he - 14 years my senior - moved to Dubai overnight to marry the woman “God confirmed to be his wife” during my senior year of High School. Looking back it all worked out for the better, as I was so young and impressionable at that age, I literally would’ve taken my life in any direction and tried to make it work with this man. Only to wake up one day in my mid-thirties and realise that the life I built so meticulously, whilst losing every little bit of myself, wasn’t at all what I wanted. 

Is it better than my current reality - recently single at the age of 32? You freaking bet! I’m still an optimist and a big, fat romantic at heart, I’ve just since become a lot less forgiving and much more skeptical. What follows is a summarised version of my dating history over the past 15 years, and what I’ve learnt. Maybe you have similar stories to share, maybe you think I’m lucky, maybe you pity me - that’s all perfectly okay, as I am happy with where I am today and I know, having experienced the kinds of love I have so far, that the best is certainly yet to come.

Fearless and fun

I had my first kiss at the age of 12 with the neighbour’s kid across the road, but then I also broke up with him 4 days later during the summer holiday as I “didn’t want to be tied down” - maybe tween me was onto something? Unbeknownst to me, I wouldn’t have another kiss until the day of my 18th birthday, and I also don’t recall being in many relationships during the age of 18 to 21, as I knew that the men that showed interest in me, weren’t necessarily the ones that God would choose for me as a husband - subsequently excluding myself from the dating pool due to my own self-righteousness. I had a few flings during Varsity, and dated this one guy I met at a wedding for a few months. He was a Christian farmer with a Law degree, he played rugby, had a killer jawline and had kind, blue eyes. But as time went on, I realised our futures weren’t going in the same direction at all and I’d rather throw up in my shoe and wear it for a day, than move to a farm out in the middle of nowhere. Nevertheless, I ended things after 8 months. The last straw was getting pictures of his dirty overalls with the caption “you’ll get to wash those one day” - it’s also the day I became a feminist. I graduated the next year, and had some more casual flings in the mix. 

I was lucky to start my first real job a few days after my final exams and I don’t know why, but I saw this guy there, man rather, as I was 23 at this stage, and he was 9 years my senior. Enter another cliché - falling for the bad boy because you think you can change him. 

Lesson 1: Don’t ever date someone with the intention of changing them, even if it’s something miniscule. You’re setting yourself up for immediate failure and disappointment. 

We shared some drinks during social hours and I could definitely tell he was flirting, only I was too stupid and naive to realise that he was a massive player and would go wherever he got attention and validation. Maybe this is why Leo DiCaprio dates young girls, because they’re inspired by him, and offer constant validation and admiration, feeding his very large and aging ego? I digress. Let’s call this man “Ben”. Ben and I hooked up a few times over the span of 4 years, whilst I dated other people and he subsequently slept with multiple of my respected colleagues. It doesn’t matter who I was dating during this time,  how extraordinary they were, or how many ticks they had on my list of criteria, I just couldn’t fully commit. Looking back now, I know this was because Mr. Ben would never fully commit to me, so I would always walk around with giant “what-ifs” and take them into every relationship I tried to build, which is not only unfair to the other person, but also very unfair to me.

Lesson 2: Never enter into a relationship in an attempt to get over someone else - you’ll only end up hurting more. 

I never got closure from this screwed up relationship, even though we’d speak every day, go on dates and see each other over weekends. I eventually realised that Ben was only stealing my peace, through his piecemeal offerings of contact and friendship. That man tried every trick in the book to stay in contact with me, even asking for my mechanic Dad’s details so he could have his car serviced - might I add, a car he didn’t have at the time. I took active steps to avoid him, and limited our personal and professional communication as much as possible. Until one fine Tuesday where he would walk up to my desk and tell me we had to speak. After finding a private place to talk, which = another red flag: He never wanted anyone to know about us, for fear of what it would do to my career - bullshit! 

Lesson 3: A red flag, is a red flag, is a red flag. And if he wanted to, he would have. Never date someone for their “future potential” - you have to put up with who they are now, and if you don’t like who they are now, then why subject yourself to that? 

Let’s try again. After finding a private place to speak, he would begin to tell me how he couldn’t see his life without me, that he was 100% ready to commit to me, that everything reminded him of me, and that he was in love with me. So that’s the outcome I wanted, but finally hearing him  say those words out loud, made me realise that I didn’t want to be with him. Having to keep everything a secret wasn’t how I wanted to live my life. I knew I wanted someone who was proud of me, who wanted to show me off, who didn’t sneak around and cheat on me every chance he got. I wanted someone who was driven, who treated women in general with more respect. Someone honest, who didn’t lie when things got tough. 

Love-bombing is real and we need to be vigilant

Shortly after my chat with Ben, I met “Matt” through mutual friends. Matt was a recent divorcee; deliciously tall, dark and handsome; had great hair and a chiseled jawline (obviously I have a thing for men with strong jawlines!). Some red flags right off the bat include Matt not owning a car, or having a job, or owning any clothes beyond two t-shirts and a pair of swimming trunks - but come on, that chiseled jawline though, who can blame a girl! On our second date he told me he’d been diagnosed with leukemia with only months to live and that God had shown him he needs to pursue me. He also made his intentions very clear from the start - he was looking for a relationship, he liked me and he was ready to commit. These were all the things Ben never said to me until the very end, so naturally I thought the Universe was finally letting me have a turn at love, causing me to cast a blind eye to the multiple red flags. Matt would show up to every date barefoot, high as a kite from the “marijuana his doctor prescribed” and wait on me to pay once the bill arrived. Yet, he would send me voice notes with very off-key love songs he’d written for me, pick me flowers from someone’s garden and cook dinner for me - so I thought the gestures and effort were worth so much more than the traditional gender roles we were expected to fulfill. We had a whirlwind 5-month romance, after which Matt would invite me out for a beer to the bar where we had our first date and proceed to break up with me because I was “too driven and mean” - did I mention I was also studying for another degree during this time and had a full-time job, so I could only see him twice a week? 

Lesson 4: Sometimes it really isn’t you, and the other person needs to sort out their stuff. You gave it your all. It’s not your fault it didn’t work out.

Two weeks after Matt and I broke up, my sister sent me screenshots of a recent Facebook post where he had been tagged on a birthday weekend away with his new girlfriend - a mutual friend of ours. He was also declared to be miraculously healed of leukemia. Of course I was absolutely heartbroken, and even thought about messaging Ben at my lowest. Luckily I had a really great group of girlfriends at the time, who stuck by me and got me through it.

I tried every dating app so you don’t have to

A few months following my split from Matt, I decided to finally download Tinder and create a profile. I went on a few dates with some guys, but nothing stuck. Some matches went past the 3rd date, and then died out due to either realising our incompatibility, or just due to the sheer volume of choices available on the app. It’s so easy to imagine what life could be like with someone based on a few pictures and mediocre interactions. I’ve since gotten my fair share of dick pics, which my friends and I refer to as “Richards” as that seems less harsh, and somehow more socially acceptable. As soon as I saw one too many of my colleagues from work on Tinder, and noticed that the app is optimised for hookups, with its major purpose of having users download and redownload the app, I turned to Bumble and yet again created a new profile.  Bumble was a bit of a more civilised place, as only women can send the first message once there’s a match. Yet, after a few months, the same men would reappear, some of whom I remembered from Tinder. So my pool was getting smaller, and so was the potential for a meaningful match. Cue “Koer” - An Afrikaans celebrity in South Africa then proceeded to launch a dating app for the Afrikaans community, Koer - so I downloaded it and yes you guessed it, I created yet another profile. Koer was by far my least favourite, as not only did I have to speak my mother tongue against my will, I also had to stare at pictures of men in two-tone khaki outfits and vellies, knowing they’ll respect their Mothers, but expect a woman to do everything for them. After matching with one too many men in said two-tone khaki outfits, I promptly deleted my profile and the app from my phone.

When 2020 came around, I was still desperately single (a few months post-Matt) despite all my efforts and profiles and I was ready for a new something. So naturally I had concurrent active profiles on Bumble, Tinder, and a new variable in the mix - Hinge. Hinge’s tagline is “designed to be deleted”, and the app is great at getting people to start a conversation, something that Tinder greatly lacks, so I had hope. I went on a few good dates, and then some terrible ones! I had a video call with a guy in hard lockdown, where he proceeded to jerk off and tell me to sit still (I was fully clothed in winter wardrobe) until I eventually realised what was going on, and made an abrupt exit. I went on another date with a guy who had custody of his ex’s cats, and after telling him that I’m allergic to cats and I don’t think this would work, he proceeded to put the cats up for adoption - luckily he found someone special recently, not-allergic to cats, so that one turned out well in the end. One of my final and most recent dates was with a guy I had as a connection on LinkedIn - I admired him professionally, and was all too flattered when we matched on Hinge. I wasn’t even home yet after our first meet up - a casual coffee in Sea Point - when he said he had a spare bedroom, and asked if I wanted to move in - safe to say that ended really soon too. 

Lesson 5: Sometimes dating is just meeting really interesting people, and realising that it’s not for you. Many people have found love on dating apps, but we’re all different, so not being able to find lasting, meaningful love on a dating app doesn’t make you inadequate in any way. 

Frivolous and flirtatious

I decided to start my MBA in the middle of 2020, which along with a full time job in the EdTech industry, meant I had very little time for any relationship matters. My weekends were planned far in advance, and I focused heavily on my mental health during this time. I noticed I would leave certain friends and feel completely drained, and others would leave me invigorated and feeling inspired. It was during this time, that I became way more protective of my energy, and more cognisant of which social interactions I was willing to give the little free time I had. Safe to say some friendships ended, and others got nurtured a lot more. I graduated with my MBA at the beginning of 2022, and met this guy on Hinge - let’s call him “Magnus”. Magnus was a tall, blonde Norwegian viking with a chiseled jaw, recently single from a 3 year engagement, and currently working as a nature conservationist. Magnus was fun, unassuming, and non-serious. We didn’t last long, but he / it was exactly what I needed after the academic rigour I endured for almost 2 full years. 

Lesson 6: Sometimes it’s okay to have fun, let go, lean in, and discover ways you never thought you would see yourself. Fall in love with life and the impossible, and not expect any long term commitment. Just be smart and guard your heart, and trust a man when he says he doesn’t want commitment - he’s not going to change his mind about it, it doesn’t matter how special you are.

I met my most recent love at a friend’s wedding a few months ago. “Jeffrey” had apparently known about me a few months prior after seeing a picture on a mutual friend’s phone. Knowing he had to meet me, he asked to be invited to their wedding (kind of romantic right?). Jeffrey showed up with the most infectious energy. He had the kindest, most gorgeous blue eyes, and a wide, white smile that would make the skin next to his eyes crinkle. He was also super tall and demanded attention wherever he went. Not only did he turn out to be the most selfless individual, he was also respectful, could dance really well, and was great at conversation. A dear friend of mine eventually coaxed us into sharing numbers and meeting up after the wedding, as we lived 1000km apart - literally, in completely different provinces of our country. Following the wedding, we spoke all day, every day. Less than two weeks later, he asked if he could come visit me for 10 days, to which I agreed and started the countdown. He did and said everything right, even though in my gut I felt we were too different, I was constantly reassured that “opposites attract” and our differences are what will keep things interesting in the long term. 

Lesson 7: Listen to your gut - if something feels off, it is. You know yourself the best, so be careful who you run to for advice on matters of the heart. Not everyone has the context you have.

Red flag #1. Jeffrey turned out to be a bit of a racist, blaming his background and where he grew up. I thought I could try and get him to open his eyes, but he stuck to his opinions as hard as I stuck to my non-racist ones. Red flag #2. Jeffrey was also a Trump supporter - even though Trump has been found guilty of sexually assaulting dozens of women throughout his life. As a feminist, this always remained at the back of my mind. Red flag #3. The fact that I was earning 3x more than him, and he never showed any outward qualms with it. Yet his behaviour started changing a few months on, and I found him to be more belittling towards me, and less supportive and interested in my job. In the end it’s not my responsibility to make him feel like a man, and I won’t apologise for where I’m at in my career, because it took more than just a bit of hard work and sacrifice. Finally, Red flag #4, I explicitly told him I don’t want kids, but that I’d be open towards adoption. I didn’t want my body clock to hold me back from achieving the goals I’ve set for myself, so I removed the pressure and potential disappointment altogether when I turned 28. Once again he seemed fine with it at first, but as we continued dating, the topic would come up frequently and he’d always enquire as to whether I’d “changed my mind now that I’ve met him”. Which just tells me that he’s a tad narcissistic. Our relationship eventually ended, and I’m okay with that.  I experienced many firsts with Jeffrey in a short span of time, and I wouldn’t trade them for anything. I’m grateful for the lessons I learnt, as I now know what I’m willing to compromise on, and the things that I definitely won’t be able to look past.

Lesson 8: Be clear on your non-negotiables, versus what you’re willing to settle for. Those issues won’t go away, instead they’ll just be magnified as time goes on.

Forgiving and future-oriented

Obviously this article isn’t about a Cinderella who found her Prince Charming. Instead it’s about a 32 year old driven, ambitious, successful, educated woman’s dating journey through a little more than a decade, and what she’s learnt. Yes, I don’t have someone life sized to cuddle with, but I do have a tiny dog and very fluffy cat to keep me company (note I take daily antihistamines for said cat). I also recently started a business and bought a home, all on my own, and I genuinely love my life. I love my job, I love the people I choose to surround myself with, I love my pets (read children), and I love knowing that when the time is right, the right person will eventually come along. For now I’ll continue being the best person I can be, and continue improving and developing myself, for no one else but me. I’ll continue to go on solo holidays and meet the most wonderful people who’ve since become friends, drink all the good wine, and eat all the good food. And I’ll continue living in peace, knowing I don’t have to apologise for who I am, or how much I spent on a recent shopping trip. Best of all, I can pee knowing I’ll always find the seat in a downward position.