Everything I’ve learnt from dating in my early twenties

A love letter to a past me, and maybe to a present you.

In the name of peak vulnerability, I’m here to lay bare the lessons I learnt from dating in my early 20s. Failing, falling in infatuation (not love), and finding silver linings are some strong themes ahead.

This is a condensed version of all the lessons I wish I could have pre-learned (but that defeats the entire purpose) from age 20 until now. I am currently 24, for context, and I’m in a healthy relationship, for real. 

Interested to hear how others navigate the world? Head to our Life section.

For all the naivety, romanticism, tequila shots and tears I threw at pseudo-dating, I applaud myself. The reason I say pseudo is because all of these findings were accumulated before actually entering a long-term relationship. Please do keep in mind that what follows are some extremely subjective field notes, and they will certainly not apply to every love-seeker reading this piece.

Listen to your friends (to an extent), as they know you best

If only I had a dollar for every time one of my best friends was right about someone before I knew it. Trust your intuition, but pay close attention to the gut instincts of your greatest confidantes. In saying that, you also must measure what grievances you express to your inner circle if you’re not ready to face some harsh realities. 

For example, if you’re dating a terrible person and your friends can see through the relationship façade, you’ll need to remember that they want what’s best for you. They’ll tell you when you’re not being treated the way you deserve to be. 

Be fair, be honest, and lean on friends for support when you’re struggling to figure things out. If they’re really good ones, they’ll give you a few chances (and breakdowns) to figure shit out and eventually you’ll dump the loser (or they’ll just never commit to you). And if you’re keeping things from your friends at risk of them vetoing the love interest, that person is probably a royal dud anyway. 

When you’ve struck gold, it can be incredibly exciting to introduce your friends to the Real Deal. While it might take your friends some time to embrace a new human, remember, that’s literally how it is with any relationship in life, platonic or otherwise. You might be smitten, infatuated, or even deeply invested in your new person, but it’s important to allow your friends some time to get to know them and integrate them gradually into your life.

More often than not, your favourite people have been around for a lot longer than the potential paramour, so it’s vital to honour that and understand beauty is in the eye of the beholder. Chances are, when the right person comes along, they will suddenly click into place (after time) with all the other important people in your orbit. You’ll forget what life was like before them, but simultaneously remember you owe a lot to the people who picked you up each time your heart was in jeopardy. 

Please, make mistakes

In Suddenly 30 (the cult early ’00s film about being careful what you wish for), the future version of Jenna, the film’s protagonist, asks her mother if she’d made any mistakes in her life. To that, she responds, “I know I made a lot of mistakes and I don’t regret making any of them”. Jenna replies, “How come?”, to which her mum says, “Because if I hadn’t made them, I wouldn’t have learned how to make things right”. 

I think about this quote often, because it really captures the value of fucking things up occasionally when you’re learning to love in quasi-adulthood. You’re the sum of the formative experiences and lessons you’ve learned so far. And my god, that really pertains to dating.

Without the unfortunate endings and mishaps and failed situationships and cry-selfie flashbacks from two years ago on your Snapchat memories, you won’t know the difference between shade and light. Without collecting a litany of red flags, you may not ever be able to distinguish them from the green ones. Without shitty first dates, you couldn’t appreciate the beauty of a brilliant one. 

Don’t wait around for someone to love you

Lizzo’s recent hit ‘2 Be Loved (Am I Ready)’ is actually a lyrical work of art masquerading as a carefree bop. The sentiment that flows through her lyrics is one I can relate to deeply. She says, “You found me, I was fed up with the fantasy” and admits that “yesterday, I would have run away”, but now, “I don’t know why, but I’m ready”. She’s ready to be loved! The song is sung as if it were a conversation between her and one of her best friends. Lizzo questions her friend: “That’s why I’m asking you, ’cause you know I’ve been through”. 

I think one of the most confronting things I’ve realised is that some of us chase people we subconsciously know are completely unavailable. Maybe we hold false hope, but deep down, we know there isn’t a realistic future with that person. Perhaps it’s to reinforce bygone pains, or maybe it’s a covert fear of being loved.

After all, when everything is going right, it leaves room for things to go wrong. That is a terrible mantra to have and it’s one I’ve rewritten. Let love in (when it’s right), let things be good, let go of mistrust and let yourself be happy. When you’re ‘in it’ with someone, ask yourself: “Am I being treated the way I truly deserve?”.

Never compare scripts because every single relationship is different

It’s not about what it looks like from the outside, it’s about how it makes you feel. Whether you’ve just started dating someone or you’re nearly a year in, one of the most valuable things to remember is that the most important perceptions of your relationship are the ones that come from the two people in it. Nobody else. (This is obviously different to my friendship paragraph above: please listen to them). I’m talking about comparison here. 

People might swoon over date nights on Instagram or weekend getaways or anniversary celebrations or later, wedding grandeur. But in the context of love, comparing is illegal. You have no idea what goes on with two lovers behind closed doors, or how drastically different the projection of a relationship (online or otherwise) can be to its reality. 

The only thing you must concern yourself with is how your love interest makes you feel when it’s just the two of you. Are you happy, truly? Do you yearn to see them again after only 24 hours apart? Is it worth sacrificing, compromising and meeting in the middle? Do they add immense and irreplaceable value to your life, and you theirs? 

Every single person has a different dating context and history to the next, and the way we act in new relationships is heavily influenced by past ones. Your unique relationship will differ in so many ways from that of your best friend or your parents or that fashion designer you follow on TikTok. 

Be resilient

My biggest takeaway from the dating circuit is that love is a game of numbers, chance and coincidence. You are no more loveable or attractive or special than the next person because you have a romantic partner and they do not. It all comes down to one big fat stack of cards that the universe is holding. 

But resilience is what matters most. And practice. In order to date consistently and meet new people, you’ll likely need to repeat the same small talk, background stories and getting-to-know-you activities a number of times. But all of it is character-building, plot-enriching and confidence-building (even if it doesn’t seem like it at the time). 

Maybe you’ve cut dates short because you’re still into someone terrible, and you’ve ignored some good fish in the sea because of clown girl behaviour. The alternate endings existing in parallel galaxies could be far different to the one you’re living in now, and that’s fine. You’ve probably had some good-ish first encounters and some unhappy endings, but that’s all part of it. And trust me, weeding out what you don’t want will be the best training you need to distinguish someone that is right, or at least a vast improvement from your last endeavour.

Also, resilience should teach you how to reframe your approach to dating. Like learning that you can never judge a book by its cover or a dating app profile by its byline. Humans are very intricately layered onions in need of a lot of peeling to get to the juicy bits. Stop making repeated errors or following the same habits. For me, this was ensuring I never pursued a manchild with filthy bed linen and a God complex again. 

Love is not a cure-all or a magic solution to your problems

The idyllic person we imagine will come along and make everything rosy and perfect does not exist, and love is not instantaneous. The right person doesn’t necessarily have particular physical traits or qualities you have on a mental checklist. They are also a unique individual with their own set of ‘things’ going on – insecurities, strengths, past relationships, flaws and so forth.

But what this friend/companion/partner will do is challenge you to push yourself to achieve what your highest self is capable of in every facet of life, and you’ll do the same for them. They will see you ‘warts and all’ (as my mother likes to say) – when you’re sick and sad and disappointed. They’ll also be there to cook for you, calm you, slow dance with you in the kitchen without music, hold you, buoy you, humour you, ground you, surprise you, and unlock feelings in you that are entirely new. 

Love is not a cure or a Promised Land, or a lifeboat, but it is the force that will change you in ways more complex than you could have ever imagined. The best part of love is the quiet moments between the two of you that nobody else will ever know about. And it’s how they remind you of the other greatest people in your life, past and present. 

My love reminds me of my pop; the gentle but strong, deeply loyal and hardworking man who helped raise me. He also reminds me of the friends and family I love now. He reminds me of the love I have for myself, too, because I can see the qualities he cherishes in me. And maybe those are the qualities I forgot about along the way. My love’s name is Ben, and I am very glad to have found him. He’s made it all worth it.