Someone DMed me this ^ yesterday after sharing my post around turning thirty. And it sent me into a spin. I know I’ve shared a lot over the years about dating (and sometimes, choosing not to date), so it’s normal for people to think that’s largely all I’m obsessed with. Or care about. Or lose sleep over. Don’t get me wrong – I do love to talk and think and write about good dates, bad dates, the ideal first date, the ideal last first date…
…but does that mean I’m perceived as a bit tragic? Desperate? Undateable? Probably. (And no, this isn’t new to me – I’ve had a fair few people ask, or tell me, if sharing ‘all of this’ on the internet with everyone and anyone is the best idea.)
So, if you’re wondering why I’m ‘obsessed’, here’s my answer.
I always felt like I was the ‘ugly’ one
Woe is me. Cry me a river. Boo bloody hoo. But it’s true – I never felt pretty in school (I’m certainly not the only one) and I did my best to make peace with it veeeeery early on. Getting called a ‘boff’ day in, day out doesn’t tend to go hand-in-hand with being drop-dead gorgeous, eh? Instead, I leant in to what I was good at – behaving, revising, and making and keeping a lot of lovely friends.
I didn’t join in with the spider lashes trend, where the ‘it’ girls would layer and layer mascara onto their eyelashes until they resembled the thick legs of a beasty spider – partly, because my Mum wouldn’t have allowed it, and secondly, it looked shit, let’s be honest.
I never dyed my hair the reddy-purple that was all the rage in the late 2000s, early 2010s or styled it with a swoopy fringe hairsprayed to within an inch of its life across most of my forehead. (Thank goodness.)
And I didn’t wear the trendiest or hippest clothes (the fact I’ve used the word ‘hip’ there tells you everything you need to know). It would’ve been nice to have dressed like the ‘cool’ girls and get to carry around *the* Jane Norman bag to show that I’d shopped there (I mean, what was all that about, hahaha). But then again, would it? Would I have felt less ugly, more pretty if I was dressed the same as everyone else? Would it have really changed that much?
What’s cooking, average looking?
You get the idea. When you’ve made peace with the fact that you’re not one of the pretty girls, or ‘fit’ girls as they’d become in their teens, you start to find other ways to fill your cup. Sure, after school history lessons on a Monday night weren’t the epitome of being the ‘cool’ girl that all the boys fancied at 15, but hey – I got the English Baccalaureate, so who’s really laughing? (Everyone else, actually, because the ebacc wasn’t as special as it was hyped up to be. Lol.)
These feelings of being sort of ‘average looking’ carried on into adulthood, from the year in Paris looking after five kids surrounded by the slimmest, chicest French women, to the first, second, and third ski seasons where everyone, and I mean EVERYONE, was properly ‘cool’.


Then we moved onto the weird year I spent working at an estate agent’s, where I wore heels and a pencil dress every single day to try and fit in with *the* aesthetic (I KNOW), to the three months I lived in Tanzania, no heels or makeup in sight. (OK, apart from my eyebrow shade. Every girl has a vice.) I remember feeling so self-conscious on the first few nights of that trip, like, to a horrible level, when I met the rest of the people I’d be spending the next 12 weeks with. I mean, I was 22 or 23, had finally broken up with the guy who didn’t exactly make me feel great about my appearance, and there I was without a scrap of mascara, wearing zip-off trousers, ginormous and clunky walking boots, and a £5 t-shirt from M&S that said ‘Love Life’ on it…
…what doesn’t kill you makes you stronger and all that.



The changing face of my relationship with my… face
ANYWAY. In my mid-twenties, my feelings towards my own appearance started to change. I didn’t think I was a model by any stretch of the imagination, but I started to find my feet with what I bought for my wardrobe. How I did my makeup. What hairstyles felt like ‘me’ (note the bob I got cut a few Christmases ago). And with all of this came a confidence that I’d not really had before – a confidence that was then charged by the dates I started going on and the types of guys who started taking notice.
How cliché.
I won’t pretend I didn’t enjoy it – or that I don’t still enjoy it (when it happens, hahaha) – but it also quickly turned into a bit of a vicious cycle, this need for men to validate that I’m pretty or fit or even sexy, rather than anyone else, particularly not me.
The OG reason I thought I was obsessed with dating
Dun dun duuuuuuun. Feels like it’s starting to get a bit heavy, eh? Don’t worry, I’ve done a lot of therapy to understand and sort all of that out.
(OK, most of that.)
Anyway, when I started writing this, I didn’t think we’d have gone down this rabbit hole. Instead, I thought I’d be telling you that I write about dating because I’m FASCINATED by relationships, because I have a loooot of love to share, because my parents divorced when I was 18, which rocked everything I thought I knew about marriage.
All of the above is absolutely true. But in its simplest terms, I think I’m ‘obsessed’ with relationships because I’ve never really had a proper adult one. (Least not one I’d count as ‘proper’.)
When you’re a kid, finding a boyfriend, getting engaged, walking down the aisle, and having children of your own are made out to be so easy. Like, SO easy. And the truth, one of the 5,614 hard truths you learn as an adult, is that it’s not easy, at all.
It’s actually really hard.
I can joke about being perpetually single, but it’s true – everyone I’m surrounded with has had at least one, two, three ‘serious’ relationships in their twenties, and I’m over here wondering how I missed the boat. Like, how do people find their people? How do you break off one relationship and then get into another, pretty much straight away? What do you have that I don’t? How do you know that you want to be with them forever? Like, what is that feeling? That moment? How does it happen?
The guy(s) I thought I’d marry
Hand on heart, like properly on heart, I’ve never really fully felt like I’d spend my life with any of the guys I’ve dated. Sure, I’ve been like 98.7% sure, but never the full hundred. (Hearts are shattering everywhere – sorry dudes.) There’s always been something, subtle or obvious, that wasn’t right.
I’ve never not felt on edge, always a voice in my head reminding me that this person could change their mind and leave. I’ve often felt like I’m a bit of a joke, that guys see me as a good time but not a long time. And I think I’ve always tried really hard, too hard.
While all this says a lot about me (you can anxious-attachment diagnose me all you want), it also says a lot about them and how they’ve made me feel (or not feel). And you know what? I always ends up back at the idea that they can blame timing or something feeling a little ‘off’ or their avoidant attachment style, but deep down, there’s always part of my that believes it’s because I’m not pretty enough.
Get over yourself, you shallow girl!!! Right?
Plot twist
I hate to admit it, but hey, we’re all human. And as girls and women particularly, it’s what a lot of our worth still feels like it’s pinned on, especially around dating, whether you like it or not.
None of this, however, is to say that I haven’t wanted to be with one of or any of these guys forever. In fact, I’d say the opposite is true, and I’ve spent houuuuurs convincing myself that yes, Gabrielle, you could, in fact, be happy waking up next to the guy with scarily long fingernails for the rest of your life. (As long as you bought them a pair of nail scissors for Secret Santa.) Or, the guy who told you after three months that he wasn’t so sure they wanted something serious, but in the same breath went on to tell you that the next relationship he was going to have was going to be end game, the one that’d end in marriage, and he thought that person was you. Or, the guy who you went on a date with just the other week who everyone said sounded sooooo nice, but there was just…
…something.
Ah.
The real reason I love, loathe, love it
All of this to say that dating has become something of a curiosity to me. Meeting someone you don’t know for the first time, who could be the last first time you meet someone, is, quite simply, a thrill. Particularly when you’re an all-in romantic.
Nine times out of ten, I’ll be sitting on the bus or in an Uber en route to a bar with the absolute highest expectations of what it could be, how that evening could change my life forever. (Don’t worry, I’m under no illusion this is the healthiest or best way to approach a date – the opposite, in fact – but hey, you’ve got to be in it to win it.)
And if I am in, I’m not starving myself of the ‘what if?’ butterflies. Because there’ll come a day when it’ll be the last time I have them, and I only want that to be when I’m with the person who I really see as being forever. Short fingernails and clear intentions about commitment and all.
So, is that why I’m ‘obsessed’?
How far I’ve answered the question, I’m not sure. This whole piece feels messy and all over the shop and like we’re only scratching the surface, but then I guess that’s dating and relationships and marriage for you.
But I will say this: All of this dating malarkey is just a small part of my life, which is otherwise full of the best friendships, parents who drink pints, evenings pretending I know how to play tennis, long calls with my brother, weekends teaching myself to sand, paint, and wax cupboards and walls and doors in my flat, Aperols in the sun on the slopes, silly made-up games with my nieces, lunch breaks in the library, letters from friends and penning them back, solo holidays because I can, using coconut cream to make a katsu sauce rather than coconut milk and having a strop when it doesn’t work, running to the Legally Blonde soundtrack, Ben & Jerry’s sundaes during 241 cinema trips with the girls, and this Bank Holiday Monday trying to shift a cold but relieved for the downtime and a moment to write.
(Oh, and time to reply to some messages on Hinge.)
😉
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