What I learnt by dating ‘up’: and why I won’t ever, ever do it again

It’s good to respect your partner. But don’t date someone who won’t respect you

I’ve just turned 28 and I’m still learning life lessons, even today, even this week, even this month. Before, I’d have been really embarrassed to talk about what I had got wrong, what I had failed at, and what my insecurities were, but now I am coming to understand that anyone who doesn’t believe all humans are flawed, riddled with disappointments, and inclined to do stupid and ridiculous things, is very, very naïve. And I’m still naïve: but I am learning.

Not doing this, again

I, ladies and gentlemen, am not a duchess, or a princess. I’m not a top CEO, I have never won an Oscar, and I’m about as likely to win the Olympics as ‘Crack’ Barry from Swindon. I’m not especially beautiful and I’m not especially intelligent. I’m just Madelaine, or Maddie, depending on how well you know me. I’m frivolous, I’m a daydreamer, I’m sensitive, I like drawing and writing stories, and I’m never happier than when I have a cat on my lap or a warm fire. I fall over in heels. I’m easily pleased. I feel uncomfortable with ‘staff’. I’m a simple creature and I’m at peace with that. I don’t hate that my eyes are swamp brown and I don’t mind that my dresses aren’t from Prada. I don’t think I’m perfect: but I do think I am enough.

For the right person.

I’ve historically dated ‘up’. I’d excuse it to myself as wanting someone who was intelligent, interesting, and someone I could learn from and respect. Which is fine but there we go: that was a choice I consciously made. My boyfriends were ultra-high achievers: top economists and doctors. The men I dated were CEOs, creators, and founders. I liked the way they spoke, I liked the light in their eyes when they talked about the world. I was fascinated by the stories they told and the things they had done. I learnt so much, constantly, consumed with a wide-eyed dopamine hit of someone I admired. It wasn’t a money thing, before you say that: I’ve always had my own money, my own career, and paid my way. I’m not a parasite or a gold digger and I wasn’t brought up like that. I come from privilege and I’m very grateful for never having been a moth burnt by the light of a better world with the wrong man.

I kept encountering the exact same problem, ad nauseam: they’d be totally infatuated with me, and then gradually realise I didn’t fully understand what an ASR or notional compact renewal was, I wasn’t a glittering enigma of unattainable erotic glamour, and I most certainly wasn’t on their level. And that would absolutely crush me, over and over. It really hurt. I’d lie there sobbing in the shower, pressing my palms to my eyes like a child and begging myself to just be a little bit more informed, a little bit less immature, and a little bit better. The sense of failure just consumed me every time I heard that note of contempt spit from their tongues. I disappointed them constantly by not being the woman they imagined. My ‘unrelenting kindness’ became weakness. My ‘joy at the world’ became my ignorance. My ‘extraordinary insights’ became vapid and uninformed. My ‘fascinating excitement’ became frivolous and my stories became self absorbed. I stopped being gentle and vulnerable and started being insecure and annoying, to them. Everything I was just frustrated and irritated them. No matter how kind, present, and loving I tried to be, I was never, ever enough. No matter how hard I worked, no matter how much I tried to fix what they didn’t like, I was always pathetic and annoying by the final curtain. I was the nice country girl to fuck and use up before they married the 34 year old hedge fund princess in crisp business suits from Virginia Water.

And it destroyed me.

I don’t do casual: I never have. You’re my partner, potentially my partner, or you’re a strictly platonic friend. No other options, and you don’t move in or out of those boxes. So this rejection stung deeply. My chest physically hurt, my throat tightened. I wondered, again and again, if I was just essentially unlovable. If there was ever going to be a point I could be me- really authentically me — and not be rejected and looked down on for it.

Anyway, it hit me again this week; not on a yacht or over a thousand pound bottle of wine, but drawing one of my frivolous vapid pointless trees in my notebook with my cheap £4 pens. It hit me like a bullet train: I wasn’t failing or stupid, I was just choosing men who would always look down on me.

Of course they would: I’m half their age. I don’t have their experience, their worldviews, their assets. I don’t have their positions, their power, their outreach. I was just some fun. The 28 year old dolly to play with. I was never going to be able to be what they wanted because I wasn’t what they wanted. I just wasn’t millionaire Miranda from Morgan Stanley or post-Cambridge Clarissa from HSBC.

I was hurting myself. I was putting myself in situations where I wasn’t good enough. Or at least, not enough for someone far, far above my station and level. I, like my unfortunate ancestors before me, were white trash mistresses to be neatly discarded when a woman of that class, that world, turned up.

You’re not part of my world, one man had said drunkenly to me over a glass of white wine. You’re just not part of my world.

He was right.

I’m sure I’ll find someone: but I’m not hurting myself anymore. I don’t want anyone who doesn’t look at me with the same wonder and delight that I have when I look at them. I don’t want anyone who doesn’t reach for me as I reach for them. I don’t want anyone who views me as filler, as temporary, or a bit of fun. And I don’t want anyone who thinks I’m lesser, insignificant, or just flesh to them.

Sure, I’m still a nobody country girl and I doubt I’ll be more than a name in a census to history.

But I can choose someone, on my level, who loves me eye to eye, not down the end of their nose.