My friend told me the other day that he approaches relationships with pessimism. When I asked him what he meant, his reply was, 'How many relationships have you seen succeed? The odds are stacked for failure'. He said this as he sat on my bed, topless and twiddling my hair...when I say my friend, I mean the guy I'm currently dating.
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It's been two years since I packed up the last of my belongings from the flat I shared with my ex. It was surprising how little I had to take, still I left much behind; the horrid plastic Christmas tree and decorations I thought would last forever, the paintings we'd made when we first moved in and the never opened pack of condoms in the bathroom cabinet. It was an ironic reminder of the pointlessness of our last few years together. The tightly wrapped cellophane box taunted me from the bathroom shelf. I'd not had a proper kiss in years, and couldn't even remember what sex was like, let alone good sex! But as excited as I was, I felt a stab of fear, I was twenty six and hadn't been single for longer than a month, two at most since the age of 16.

Two years on, I can safely say that dating in your late twenties is a whole different ballgame.

My friend told me the other day that he approaches relationships with pessimism. When I asked him what he meant, his reply was, 'How many relationships have you seen succeed? The odds are stacked for failure'. He said this as he sat on my bed, topless and twiddling my hair... when I say my friend, I mean the guy I'm currently dating. It went from friend to boyfriend so quickly that I was spinning, and my usual 'is this guy good boyfriend material' stop-check never really happened. Let's for a moment ignore the fact that this isn't what a girl wants to hear from her boyfriend, and examine the point... because there is one. Do we learn and grow from each failed relationship, or learn and shrink?

I've often wondered whether the notion of growth is a comfort blanket with which we soothe ourselves into thinking that next time we will know to avoid Mr. Unavailable, Monsieur Immature or the little lost boy that never quite found himself. But what if it is in fact the opposite? What if every time we say 'next time he won't have X' or 'next time he will be more Y', we create a formula that's impossible to crack? Perhaps Freud is right in his claim that the 'archaic reaction has, so to speak, exhausted itself in the first object'. Ergo, 'The One' is synonymous with our 'Number One'. If so, what does that mean for me and my 'Number Six'?

The odds of this relationship succeeding were never great; he lives with my ex (Number Four incidentally) I live with his ex. Sometimes things just happen, and when they do, you go for it. But five weeks in, the doubts are already buzzing at the peripheries like those annoying barflies that zip about aimlessly and achieve absolutely nothing.

But when do you know that enough is enough? And are we giving up too fast? An online survey of top reasons to dump a guy revealed some expected and some...not so much.

Cheating (like having an affair with her friend, or sleeping with her sister, or fooling around with every girl he meets)

(Fair enough)

He doesn't talk to her

(Silence, not always golden)

They eat all the food

(Could get annoying... especially in restaurants)

They think the TV is more important

(No one wants their relationship flatlined by their flatscreen!)

Porn

(???)

All very valid reasons, but sometimes it isn't quite so black and white. The problem with my Number Six, is that it isn't really that obvious! In the grand scheme of things, does it really matter that he cracks stupid jokes when I'm in the middle of telling a story? Should I be worried that he seems to have very little ambition and his literary diversions extend as far as the Sun?

None of this mattered when we were just 'mates'. Then, I loved how he uses every opportunity to Face-hack our friends, that he's a massive gossip and that he has a scatty way of bumbling about, getting distracted halfway through a sentence and laughing at something odd in a magazine. But my expectations suddenly morphed with the new title 'girlfriend'. Now, everything he is, everything he does, is a reflection on me. After all, no one wants to be the 'why on earth is she with him' girl!

It was time for the checklist to make an appearance, compiled over a decade of dating and promising an impossible man-topia. It was everything I wanted in 'The One' and almost everything 'The Sixth' was lacking.

With an aching brain, I leant outside the skylight in my attic room and smoked a cigarette. The train to Waterloo rumbled on the tracks opposite and as the sky turned dark, I remembered the first night he came up to my room, we'd hung out of the skylight smoking at four in the morning. I'd leant so far out that there was just him in front of me, and the outside air behind. It had felt like that scene in Titanic, the really cheesy one... 'I'm flying Jack' sounds silly now, but at the time I guess I was, at the time there was just me and him in the world. There was no checklist, or pressure, just the excitement of something new. It was an innocent excitement, and one that seems to fade faster and faster the further you grow from those teenage years. I realised then, that perhaps I wasn't ready to let it go away just yet.

Back went the checklist to the place from whence it came, tucked into the mental drawer labelled 'mum'. I might be 28, but does that mean I can't date like a 16-year-old for just a little bit longer?