Most dates are neither good nor bad but simply fine. This I find depressing

Friends tell me that online dating requires practice; that I will become less invested each time. But who wants to feel less?

By Pippa Bailey

On the many times I have expressed concern over the past year that this column will now always be A Break-up Column, that day’s chosen confidante has often replied with something along the lines of, “Don’t worry, soon it will be a dating column.” I’ve resisted for the four months since I started “getting out there” again (a masochistic way to start a New Year, I know) because the road between here and being billed as a “sex writer” on panel discussions is both short and slippery. But dates have been had, and there are column inches to fill.

When I first wrote about the end of my relationship, I was a long way from considering how this column might play at the start of another. I have learnt that, despite what they might say, men google love interests just as much as women do – and that apparently it is possible to find this column knowing only my first name and my profession. Many men, having done so, profess that they feel like they know me already, as if the version of myself I share in these pages isn’t just that – a version. Most are kind enough to promise they won’t read too far back; they’d rather hear it from me. I suppose I invite it: my dating profile says, “Can’t promise not to write about you.” (I like to think of it as a way of filtering out those men who might be uncomfortable with this particular quirk of my life – though I realise it may also attract narcissists.)

Dating apps make me both judgemental and spectacularly fussy. I discount men for tiny details I wouldn’t notice in real life: living in south London, weird eyebrows… There are major – and, I think, more justified – “icks” that mandate the left-swipe, too: topless gym selfies; golf; raspberry-red chinos; men whose strongest opener is, “Hey, how are you?” So much of what makes someone characterful, and therefore attractive – their voice, their stance, the animation of their face – is lost when an individual is compressed to a few photos, a few artificial witticisms.

I often encouraged friends, back when I was a smugly coupled-up person who didn’t know what she was talking about, that there was nothing to lose from going for a drink with someone new: you’d come away from it with either a good date or a good story. I have been on just one first date this year that wouldn’t have been out of place in a Hollywood film: we bounced off each other in conversation to the extent that neither finished a single story, and snogged on the pavement having been kicked out of the pub at closing. It didn’t last, for reasons I’m still not entirely clear on, other than – roll your eyes with me – men. The rest weren’t comically bad (if they were, you’d have been reading about all this weeks ago); they were simply average. This I find the most depressing.

I am not a generous enough person to think of dating as an opportunity to meet new people, to do fun things; I already have plenty of friends and plenty of fun, thank you very much. I am trying to rewrite this script, to think of dating as being like work experience: even if you hate a job, you have learnt something about yourself, what works for you and what doesn’t. I surprised myself recently by saying “Why not” when a man I’d been on a couple of dates with asked if we could just be friends. (At one point during what turned out to be our last date he googled the closing time of the pub we were in and then said, “You’re going to write about this aren’t you?” Consider this me giving the man what he wants.)

Dating online, rather than waiting for a real-life meet-cute, may give a higher chance of meeting someone, but with that comes a higher-than-average incidence of rejection. Friends tell me that it requires practice; that I will become less invested each time, and therefore be less hurt, less disappointed, when it doesn’t work out. But I am not sure that hardened, desensitised, is something I want to be; who wants to feel less?

I swing between wondering if I’m not ready just yet, whether I need more time to heal, and believing that “getting out there” is part of the healing. Perhaps both can be true at once. Maybe I should take a break from dating, just for a little while. Or maybe, picking up my phone, just one more try…