I have never been one for dating. Why anybody would want to put themselves into a situation that has a high probability of being tedious, boring, awkward and difficult is beyond me, but hey, some people seem to like it. Perhaps it’s the possibility for sex at the end of the night, or getting to try on lots of different people for size – whatever it is, it’s not for me. I don’t even try on clothes while shopping.

No, I’ve always been the sort that just kind of ends up in relationships – I’ve been an accidental serial monogamist since my teens, but it’s not as pathetic as it sounds as there have just really been two serious men in my life with a handy 12 month gap in between. During this single year, I believe I went on two dates with boys I met in college, neither of which were exactly successful. The first one was very sweet and I bathed in the glow of the attention and affection he fawned on me, having had my heart smashed into smithereens mere months previously. He took me to the zoo, and even bought me a pair of mittens because it was unexpectedly cold out. However while he was a gentleman and very sweet, I just wasn’t feeling it. Sure, we had the banter and a few kisses, and as we were sort-of friends beforehand it was never that awkward. Still, it wasn’t exactly comfortable. Especially when his nut allergy made choosing a place to eat complicated.

The second guy I dated merely for appearances, as I found him neither interesting nor sparky. I’d simply had a wholly physical crush on him for over a year, and wanted to feel desirable again. Then, by the time Eoin and I ended up going on an actual date, our relationship was already established after weeks of talking in his car and kissing in a nightclub.

As for work,  I spent four years in a monogamous relationship with the magazine I learned my trade on. Well I did have an illicit affair with the August 2010 issue of Company magazine, but I wrote under a pseudonym to make sure my cheating wouldn’t be discovered. And hey, I can talk about it now cos we’ve broken up, my old job and I. However, it was an amicable ending and we’re still the best of friends, which is more than I can say than any of my human exes.

I have now been a freelancer for three months, and am realising more and more just how much it is like dating – and dating New York style for that matter, juggling several relationships at once and not going steady with any of them. I am experiencing through work what I haven’t yet with men – dating I actually really enjoy, and want to do more of. Not only that, but I want to date even more than I already am, and different types too – monthlies, weeklies, glossy, not so glossy, websites, vlogs, TV, radio, broadsheets, tabloids, supplements and annuals – I want it all, baby. As they say, variety is the spice of life.

However, there is a downside to dating in multiples. I have to be constantly on my game, never prioritising one over another, or pursuing a conflict of interests. When in several open relationships, trust is always an obvious issue. As well as all that, my Filofax can be worryingly full one week, and terrifyingly empty the next. Sometimes one date is all over me, and then suddenly silent for weeks – somebody needs to write The Rules for freelancing, never mind dating. What if in a few weeks, nobody wants to professionally date me and I’m left on the shelf? The thought is far more chilling than romantic singledom, let me tell you.

There’s also always that little birdie that you have your eye on, that teases and tempts you, but with whom you never quite manage to seal the deal. A real man could be flirted into submission unless taken or made of stone (hey, I’m convincing), but I’m afraid my professional coquettishness is not yet quite as finely tuned as my own personal brand of seduction. I’m also solely reliant on my brain when it comes to freelance dating. Although I like to think my wit and charm make up the biggest reason why a man would like to take me out, a push-up bra is not as helpful in my current scenario as it might be in dating reality. Plus, I am obviously a strident feminist, and would never use my wiles to get ahead – my imaginary best friend Caitlin Moran would disown me.

My charm has to come through email, phone calls, coffee meetings, and fabulous, life-changing ideas (which believe me, are harder to think up than funny date banter is), because nobody gives you prized freelance budget money for mediocre. Sure, there are days when I’d like a cosy, long-term professional relationship again; when the fear of dating gets too much and I imagine the security of a relationship. But then a little hottie walks on by, and I know I’d be a fool not to chase it down the street… if you get my drift.