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A Date With the Handsome Former Colleague Who Proved Business and Pleasure Don't Mix

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One shouldn't mix business with pleasure, they say, but it is a redundant cliché. Many of us needn't be warned: the only pleasure a lot of people take from their work is skipping right out of it at 6pm. If you are the kind of person who derives gratification from their metier, it's unlikely that you'll need to find it in the groins of your colleagues or other pursuits in the workplace. As tantalising as Ken from the High Wycombe office may be, there are much more exciting temptations awaiting you outside the revolving doors of Day Job plc.

I've never had the misfortune to date anyone from the workplace and I've no intention of dipping my toe in that stagnant pool now, so it is with some bemusement I accept an ex-colleague's invitation to go for a drink. When he contacts me - over LinkedIn, Facebook's serious, data-obsessed, social leper of a sister - his message is fairly straightforward and not particularly chatty. It's hardly blokeish, but it's matter-of-fact. How have I been? Would I like to go for a drink?

I have no gaydar to speak of. Usually I don't realise a guy is my way inclined until he has his hand on my rump or his tongue down my throat. Plus, I've seen the back covers of enough chick lit novels to know that workmate-dating is right up there with having sex at a funeral when it comes to inappropriate things to do, but the working relationship is over and, crucially, I misread his invite. I'm uncharacteristically unprepared, and really quite reluctant to go at all, but I have an evening to kill and sitting at home stirring the cherry in a cocktail only looks good on TV. So I say yes, assuming he just wants to talk at me about his workplace woes or his girlfriend. The usual.

He opts to meet in a noisy bar in Soho. I arrive first, annoyingly, and sit doodling in the condensation on my pint glass as I wait. I try to remember how much I had to do with my date when we were co-workers. The answer, I discover after totting up the encounters in my head, is very little. Aside from a cursory "hello" in the kitchen as I plunged yet another tea bag into a cracked mug, plus one fateful time he was on the panel for a presentation I gave, our meetings have been few and far between. He always seemed like a nice guy, though, and I excitedly think that there may be some career opportunities coming my way. Maybe he saw something in me at our previous job that he wants to exploit wherever he is now. It isn't long before I discover exactly what he saw in me, and how he plans to get it there.

I check my watch, idly wondering what drink to order next, when he arrives in a flurry of activity. He apologises profusely for being late (a whole three minutes) and plonks his bag onto the table, making the entire thing wobble, as if he's diffusing all his nervous energy into it. As I can't get a word in edgeways, I have plenty of time to scope him out and I do so, but not too obviously; after all, at this point he's a straight colleague and this is a business meeting.

He's much more attractive than I remember, dressed sharply as if just out of work and, judging by the oppressive cloud of cologne, via the nearest branch of Boots, too. He scurries off to the bar to buy us drinks and there's something about the glint in his eyes - deep dark brown and sitting beneath what look suspiciously like shaped eyebrows - which makes me think we are not just here to talk about spreadsheets. Let's not elaborate on that and turn it into a pun; we're better than that.

In a whirlwind, he is back at my side, his eyes flashing again. He sits very close to me, his thigh not quite touching mine but you would be hard-pressed to get a grain of salt between them. He's off talking again, but he is at least asking me questions rather than burbling his way through a book report like most of my dates do. His first question is a jugular-seeking missile about when I last had a serious boyfriend. Finally, the penny drops.

"About two years ago," I reply, moving in a little closer now I know what game we're playing.
"So you'll be looking to settle down soon, I guess?"

My, he's fast. I explain that I'm not, and just enjoying being single at the moment.
"Oh right, I just figured, y'know, 'cos of your age and stuff," is his reply. If he means to wound with this barb, he shows no sign of it. Yet with just a casual remark and a swig of his bottle of Beck's he has swaddled me in a mauve bedjacket and hurled me into an adjustable bed with a side table, upon which sits a scratched glass containing Steradent and a set of false teeth.

I shift uneasily in my chair and my bones creak in sympathy. He is all of five years younger than me, for crying out loud. I don't let me discomfort show and instead resolve the best way to avoid him mortally offending me is to get him to talk, so I ask him a couple of questions about his work and what he's doing now.

He's moved on from our old place of employ, he tells me. His boyfriend at the time wanted him to make a change and so he left his job to start anew. I'm torn between admiring the sacrifice he made and questioning his decision to submit to his ex's request. I tell him this and his face sets, his eyes becoming lifeless until we change the subject. He decides to talk about how old I am again. He's fascinated by my age, quizzing me on cultural references and asking what it's like to be a gay man of "my generation". I briefly look over to the pub window to check my reflection to make sure my hair hasn't gone bright white and ask him what the deal is with this age obsession.

"Single gay men just seem to end up alone and bitter when they get old," he confides. "I don't wanna be like that." I'm puzzled."I think you're hanging around with the wrong gay men."

It seems crass to point out that young gay men can be just as lonely and bitter, if not more, than their silver-haired counterparts, but I do anyway and he turns to me, all handsome and clueless, and tells me that every gay man he's been with has fucked him over one way or the other, and that he doesn't think he can ever be in a relationship. I'm not altogether sure why I'm here, but I feel like an actor at an audition that's just taken a turn for the worse.

He then kicks off a monologue that lasts a good 20 minutes, drilling down in great detail about all his "boyfriends" - he counts one night stands in this group - and their list of crimes. Most of their misdemeanours seem petty and overblown, aside from the unfortunate suitor who ran over his dog as he was making a quick getaway after a night of passion turned into an argument. Perhaps realising he is losing me with his 'woe is me' act, he speedily changes his line, attempting to paint himself as an ultra-desirable god that I simply must be with. His method is to tell me about two ex-boyfriends who were madly in love with him, how they begged and pleaded for him to first of all be with them and finally never leave them. There were tears, flowers, holidays in five-star resorts, weekends in the country and champagne - endless, abundant glasses of champagne.

"So what happened?" I ask, perfectly reasonably, my neck starting to ache somewhat as I have been trying to tilt my head at an angle which makes me look interested. "They both cheated on me," he says, "but little do they know I did the dirty on them first!" He sits back proudly and rubs the rim of his bottle with his finger.

He then carries on, talking me through the break-ups and inevitable division of goods and finances. I realise that in the entire time I have been sitting here, all he has talked about is his ex-boyfriends. And his only line of questioning to me was when did I last have one.

I look at him again. He really is beautiful. He seems odd out of the workplace, though, like an iguana sitting on a flowery sofa. I'm not used to seeing him as a real person, with thoughts, feelings, gripes. My eyes wander down from his face to his neck to his body and everything is perfection, save for a speck of dirt on his collar.

He will age well, I decide. But I don't want to be there when he does. His insecurities, at the moment only a speck, will grow and grow the older he becomes. Those hang-ups about age and men will strain and he will look for the nearest person to blame. At the moment, it's someone else - he is gleefully telling me how he refilled his ex's vodka bottles with water - but if I stand too close for too long, it'll be my turn. I am fading fast and definitely too old to waste any more time listening to him. I drain my drink and make up a previous engagement. He shrugs and nods, apparently insouciant at my departure.

I bid him adieu and make my way out onto the street, knowing that his next date is likely to hear the story about the superannuated ex-colleague who wasn't ready to settle down. Ah well, I never did like taking my work home with me, no matter how much pleasure I could've got out of taking care of 'business'.

Stats: 5'9", 31, brown/brown, London
When: Winter 2012
Where: Soho, London
Pre-date rating: 8/10
Post-date rating: 6.5/10
Date in one sentence: A workplace honey talks the talk yet fails his performance appraisal.

A truncated version of this post first appeared in GT magazine, where I write a monthly column about my dating experiences. Find out when the next issue is due on the GT website.

Around the Web

When Love And Work Collide - AskMen

When a colleague becomes a lover - Life & Style - The Independent

Six Tips for Dating a Colleague - Yahoo! Voices - voices.yahoo.com

How to Date a Coworker - Dating Coworkers - Cosmopolitan

Boss's Memo: Go Ahead, Date (With My Blessing) - New York Times