A Date With the Nice Guy Who Always Finished Last

His profile promised the romantic equivalent of high-speed broadband. Instead he is, at best, alternately fizzing and flatlining dial-up on the Isle of Skye. He's telling me about his career thus far. It's light on comedy.

Is there anything less sexy than a date who dumps all his problems on you? Is it really only nice guys who finish last?

Internet dating attracts the loneliest of souls. Behind every profile advertising a "vivacious go-getter", there's a self-doubting emotional wreck searching for a friendly face upon which they can offload their problems - and little else. Sadly. Thankfully. Everybody's got their problems; some of them like to share them on a supposedly romantic evening. It's a risky seduction technique, but depressingly popular.

Tonight, I'm playing shrink to Christopher, an aspiring novelist with faux-messy hair and a bowtie. Aspiring. Bonjour alarm bells - aspirations are doppelgangers of unrealised, far-fetched fantasies.

His profile promised the romantic equivalent of high-speed broadband. Instead he is, at best, alternately fizzing and flatlining dial-up on the Isle of Skye. He's telling me about his career thus far. It's light on comedy.

"I've wasted chances, fucked up opportunities, chased stupid dreams that turned into nightmares and missed out on a podium place every single time. I try not to be bitter about it, but it's hard. I wish things were different. I wish I wasn't such a, such a..." he begins to stammer.

I eye my beer wearily.

"Such a what?" I prompt.

He sighs heavily. Any joy remaining in the room is quickly sucked out of it.

He continues: "Such an also-ran. A bystander. I've never been at the centre of anything. Always in orbit. Uranus."

I do the obligatory schoolboy laugh, but he ploughs on, deadly serious. "I wish I'd been less of a loser."

I begin to wish he hadn't ordered that gin and tonic.

"You don't really feel that way about yourself, do you?" I say.

He looks up from the table, his eyes sad and grey, like the unluckiest pensioner in the bingo hall.

"I'm afraid so. I try and try but nothing seems to work. All my relationships have been a disaster. Men screw me over all the time."

He's doing a dreadful PR job on himself. What am I supposed to say? I have never met him before; I only have his side of the story. If he was this scintillating on dates to other men, no wonder all they wanted to do was roll in the hay and run. Do nice guys all really finish last? Or is there a reason you're destined to be runner-up? I'm not sure I want to find out, and he doesn't look like he needs psychoanalysing. Just a hug and that gin taking away from him would do, I reckon.

We haven't known each other long enough for physical contact, so a verbal ruffling of the hair will have to do.

"I'm sure you've just been unlucky," I offer.

He looks down again, utterly convinced. "Yeah, maybe."

A huge sigh. His eyes return to mine. "Not much chance of a second date, I suppose?" he says.

My mouth dribbles into a weak smile. I feel celibacy's icy fingers grip my balls.

"I think you've just had a bad day. Let's try another, some other time." It feels about as sincere as a Christmas card with a live grenade attached.

"Thanks," he says quietly, and we finish our drinks before heading out into the night and away from each other.

Over the next few days, I think about whether to contact him again. Sure, he was a bit of a downer, but maybe he'd had a bad day. And while he'd been screwed over by men before, perhaps I can prove we're not all the same. Considering those vulnerable eyes, I finally do contact him - a text proposing a drink.

I wait. Nothing comes in return that evening. Busy, maybe. Out of the country. And, then two days later, my phone buzzes.

"Nice of you to get in touch," comes the reply. "But I kind of got a better offer. LOL. Was nice to meet you. Take care."

Maybe I should be irked, but I'm not. His curse looks to be finally broken. Second prize now belongs to me.

Stats: 35, 5'8", brown/grey, Shropshire

Where: Columbia Rd, London

Pre-date rating: 7/10

Post-date rating: 3/10

Date in one sentence: The world's biggest loser wins the lottery.

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