Quit playing games with my heart

You'll recall that date two with the lovely Kate went rather well: a nice drink in an out-of-the-way pub rounded off with a tentative but tingly kiss. We then indulged in some high quality texting banter, during which a topic we'd discussed in the pub came up: board games.

We shared an affection for board games, particularly Monopoly. I loved Monopoly as a child, possibly too much. In fact, I've tried to give it a wide berth since the ugly scenes that followed a demoralising defeat to my nan aged 11. My dad hated Monopoly and always said it "brought out the worst in people". The vicious, tearful abuse I levelled at dear Nana after her shock triumph seemed to back his theory up. Still, I retain a soft spot for the game and so did Kate. It was suggested in our texting flirtations that our next date should be in a pub, with board games, where we could play Monopoly. Great.

We met up 10 days after our second date. Kate confessed to having a hangover when I arrived and seemed slightly aloof, I thought. I wasn't sure if we would actually play Monopoly - it was just banter, really - but when we arrived at the pub in Primrose Hill, Kate seemed eager to get started.

We started setting the game up and it brought back happy childhood memories: Community Chest, £200 for passing Go, the little dog, the inexplicable iron. This was a great date idea.

Kate started the contest strongly, snapping up some prestigious properties. I was rusty but I bided my time and gradually revived the capitalist zeal that had fuelled many childhood victories. Soon I began to take control.
It occurred to me at one point that I should let Kate win. That's what I, as the man, was supposed to do in this situation. After all, Monopoly was just a pretext to bring us together — a romantic ruse. The result itself was unimportant. But my 11-year-old self would have happy slapped me for such insouciance. And anyway, what kind of self-respecting girl would give two hoots whether she won at Monopoly. I would play to win.

So I put into action my master plan. If you're interested, the way to win Monopoly is to buy the orange ones and the blue ones. People who think it's all about Mayfair and Park Lane are idiots, while anyone who buys the train stations should receive round-the-clock medical care, or failing that be put down like an old horse. This I knew to be true when I was 11, and nothing has changed. But as I gradually built up an imposing presence in the Vine Street area, a terrible realisation came to me. It was one I'd had previously as a small boy but, in the intervening years, had forgotten. Now I remembered: Monopoly with two people is a mind-numbingly tedious activity.

[See also: 10 excuses for dumping someone]

Sure, we chatted as we played. And we drank — a bit. But Monopoly was the centrepiece, and it was a dull centrepiece. A variety of sensations can potentially ruin a date: mistrust, uneasiness, jealousy. But nothing is quite so terminally destructive to romance as boredom.

The expansive swagger of my march to victory stood in stark contrast to the quality of conversation, which became stilted amid the ennui of the never-ending procession though jaded London landmarks. I became uncomfortable and stopped being funny and charming. I just wanted it to end. But despite Kate offering to throw in the towel more than once, 11-year-old Dan felt adamant we should play till she was mathematically and emphatically bankrupt. And so we did.

Then we were able to chat freely, Monopoly was finally over. But its influence lingered. At about 9.30, Kate said she was tired and still hungover and we should probably go. I found it difficult to disagree. We parted awkwardly, making a half-hearted pledge to meet again next week. I stewed on it for a few days then decided it was worth one last shot. After all, Kate had made such a brilliant impression in our first two dates. I asked if she was free on Thursday. She replied almost instantly with the 'let's be friends' text.

It's too simplistic to blame this all on Monopoly. There were probably 20 other reasons why Kate didn't want to see me again. All I know is: she was keen. Then we played Monopoly. And then she wasn't keen. Which is shame because I actually quite liked her. On the plus side, hotels on Vine Street, Bow Street, Marlborough Street, Angel, Euston and Pentonville Road plus houses on the browns and the pinks send out a pretty resounding message: Nana, God rest your soul and that, but I'm back!

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