Not so much the bet as the payment...
I was in a society of reprobates at University for whom the traditional bet was a bottle of Port. This could be bog-standard tawny at a few quid up to your proper vintage stuff if you really meant business.

One particularly drunken evening a friend of mine was "reading grace", which amounted to standing up at the beginning of dinner and mumbling something random in Latin. Having already hit the bar pretty hard by that point, I come up with an idea for rendering that somewhat tedious artifact a little more interesting "A bottle of '72 vintage (his birth year) says you won't sing grace to the tune of the club anthem (a well known tune subverted)". Being a sport, my friend proceeds to do this, in front of staff, fellows and several hundred students.

The issue now is payment. Those of you familiar with port vintages will probably even now be crying "but '72 was not a vintage year", but in fact it was. Unfortunately, it was a very poor vintage and only a few "houses" declared it a vintage year. At the time of this bet, Berry Bros had a '72 on their list, but by the time I came to order it was not available.

Now such bets may be suspended, but they are never forgotten and over the nearly 10 years that followed, I occasionally looked out for sources of '72 vintage but never did I find one. I tried all the wine merchants I knew of, specialists port sites on the web (including many based in Portugal itself) and routinely asked in independent wine-stores I passed, but to no avail.

Never, that was, until a week or so before we were to meet up at an anniversary dinner, when much dedicated googling finally identified a single bottle available from an obscure wine-supplier's web site. A site so small that they actually had the number of bottles left listed next to each item. Paypal account duly raided (they were too small to take visa directly) I attended this debauched get-together with my debt-payment finally in hand, wrapped discretely in tissue-paper.

Dinner and much wine was had before it was time for desert and therefore for Port. Retrieving what appeared to be the last bottle of '72 vintage available for retail in Europe, I presented this with much ceremony to my friend, who confessed having given up on ever receiving payment since he too had seen ne'er a single bottle in the intervening years. Conscience finally cleared I wander down the table to see some other friends only for a great wailing to break out back a-way.

I could have cried. There, dumbstruck with horror, is my friend, staring at a pool of crimson liquid slowly spreading from a sad pile of dusty green glass. His table-neighbour, making some point or other, having swept out a hand and with it propelled the fruits of my decade-long search onto an unforgiving stone floor.

So, ladies and gents, should you ever be the recipient of a eminently frangible long-awaited debt settlement, for gods' sake open it there and then. The alternative is simply too painful.
( Ugi , it's a game of give and cake, Fri 8 May 2009, 15:53, 3 replies)

Oh Lord!
As a fellow Port-head, that is a sad story. '77 is the one for me, though I have a '70 tucked away (my birth year). I tracked down a '44 for my dad, and he had the indecency to drink it on his 65th, whilst I was out of the country!
(Mousy Tongue ...Generally bemused by life..., Sat 9 May 2009, 2:08, closed)

We were mostly drinking '77 that night...
.. and it was great. It was a 50th anniversary, so we had a little of the '54 which was good, but not as good as it had been 10 years earlier at the 40th dinner. 40 years seems to be long enough.

A random port story - my wife is not usually keen on port, but went to a college reunion dinner and said to me the following morning that the port the previous night was "quite nice really". Turns out to have been Fonseca '63! Quite nice? No shit.
( Ugi , it's a game of give and cake, Mon 11 May 2009, 9:42, closed)

Lucky
I was lucky enough to be drinking with a vintner when England drubbed the hun 5-1 in 2001. To celebrate he opened a bottle of 1966 Port. Couldn't tell you what it was but it was very acceptable.
(porkylips looks better as the sun goes down., Mon 11 May 2009, 12:35, closed)