#51. Hedging Your Bets (Tuesday, June 14, 2004)

What was your best day…of feeling a huge weight slide off your back?

Part 1

In the world of finance, there is this concept of hedging – buying a security (e.g. a stock, an option, etc.) that’s expected to move in the opposite direction to a security you already own. So that no matter which way the market moves, you’re protected against a loss.

Word to the wise, though. Leave the hedging to financial markets, and out of real life.

In this instance, I was making a bet with my eighth-grade best friend Damien Bei (#121). To hedge away my insecurity that a certain classmate of mine – Todd Xing, with whom I had been best friends last year before our relationship disintegrated in a spectacular way a few months before – would score perfect on the Gauss math contest¹. (And thus “surpass” me, since I had been the only person in the school to score perfect the year before.)

The bet terms were simple. If Todd gets perfect, then Damien has to do anything of my choice. If Todd doesn’t get perfect, then I have to do anything of Damien’s choice – and we both knew what that meant.

And, as could be totally expected, Todd didn’t get perfect².

Samantha Wisniewski was the first girl I ever had a real crush on. And looking back, I have no idea what I was thinking: she was a foot shorter than me, not a particularly promising student, and from second-hand accounts – I never actually spoke to her³ – not a very nice person either. Either way, thirteen-year-old me was smitten; but had no plans to actually do anything until the lost bet forced my hand.

This was back in early May, and it started with a two-week deadline to ask her out. Being the socially awkward kid I was, I didn’t even come close the first week, thinking it would get easier as time went by. Not so at all. The first Friday, I felt like shit going into the weekend. And the next Friday was even worse.

I guess Damien decided to have some fun with it and torture me some more. He started offering “extensions” in return for minor things – onion pancakes, editing his English essay, and ringing on strangers’ doorbells. And as the weeks piled up, I clearly had no intention of approaching that girl, although it seemed like I had a chance at least three times a day.

This went on all the way until mid-June. And this fateful Tuesday.

The majority of us (but not Damien) were leaving on a three-day trip to Quebec City the next day; so I would have to deal with it that day or else have the entire trip ruined by this issue which was close to becoming a mental illness.

As luck would have it, just as we were leaving school I saw her with her friends at the entrance. Drawing from some (for me at least) amazing courage, I walked up. Keep in mind she had no idea who I was.

“Hey Sam. Hey Sam, um, you want to go out with me? Uh, you wanna go out with me?”
“No, not really. Sorry about that.”

We all know that flashing lights feeling when you do something crazy that instantly relieves a ton of pressure (#87). This was followed by her friends – one girl who’d been expelled from Shangyu’s old school, and Chris Calhoun who’d gotten suspended earlier this year for initiating a fight with our classmate Wesley – coming up to see what happened.

I was sure I was about to get my ass kicked, but I ended up just talking with them (but not Samantha) for ten minutes about the upcoming Quebec trip. It was weird. And Damien and Shangyu were just standing close by enjoying the show.

Of course, when that was all done, all I could think was: That wasn’t so bad. Why the hell did I not get that over with sooner?

Part 2

With that nerve-wracking situation now resolved, there was no way this three-day trip to Quebec City – my first overnight school trip – could not be amazing.

That said, the entire time I was paranoid of running into Samantha. But besides briefly seeing her when getting on the bus (and looking the other way as fast as I could), I managed to avoid her for the better part of the trip.

Either way, our first night in Quebec City was dinner and a dance aboard a cruise ship. The highlight of that was getting Shangyu (Mr. Serious) to dance with a girl. As well as seeing Nigel Healey (Mr. Genius, #62) get with the girl he liked. (Or rather, the girl, Darla, I claimed he liked, then told everybody until it became true.⁴)

The best part of that day, though, was when Shangyu, Nigel, Todd, and I unlocked our hotel room to find that it was twice the size of anybody else’s. And that night, while we were watching Euro 2004 Portugal vs. Russia, I caught Nigel in a rare moment of weakness when he thought Casablanca was in Italy. I never let him forget that.

The next day at lunch, after I ate all of Derek (#123, #103), Steven Fennessy, and Noah’s leftover ham and cheese crepes⁵, we had two hours to ourselves in Quebec’s Old Town. So the four of us went to tour the shops. At the time, Derek had a girlfriend and Noah had a girl he wanted to be his girlfriend. So they were hunting for presents.

Of course, Derek had forgotten to bring any money. And he really wanted to buy this dolphin ring thing. I happened to have ten dollars I wasn’t planning to spend, so I lent it to him.⁶ Then it was Noah’s turn. And I got him to pick out this cheap pink stone necklace. Hey, if I couldn’t get what I wanted, at least I could help my friends out, right?

As it happened, we ran into Derek’s girlfriend soon after. She was thrilled with the gift, and he quickly left with her. A few minutes later, Noah’s girl. Same thing. So in the end it was just Steven and I, joking about the two lover-boys as we wandered the shops for the last hour.

Another fun bit was during that evening, when Nigel and Shangyu disappeared while we were taking group photos – and showed up a few hours later on a theater stage dancing to Beyonce’s “Crazy in Love”. Nigel had some decent moves, while Shangyu just stood there stoically without moving for the length of the song⁷.

Given the circumstances, seeing half my friends get girlfriends should have made the trip a total disaster. But looking back, the only thing I can think of is how well I got along with Steven.

Up until then, I had known Steven for three years and we always had a volatile frenemy thing going on. We shared a lot of interests, but he would have his jerk moments from time to time, and I would always overreact. But in the months preceding, it seemed like both of us suddenly matured. Hanging out with him on the trip made me realize how it had evolved into a friendship, and a truly special one.

Of course, Steven went to a different high school and ended up following a completely different path, and I have not seen that guy since. But the way we worked through our differences was one of the most important parts of my preteen years, and probably his as well.

This all might seem kind of messed up, but hey, probably par for the course on this page at least.

A exam of twenty-five math problems (the last five very difficult), managed by the University of Waterloo (#121), offered to high-achieving middle school students across the country.
To my immense happiness, at the time at least (I didn’t get perfect either).
I should note here that she wasn’t actually in my class.
I loved stirring up drama as long as it was not mine.
Something I did multiple times that trip, for multiple food items of varying levels of tastiness.
To his credit, he remembered to pay me back in September.
Which was enough to get him the full ladies’ man treatment for the rest of the night.