This weekend, one of my roommates turned 21. In true good-roommate fashion, the rest of us threw him a party. The theme? Oregon Trail. Brilliant, I know. We decorated with pictures of oxen and screenshots from the computer game and even hung a tapestry from the ceiling like it was a wagon cover (or wagon “tongue” in the game).

To fully prepare, I downloaded an old copy of the 90s computer game. My roommates, a few friends and I stared the possibility of frittering away a Friday night in front of the computer screen in the eyes. We joked about losing sleep and not showering because of time spent “on the trail.” They were the kinds of jokes that were funny because they could be true.

I started the game and forgot to enter any names other than my own, meaning I played and lived with Mollies and Abes. We bought our supplies sensibly, not stocking up on bullets despite our great want to. We traveled only at a steady pace; our rations remained filling. Too many men and women had been lost in our past travels to do otherwise.

We hunted only when necessary, and didn’t kill much more than we could carry (the little boy instinct of destruction remained, but had calmed). We caulked our wagon to float over the rivers, the safe, lame option, rather than fording them all but one time, and we didn’t die.

We reached Chimney Rock and Independence Rock and all the “landmarks” on the way. We had signs telling us we were close to the end, the Grande Ronde river, even though we had only been playing for a half hour. We disregarded them and waited for snakebites and sick oxen.

They came, but went just as quickly. An ox may have died, and our water gone bad, but our health remained “fair.”

Then, the big deal. We hit an unnamed river and we’re given the option of taking the toll road (for sissies) or rafting the river. My friend Pat (Smith, of Pat Smith Reads the News fame) manned the controls, I was the back-seat rafter and two others watched on. It was hectic, as large rock formations came at our wagon/raft combination, and the controls were tough, the game having been invented before most laptops. I was shouting ‘lefts’ and ‘rights’ most of the time, though Pat’s rafting skills had apparently not declined with age. We reached the end of the river, “pulled our wagon ashore,” and with that, the game was over. We got a congratulations screen and found out that we didn’t make the List of Legends.

Where was the challenge? Before playing, none of us could remember anyone having made it to Oregon. It took us about 40 minutes, roughly as long as one of my elementary school computer classes where the game was employed as originally intended. The finish of the game was worse than anti-climactic, it caused me to reevaluate my grades three through six education and even my childhood.

My generation (Y) and the one preceding it (X), have turned nostalgia into an art-form. VH1 gave us “I Love the ‘70s” which were at least distant enough to deserve some wistfulness, then “I Love the ‘80s,” and, not even five years removed, “I Love the ‘90s.” My sister has a Trivial Pursuit game of only 1990s trivia. Trivial indeed.

TV Land, which used to air shows my parents grew up with now shows things that I remember watching when they aired the first time. I remember them being better too.

I think this is my problem with the recent nostalgasm—it’s natural to remember things as better than they were. It’s why people go to high school reunions or have second marriages. Life would be a lot tougher if every misstep were remembered as clearly as every triumph. A squeaky-clean memory may be great for a court of law, but I think that may be all. A magnifying glass to the past will also magnify what wasn’t so great.

And it took 2000 miles to find out.