I looked wearily at the masses of people that had packed the waiting area outside the plush ballroom of the Ritz-Carlton Hotel.
It was 7.30pm and the doors should have opened half an hour ago. I felt a minor irritation come on as I scanned, for the tenth time, the leaflet that detailed the night's programme.
Who on earth are these people that I am standing in line and waiting to see?
It was the second night of the Youtube FanFest, "designed to give fans and digital media professionals an opportunity to get up close and personal with the stars who are driving the global YouTube ecosystem".
I was there only because a good friend asked me in the morning if I could get tickets for something or other at the Ritz- Carlton that night.
"The what?" I asked distractedly.
"It's called the you-tube fan-fest," he said, enunciating the words slowly, as if speaking to a child.
"Boyce Avenue are playing and I found out about it too late. There were free tickets online but now they're all gone."
I may not know that much about Boyce Avenue but I knew that it was one of his favourite bands, so I begged a colleague at the newsroom to work some magic at the last minute, and we got in.
It turned out that the band was only one of nine acts scheduled to go onstage that night. I scanned the list of the others.
Aside from British electro-pop singer Little Boots, who had a UK hit album three or four years ago, I had absolutely no idea who the rest were.
There were a few other singers - a Dome Pakorn Lam from Thailand, a Joseph Vincent from the United States and a group called GAC from Indonesia.
There were also some "Internet personalities": two Canadians living in Korea that have become famous for making videos about K-pop and K-culture, an Indian creative collective with global dreams for their clever clips and a young Hawaiian chap who films stunts and gags with a bunch of neighbourhood friends.
They even flew in a chef called Rob Nixon whose Nicko's Kitchen video clips are among the most popular cooking programmes in the world. Apparently, I had missed another Japanese lady chef the night before who cooks with a grey French poodle called Francis that "narrates" her videos.
I started to feel a bit uneasy. All around me, the young people that were in the queue were chattering non-stop about these names that I had never heard of before.
Five girls behind me were trading anecdotes about their favourite Ryan Higa scenes as they dropped out from the queue momentarily to take carefully posed group pictures.
I ordered a beer from the bar and nervously sipped at it. I looked to be the only one in the crowd who was doing that.
I took out my phone and stabbed at it in an effort to look like I was fitting in, but my Apple looked woefully out of place in a sea of shiny new Android smartphones.
Later, when the programme had finally started, I looked over at the boy next to me who had come with his friend.
He looked to be about 12, but he was switching apps and flinging those "live tiles" around his Windows smartphone with ninja-like speed.
Onstage Joseph Vincent had barely gotten to the chorus of his first song and this little man had tweeted, Instagrammed and Facebooked the pictures he had taken of the singer; all while simultaneously checking various e-mail accounts and chatting with two or three friends.
The uneasy feeling I had felt early in the evening swelled into an uncomfortable moment of self-realisation.
I looked up at the ballroom - at the manic screaming that greeted a bunch of amateurs, the sea of smartphones raised high, the swinging video cameras that were streaming live online, the staccato 15-minute chop-and-change of the evening's proceedings - and wondered if the inevitable moment had come.
The moment you realise that you are no longer modern or contemporary, that you have finally crossed the line that separates the new from the old.
For days after the event, I kept playing a song - probably the same vintage as smartphone wonderboy - by musician and DJ James Murphy over and over in the car.
"I'm losing my edge to better looking people with better ideas and more talent, and they're actually really, really nice," sings the 43-year-old American in a panicked, slightly hysterical wail.
He proceeds to name drop every cool club and event he has been to, every band he knows and all the records he had "before everyone else" in a wild crescendo of words.
But he ends up bitter, admitting that he is always hearing that someone else is doing something newer, better and hipper.
"I hear that everybody you know is more relevant than everybody I know," he concludes, sounding defeated and lost.
This should be unsettling territory for me.
Growing up a skinny kid in school with a medical problem, I fashioned a reputation for always knowing what was cool and hip into a sort of shield for my physical insecurities.
I voraciously consumed magazines - and later websites - on music, fashion, technology, pop culture and the arts.
I was the go-to guy among my colleagues and friends for the latest must-have phone or album. I always seemed to have the jump on the best TV shows that have yet to hit Singapore.
Yet as I hit my 30s and settled down in my life, my circle of friends - and interests - got smaller.
I sensed that I was losing touch with all that was new and happening and starting a slide into dinosaur territory.
I have felt James Murphy's panic in mid-conversation - a video that everyone has seen but me, an app that everyone is using - and rushed to the Internet to try and paper over knowledge gaps.
But the real test of whether you have truly becoming an old fart, however, is not how far you have slid down that slope.
It's whether you have the energy or the inclination to even care.
And that to me, sadly, was the real import of that one night of feeling alien at the Ritz-Carlton.
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