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{Note: The Madonna Timeline is an ongoing feature, where I put the iPod on shuffle, and write a little anecdote on whatever was going on in my life when that Madonna song was released and/or came to prominence in my mind.}

Her voice has never sounded better. Even in the bustling pre-Thanksgiving buzz of Logan Airport, I can hear her clearly over the headphones of my portable CD player (this was 1996). I am about to board a flight to San Diego, my emotional state is shaky at best, but when Madonna is singing one of the most famous Andrew Lloyd Webber show tunes of all time, ‘Don’t Cry For Me Argentina’, I pause to listen. There are storms moving in from the West, but the flight is departing on time. A heavy coat is slung over my arm, and I wish I could leave it in the cold of a Boston November. But I’m getting ahead of myself. The iPod has chosen ‘Don’t Cry For Me Argentina’ as the next selection, and while I was hoping we might get an Evita song at this time of the year, I suddenly feel ill-equipped to fully convey the sad connotations that this song evokes.

It won’t be easy,

You’ll think it strange,

When I try to explain how I feel

That I still need your love after all that I’ve done…

The Fall of 1996 found me living in Boston, and commuting to Waltham for my last semester at Brandeis. I had fallen for a classmate in my Literary Criticism course, and for a brief moment he seemed smitten with me. We shared a love of musicals, the cute guy at the Boston Chipyard, and my impeccable sense of style. We also shared a couple of late-night talks on the telephone, some pleasantly random encounters on campus, and a slight fear of our Literary Criticism professor.

I won’t go into other details here (that’s the ‘You Must Love Me‘ story, and the iPod hasn’t shuffled that way yet), but after a few weeks of flirting, one flat semi-date, and a risky letter laying it all on the line, he was not as enthralled with me as I was with him. And as my pathology has historically shown, it’s the ones who want nothing to do with me that I seem to love the most.

I had to let it happen,

I had to change…

And so, long story short, he broke my heart, in the kindest possible way, but a broken heart is a broken heart and there’s nothing much to be done about it. That November the ‘Evita’ soundtrack was released. It was Madonna in an Andrew Lloyd Webber musical – a gay man’s dream – but while the rest of the Madonna-mad homos celebrated, I tried to heal.

Back in those days, I lived a very organized and regimented life. Chalk it up to my Virgo birth sign, or my parents’ rigid structure – the point was, I had my school life and job and creative outlets strictly planned out, and there was little to no time for an emotional breakdown or messy feelings to muck up the flow. But I had read somewhere that Madonna claimed she allowed herself one day to get over a bad break-up, so the Tuesday that the ‘Evita’ soundtrack came out I designated as that get-over-it day.

Luckily, I did not have classes on Tuesday, so I slept in and putzed around the condo a bit. The day was dim and overcast, but there was no rain. I walked over to Tower Records (again, this was 1996, and it still stood on the corner of Newbury then) and bought the soundtrack.

I vividly recall the press Madonna was getting at the time, especially the one-two knock-out punch of Vanity Fair and Vogue. She was poignant, vulnerable, and poised on the brink of her first comeback following the Sex years. She’d had her first child – a daughter named Lourdes – and she was healing her lifelong hurt of a lost mother and a number of lost loves. In my dismal state I could somehow relate, and suddenly I wanted to be anywhere but where I was.

So I chose freedom,

Running around, trying everything new,

But nothing impressed me at all,

I never expected it to…

The next weekend my cousin’s wedding was taking place in San Diego. It was both exactly what I needed, and the last thing I wanted. A wedding is a wretched place to get over a broken heart, but at our darkest moments most of us turn to family – the people who have no choice but to love us. Or so we hope.

The truth is I never left you,

All through my wild days,

My mad existence…

I kept my promise,

Don’t keep your distance.

In Logan Airport, I took off my winter coat and waited for the plane to board. In my ears I listened to Madonna sing that epic song. Midway across the country, flying over all those square states, a storm appeared to the left of the plane – lightning and thick clouds swirled, and in the dark of night I almost dared God to take all of us down – I was that far gone.

Up in the sky, I felt removed from everything. The seat next to me was empty (are there ever any empty seats anymore?) so I could lie down and nap, and the flight attendants didn’t mind. While the night progressed, I was moving West and turning back time. What could be found in those three hours I was momentarily gaining? Would there be wisdom there, and would that soothe the ache?

Landing in San Diego was a healing moment of its own – the balmy humidity was a salve on the raw coldness I brought from Boston. I hopped in a courtesy van and arrived at the hotel where my family was already going about their wedding business. All except my brother would not be told of my state of mind. I wasn’t even out yet, and the accompanying loneliness and sadness weighed secretly upon me.

I tried to distract myself with the sunniness of San Diego, and the silliness of fashion, finding a tiger-print coat and a maroon ostrich boa in a vintage shop. I asked my brother to take a photo of me walking in a park, head down and countenance downtrodden, and it would become that year’s somber Christmas card. Through it all, I couldn’t shake the feeling of being unloved, and while my head (and my own brother) was telling me that this person was not worth the trouble, my heart would not be quieted – the heart wants what it wants.

At the wedding I talked and laughed with family. There were compliments on my outfits – there would always be compliments on my outfits – and if I had nothing else, I could still look good. I wondered then, if that’s all I had to offer. My lost suitor had been captivated by my clothes – in fact our first conversations revolved around clothing. How could such a superficial thing even compare to what I was feeling on the inside? And what do you do when you’ve built up such a pretty facade, but all anyone wants to do is look?

Such silly ruminations, and such a silly boy I was for feeling so devastated. Perhaps it’s even silly to speak of such things now. Yet these are the things that shaped me into the man I am today, and in so many ways those faults have not been perfectly patched. They run deep, and they run wide, and no matter how far I think I can go, they’re always with me.

And as for fortune and as for fame,

I never invited them in,

Though it seemed to the world

They were all I desired.

They are illusions,

They’re not the solutions

They promised to be

The answer was here all the time,

I love you

And hope you love me…

I didn’t cry for Argentina. I didn’t cry for Madonna and her newborn child and first shot at movie star credibility. I didn’t even cry for the boy who never sat next to me in class again.  I cried for that fact that love would never be easy for me, and that as good as I was at dressing up and making the ladies laugh, I could never be good at love.

In one of the magazine articles of the time, Madonna was talking about how she gained the coveted title role of the movie, and she said something that I grasped as hopeful for my goal of attaining a guy:

“I thought of a line from ‘The Alchemist’ that goes something like, “If you want something bad enough the whole earth conspires to help you get it.””

That’s not true in matters of love, and I think Madonna knows that too.

Have I said too much?

There’s nothing more I can think of to say to you…

But all you have to do is look at me

To know that every word is true.

Song #17: ‘Don’t Cry For Me Argentina’ – November/December 1996

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