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George Clooney pulls up on a motorcycle and doffs his helmet with casual grace.   He is arrestingly handsome in person, and his suave, familiar smile leaves me breathless.  But looking into his warm brown eyes up close, I see a tinge of sadness.  The unlucky-in-love Clooney is said to be in mourning these days; recovering from yet another failed relationship.

“I’m sorry I’m late,” George says, holding the door for me as we enter a small, unpretentious Hollywood café.  “I just got back from playing racquetball with Brad [Pitt], and things got pretty heated.  We do enjoy a little competition.”

Off the racquetball court, it can be argued that Brad Pitt is the one coming in ahead these days.  With a beautiful woman on his arm and an enviable family life, Pitt has been lucky enough to find that special someone.  He never has to worry about having no one to come home to at night.  Though Clooney has dated a string of beautiful women over the years, it’s widely evident that he still has yet to find a soul mate.

George orders his coffee black and I do the same.  “I’m trying to watch my figure,” he says with gruff charm, and winks.  It’s obvious that Clooney is concerned about maintaining his attractiveness.  As a single man in his forties, he is well aware of his diminishing appeal.  The older he gets, the slimmer his chances are of ever finding a woman to settle down with.  These are sobering thoughts for a single man of a certain age.

I decide to be daring, and address the elephant in the room, asking Clooney point blank about his most recent devastating break-up, with Vegas cocktail waitress Sarah Larson.

“Wait, who?” he says, expertly feigning confusion.  It’s clear that his heartbreak has not yet run its course.  “Oh right, Sarah.  She’s a great girl—it’s too bad it didn’t work out.  I wish her the best.  Let me tell you about this project I’m working on with Don Cheadle.  The man is a fucking genius.  It’s been so much fun kicking ideas around with him.  The other day we were out in LA…”

As Clooney talks, I am struck by how much he reminds me of a lost little boy.  I want to take him home with me and set him up on a blind date with my maiden aunt.  His rumpled button-down Oxford shirt and salt-and-pepper hair cry out for a wife’s loving, critical attentions.  Still, I admire the carefree smile he presents bravely to the world, hiding his pain and loneliness with a life full of exotic travel, wild parties and a rewarding, illustrious career in film and television.

I halt my mournful reverie long enough to notice that Clooney is telling an amusing story about the time he and Matt Damon lost a friend’s Camaro in a poker game in Mexico.  “Man, I shouldn’t be telling you this,” he cackles gleefully.  “I could get in trouble.”  I wonder briefly what his apartment looks like, and the thought makes me sad.  No matter how he tries to fill it with track lighting and stylish décor, underneath the expensive rugs and modern furniture it must be a barren place; an empty, husk of a shrine to his failed hopes and dreams of becoming a happily married man.

As our conversation winds down, George pays our tab and escorts me to my car like a true gentleman.  It is heartening to realize that such men still exist in our world, even suffering as they do from lonely hearts.

“Don’t ever give up hope, George,” I want to tell him.  “I know in my soul that there is a woman out there for you.  A partner in crime; someone for you to wake up next to every morning for the rest of your life, instead of a steady stream of cocktail waitresses and young party girls who are only out for a meaningless fling.”

But instead, I only smile as we part ways.  “Keep your chin up, kid.” Clooney tells me.  “It’s nice to see you smiling.”  A stretch limo pulls up to the curb next to him and the back window rolls down.  Through peals of laughter I hear a female voice inviting him to climb in.  As the limo pulls away, I catch a last glimpse of Clooney.  He has a glass of champagne in one hand and a woman’s stocking in his teeth.  Perhaps this time, he will finally find love.

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