As you read this I am on a jet plane to Puerto Rico for the weekend with a chance to change my life.

CoolGirl, whom I have been dating for close to a year now, will be there, too. And she will have the answer to the question I plan to propose.

Depending on the answer, I may come back or just stay in Puerto Rico.

That's right, my quest as a single guy dating in Miami may be about to end when I ask CoolGirl if she will stay with me the rest of my life.

Ironically, I have plenty of experience in this step. Perhaps that's why I feel like Ross from the TV show Friends. It's been just over 10 years since I asked the same question to a woman who would marry -- and later divorce -- me. And nearly 16 years since I first asked someone else, but was secretly happy we never reached the altar. (Maybe that's why this time I want to ask the question outside the borders of the Lower 48.)

Regardless, I am still nervous and questioning and wondering.

Can there be a happy ending? Did I already fill my quota of broken hearts in a lifetime? What am I going to say when I ask her?

In fact, since I decided to pop the question this weekend in the country where she was born, I feel more out of control with things than ever before.

How will I bring the ring on board the plane -- in my wallet or my carry-on bag?

What if security thinks it's as dangerous as a nail file or a large tube of toothpaste? (Don't answer that question. I know some guys who would consider an engagement ring a weapon of mass destruction.)

Having never been to Puerto Rico, where and when will I ask her the big question? Should I ask her as we clear airport security? In the back of the taxi on the way to the hotel? In the hotel lobby? On the beach? At the fort in Old San Juan?

Getting ready for this weekend involved buying a diamond ring -- I probably helped the economy with my own personal stimulus package. Fortunately, I had a trade-in (it seems I have never been at a loss for a ring -- see above). Getting rid of the old ring felt like selling a car. I hit six jewelry stores in the Boynton Beach Mall and received six quotes and appraisals.

In the end, Marks & Morgan took my trade-in and I left the final symbol of my past behind.

To get ready for this weekend, I headed to Monsieur in Coral Gables, and invited my close bud to clue him in on my upcoming change in status and ask him for some logistical advice. I would be giving up my membership in that singles club we had explored the past three years with so many pickup methods and fashions in no better city, so strategy sessions were nothing new for us.

After getting manly haircuts and tough-guy massages (it's a men's spa, for goodness sake), we met in the upstairs cigar lounge where I broke the news.

''That's awesome,'' he said, delivering a fist pump.

Here's hoping things go that smoothly on La Isla del Encanto (the Island of Enchantment).

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