Waiter Confidential: What I've Paid to Play

The time we spend in this business can be a gamble. From the easy money to the nightlife and liquor-fueled libidos, there's a risk we run of getting addicted to the action.

I'm the perfect example: That not-so-lucky winner you hear stories about. And the tale of my $4,000 tip, I suppose, will sum things up nicely.

When my ex-wife and I got engaged, I bought her the ring a waiter could afford, rather than the one she deserved. Along with loving, honoring, and cherishing her for a lifetime, buying her a bigger, better diamond one day was one of the things I vowed to do as her husband.

Shamefully, it was one of the very few promises I kept. Over the course of our years together, I gave in to the dark side of this business: Too many late nights out after work, partying like I didn't have a wife and two kids waiting for me at home.

So, when that once-in-a-lifetime windfall came my way and a very well-to-do regular of mine crammed forty C-notes in my pocket as a Christmas tip, I tried to buy forgiveness from the girl I'd gone on to disappoint in so many ways. I called home excited, assuring her I was about to make good on something she'd been without for too long.

"Please, just promise me you'll come straight home after work," she pleaded, as if she hadn't even heard my great news. "Don't stay out tonight, please."

A week or so later, I parlayed my monster tip, a little more cash, and the trade-in value of my wife's original engagement ring into a near-perfect, two-carat solitaire, procured for me by another good bar customer in the jewelry business from a private seller.

I was so proud of myself. And for a time, the new bauble seemed to content my wife, too.

But aside from the size of the rock on her finger, nothing else ever changed for the better in our marriage, no thanks to me.

Less than two years later, we were divorced. Not many months afterward, the mother of my children fell in love with someone else, and sold the ring to help furnish the home she still shares with a far better husband.

On the bright side, my ex has since found it in her heart to forgive me for what I've done, and we've emerged from mutual heartache as the best of friends. Now, I visit her and the kids almost daily, dropping off my tip money for support.

And whenever I'm there, in that house where everyone in my family but me now lives, I consider all the games I've played in this business. And the cost.

Anonymous has seen it all in 25 years of waiting tables and tending bar at some of the Valley's most beloved restaurants.