31 Days of Rest & Risk :: Day 26 ~ Playboy

The Last Freaky Friday
I’m published… but not how you might think.

On October 26, 1991, (21 years ago), my good friend Lara Oliver asked me to escort her to her Debutante Ball in the Trump Plaza in New York City. My best friend Tim Webster was dating Lara at the time, but she needed two escorts, so she asked me.

It was a risk.

* Thousands of people from many countries would be attending this event.
* I’d have to wear a black tuxedo and white gloves.
* I’d have to learn how to waltz.
* I’d have to waltz with Lara in front of “the world”.

This was before Dancing With The Stars was popular. Waltzing was not something 23 year old guys were doing for fun… at least not me.

They say what happens in Vegas… stays in Vegas…
but evidently what happens in New York… gets published in Playboy!

All the details of how a photograph of me, Tim, a couple other escorts, and a Debutante, got published for the feature article for Playboy in March of 1992, aren’t important for this post… Maybe for another time… and please don’t go check to see if I’m telling the truth…
just trust me 🙂

Being published in Playboy was something I was embarrassed about for 19 years…
but now it’s a memory I cherish… because…

… my friend, Lara Oliver Webster died on February 5, 2010 of a brain tumor.
She was 39. Mother of 3 kids. Married to my best friend for 15 years.

Lara’s funeral was amazing! Over 1500 people, from around the United States attended her celebration. She was an amazing person. Caroline spoke at the funeral as her close friend… another honor we accepted… that has lasting memories. If you have 5 minutes… here is a video put together by Mike Eller of her celebration service.
(If you can’t watch it below, just click here to go right to the vimeo site)

Lara was and is a Christian. She is now “home” with Jesus. We will see her again…
and when we do, I’m sure we will reminisce a little about that ridiculous weekend in NYC.

Because I took a risk, and escorted Lara to her Debutante Ball in 1991…
I had the honor of waltzing with Lara Oliver Webster…
at The Trump Plaza…
in New York City…
in front of the world.

It’s a ridiculously good memory I have with Lara that reminds me of what’s really important in life.

~ Greg

{This is a series of posts for 31 Days of Rest & Risk. To read the other posts, click here.}