I don’t have many problems in life. Missing my train and being forced to take the 4:54 AM home to Long Island after a night of boozing tops the list for me. If I could give the gift of an extreme makeover experience; especially during the holiday season, “big-ups” to me. I had a rare and special opportunity to give an older gent named Donnie a shot at youth again.
Bob; a trusted friend and valued business resource, referred me to his client Donnie. Don had done a fair amount of business with Bob’s firm and this evening I was to make sure that he was a happy camper.
Bob explained the details of the driving / transportation gig that required my services. I was expected to “engage the client in light-hearted conversation” and “take charge of him when necessary”.
I kindly accepted the offer; but seriously, what was I getting myself into?
Bob further explained that Donnie hasn’t been on a date since the 1970’s nor has gone to New York City in over 20 years. Bob wanted to do something special for Don over the holidays, so he convinced him to get an extreme makeover in preparation for the big night.
Donnie tried on new outfits and agreed to let a stylist work with him. (Requesting: The “Steven Segal” look.) Getting a commitment from Don to take a female companion was more difficult. Bob’s persistence ensured the potential backseat magic to happen later that night.
Itinerary for the evening included:
Picking up Donnie and a date at his house, driving them to Manhattan for the Radio City Christmas Spectacular, and then driving them both home.
We anxiously waited for the mystery date to arrive. After 20 minutes of waiting, Leah made her grand entrance barreling her 1989 Chrysler LeBaron down the street and swooping into the driveway like the pizza delivery guy in Home Alone.
I was pleasantly surprised with the quality of Donnie’s date. Leah definitely had the MILF vibe going on. She was a flirtatious bar-maid who made Donnie feel special. She had no problem with him putting an arm around her in the backseat. Of course Don crossed the boundary line a few times, but Christ this was his first date in over thirty years!
They both enjoyed the Christmas Spectacular courtesy of Bob. On the ride home Donald invited Leah back to his place for drinks. He told her he had a bottle of champagne with “her name on it”. She respectfully declined, but I admired him for having the balls to ask.
Donnie had his “mack on” with his arm around her. As the hired chaperon, I still looked in the rear view for any petting over the pants.
Bob’s client was appreciative of my services that evening. I don’t think he realized I ended up getting Leah’s number after he left. What up Ma?
Don is lucky to have Bob (the estate planner) looking out for him, and in this case find him some fresh tail among high-yield and dividend paying investments!
Tags: deserve, donnie, donnie darko, especially, extreme makeover, films, gifts, holiday, holiday season, incest in fiction, new york city, real santa, santa, the gift
