Melisse is lovely, but in this instance, it's comparatively cheap. Besides, I can't see Chef Citrin going off his own menu to make an over-the-top steakhouse type of meal, which is what Mr. Calacanis seems to prefer.
(Both gentlemen are named Jason, so for clarity, I'll use their surnames.)

I'm suggesting Mr. Calacanis have Mr. Nazar rent out a mansion in Bel Air, Malibu or perhaps Hollywood Hills, and have a private chef at his beck-and-call, to make whatever his (Mr. Calacanis') heart desires.

He could start with seared foie gras with a port wine reduction, or a flight of caviar with all the trimmings. Both of these would be matched to a sparkling wine, but instead of heavy yeasty French champagnes, I suggest crisp and sparkling Cava.

Next I'd propose a traditional steakhouse iceberg wedge, with a dressing made of genuine Roquefort purchased from the The Cheese Store of Beverly Hills. Another choice would be a nice Caprese salad, and of course, I'd bring an assortment of heirloom tomatoes I raised myself.

This could be followed by a Lobster Mac & Cheese course, or if they'd like to go lighter, oysters mignonette: they can't get fresher shellfish that what's shucked before their very eyes.

Or they could have both. :-)

Then I'd propose a totally over the top entrée, such as a trio of filet mignon, a rare tenderloin of venison, and bison braised in red wine , served with truffled French fries. (Vegetables? We don't need no stinkin' vegetables... but I'd happily offer the best of my harvest from my half-acre garden if only as a garnish.)

Dessert could be home-made Tahitian vanilla ice cream served aside warm flourless chocolate cake pulled straight from the oven.

These are merely suggestion, of course; I've just got the impression that Mr. Calacanis prefers 'real' food instead of something like "hearts of palm stuffed five ways" or "essence of deviled quails egg over tomato aspic" or whatever it is that's being served by avant-garde restaurant of your choice.

Naturally, wines would be paired as well, and they wouldn't be limited to Melisse's wine list.

Hey, Jason, you hungry yet?

I'll also act as your personal sommelier for the evening, checking the wiines for faults (generally, 1 out of 5 wines is "corked"), serving tableside and answering any questions.

I should also mention that the selection of wine is key here. Many of the most statusy, popular, premium cult wines are NOT food wines. They can cause a trainwreck in the mouth when paired with food, overpower a dish, shock your palate or merely clash with your courses.

Ideally, as with Chef Joanna's suggested menu, the list of wines for this decadent meal should match and enhance each course and each wine, like each course of food, should progress. Many people understand how to pair food with wine but not how to plan a progressive wine list for a multi-course dinner. Sommeliers understand both and work closely with chefs on these special events.