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Any number of things will assure you beyond any shred of doubt (checking the menu prices, standing next to the valet parking attendant on the curb, visiting the website, walking into the palace of a restaurant) that a young lady in fitness center sweatpants and a Faith Baptist t-shirt does not, on any day of the week, under any circumstance, belong in this restaurant.

And, if that’s not enough – I’ll assure and reassure you.  This place is simply somewhere I don’t belong.  And a place I would have never imagined to visit.  But your worst fears are a dead center dart.  I disrupted all social class stereotypes and, at 11:00 at night, had cocktails and appetizers with my co-workers at this ritzy steakhouse on the Chicago River.

Cheers to every S&W employee with whom I interacted – you’d have never known I was a misfit.  Our server was cheery and professional, I learned all about her daughter’s smoking habits while I waited for my friends to return from their smoking habits.  The matre’D was delightful and accommodating, largely due to the fact that he was seating a semi-famous “regular” and his friends (among which I’m glad to be,) but nonetheless, I was surviving in style in my sweats. 

Honestly, have you ever eaten oysters in your sweats?  They were quite flavorful for such small little guys, the sauces were magnificent, and you can’t go wrong with oyster forks – cute.  There’s a first time for all new things, so don’t cross it off your bucket list, as it were.  In fact, I suggest it.  And I suggest Smith & Wollensky’s as the location for your de-virginizing.

If that kinda risk isn’t your style, then put on your Sunday (or Saturday night…depending on your lifestyle) best and take a trip to S&W.  I encourage the late-night visit, but then again, it’s all I know. 

Regardless of what I do or don’t know, I implore you to eat the Drunken Dognuts.  Apparently the “regular” crowd among us was informed and educated on the delicacy, because they were offered on the house, no questions asked.  And praise the Lord that they were!  For those of you familiar with Hoppy’s Thursday morning donuts – hear me clearly – these are no less than truly comparable!  Buttery dognut batter, crisp on the outside, warm within, covered in a powdered sugar dusting and served with three to-die-for sauces – raspberry Chambord, rum pineapple, and grand Marnier. 

Smith & Wollensky’s is a GO, certainly.  It’s out of my league, price-range, and casual attire requirement, but I’d break my own rules to go again.  I cannot divulge our total bill at this current time due to legal ramifications, however, I can tell you that on this occasion, I was treated.  And it’s a good thing, too – because too many visits to places like this and I’ll be waiting tables in my sleep.