How to live like an Upper East Side playboy? Manhattanite Serena Shahidi knows. She takes Staten Island native Sebastian Conelli on a tour of the classiest places to eat, drink and even smoke in the UES. At the Carnegie Club, it’s still legal to light up indoors, despite the city banning smoking in bars in 2003 during the Bloomberg years. It’s no wonder the cigar club is one of Shahidi’s favorite spots to act our her “Bond girl fantasy.”

The wine-and-dine duo also hit up the Lexington Candy Shop, a lunch counter dating back to 1925, for old-fashioned Coca-Cola floats, Serena’s Wine Bar — no relation — and the Carriage House for tea and cucumber sandwiches. Their last stop is The Auction House, a dimly lit date-friendly bar with no sign out front, where they sipped a cocktail called the Smokin’ Honey mixing bourbon and mezcal.