If Peter Gibbons was real, he'd definitely say to hell with Flingers and Chotchkie's, and have Jennifer Aniston meet him at Bar Louie: a lounge-like tavern in Midtown in which everything seems just overdone enough, from the massive circular bar, to oversized tables, giant flatscreens, and more food and drink than is currently being withheld from Milton
Said menu is very, very healthy: mozz/parm-stuffed meatballs, onion ring-topped bacon cheeseburger sliders, drunken fish & chips that will fit in pretty well, and jalapeno/bacon-baked mac, plus sandos like the Luigi (shaved ribeye & cheddar, and bizarrely no mushrooms that make you taller), shrimp po' boys, and 10 burgers like one loaded with guac and pepper jack
To keep that fish & chips lubricated, there're 20+ beers including rotating seasonals, margs & mojitos, and cocktails like The Ultimate Bloody Louie (a Mary w/ Guinness), and a roster of martinis including the Tickled Pink, which's what Lumbergh did NOT do to Aniston. Not that Lumbergh at least.
Tuna Eyeball with Timothy DeLaGhetto and Ben Sinclair