The Gold Coast hideaway is about indulgence. But looking over your shoulder in an open dining room has a way of keeping your id in check. So do what the high rollers do: arrange to enter through the loading dock on the side. It's indoor, so it's bright and clean and leads directly to a restaurant's private dining room, where you can be as uninhibited as you see fit.
Get Your Affairs in Order
This whole drama about Bachelorette "winner" Chicagoan Ed Swiderski (allegedly) stepping out on his newly affianced TV soul mate, has left you shaken. But let us reassure you: you can easily keep your affairs out of the tabloids, so long as you frequent the city's most discreet locales. Let us show you where.
Sure, it's sexy, but you wouldn't dream of elbowing your way through the weekend bottle service crowds that fill the upper deck cabanas here when you need a little one-on-one time. However, this Bucktown-by-way-of-Miami cove makes an excellent midweek rendezvous point for a martini, a glass of wine, maybe a Waldorf salad, just a little calamari…who knows where it will lead. Especially because those cabana drapes can be pulled shut.
Sometimes you want to be extravagant, but without being hey-look-at-us-we-just-ordered-the-20-plus-course-kaiseki-tasting-menu extravagant. For those occasions, L2O has re-created an intimate Japanese two-person tatami room, completely enclosed, filled with grass mats, kneeling servers and a cedar table that's sanded down after every meal. Just in case someone dusts for prints after you leave.
This former Paramount Pictures warehouse, now a sexy bordello-red Jerry Kleiner spectacle, isn't the most subtle place for an affair. But quickly make your way past the cacophonous colors of the dining room to where former film vaults serve as semi-private nooks for you and the night's leading lady—or her understudy. You can request one when you make reservations, though they're not guaranteed. But you're a big believer in happy endings.
Hand it to Italian Prime Minister Silvio Berlusconi, whose handling of adultery allegations make Bill Clinton, Eliot Spitzer and Mark Sanford look like schoolboys. But the Italians have always had a certain flair for keeping things low-key. For instance, check out this stunningly old-school Irving Park spot with four secluded booths, giving you plenty of privacy should find yourself twirling someone else's spaghetti.