Among the many dirty little secrets of Mistress Day — the day before Valentine's Day, when the unfaithful wine and dine their other lovers — one of the dirtiest may be that restaurants traditionally get an as good or bigger bump from that night than the actual holiday.
The mistress often boasts that she gets the caviar while the wife gets the fish sticks, so to speak, so it make sense that restauranteurs may actually look forward to the 13th. Philanderers have to weigh their options though so as not to run the risk of bumping into Harry from the club while getting frisky with Sally from the typing pool. This means avoiding the hotspots. You can't take your private paramour to 10 Downing, unless you have a real reckless streak (which you obviously do, so maybe that is an option after all). But Mistress Day still needs to be a lavish affair (remember the boastfulness of the other woman). It means going someplace absurdly overpriced, dark, not frequented by New Yorkers but still serving pretty good food. The Rainbow Room is always an option, but the Ciprianis might be on their way out. And it lacks romance, anyway, which is what you're after.
The prime spot for stolen moments, and Mistress Day world champion dining destination is still One If By Land on Barrow Street. It's dark and private, on a charming but hidden West Village block, a bit schlocky but still romantic in a cheesy way, expensive, has lobster, and none of your friends would be caught dead there.