There is one place in the city that will seal the deal for you: The Tower Bar at the Sunset Tower Hotel.
The food is good (I recommend the steak salad or the halibut), the staff is incredibly attentive, the lighting is dark, and the decor is Donald Draper swank.
I go here every year for my birthday: I've never had a terrible meal and I've always had an amazing time. It's one of those places I wish I could just hang out at every evening, get to know the bartender, and order a scotch on the rocks (I don't even like scotch - it smells like my grandfather and tastes like Chloraseptic - but it seems 'cool' and makes me feel important when I drink it). Unfortunately, unless I meet a sugar daddy at the bar (sorry Mike) I'm not going to be adopting this lifestyle anytime soon...
The other thing that makes me feel important when I come here is that its always filled with celebs brokering deals on their next big movie. Last time we were there we sat next to Quentin Tarantino and Michael C. Hall (+ awkward wife). However, if you've got one of those significant others who is obnoxiously obsessed with celebrities spottings and feels compelled every time they see one to say hello and make 'buddies' - dont bring them. That is not a swank thing to do. Bring your goo-mah instead.
I'm not sure what their Valentine's Day menu is like this year but, like most restaurants in LA, I'm sure its ridiculously over priced. I'd recommend going here Feb 12th, 13th, or 15th instead (or for any other celebratory occasion OTHER than Cupid's favorite day to rip couples off.)
Remeber: the place is in a hotel, so if you're feeling REALLY confident - maybe book a room too? The rooms are swank (word of the day) and they've got a great pool off the Terrace Bar with a view of the city.
Sunset Tower Hotel
8358 Sunset Boulevard
West Hollywood, CA 90069
323.654.7100
Good Luck and Enjoy!!!
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