I will second Square One. Make sure you get some of their jams.
Bottega Louie is loud, expensive, and mediocre. This is a place to take your parents. It's the kind of restaurant you'd find in the theater district in New York.
Gay night: Akbar on a Friday, Fubar on a Thursday if you want some raunch. MJs is sad, avoid, avoid. There is also a Mexican restaurant a few doors down from Akbar, called Malo, that has so-so food (except for a few excellent stand out items) but great ambiance and great cocktails. A fun place to get drinks and a bite to eat before a night out. Also, if you're in Silver Lake and craving some of the best pizza around, check out Hard Times Pizza.
Breakfasts and brunches: lots of options. Really, the one place that gets "wows" from every visitor I take there, is The Griddle. If you like over the top pancakes, it's great. Toast is TERRIBLE. It has always been mediocre, but it was featured on The Hills so it's now terrible and crowded.
Church and State is okay... very expensive and can disappoint. If you are going to dine downtown, I would recommend other places first. Bar & Kitchen. The Varnish for cocktails. If you want a dinner in Hollywood and don't mind throwing some money around, I'd recommend Fig & Olive or Comme Ca. Comme Ca has a divine cheese selection and upper tier cocktails. It's no obscure little restaurant but it delivers.
Coolhaus ice cream is very special. Look for their truck, or check out their storefront in Culver City. The Oaks Gourmet in Hollywood / Los Feliz adjacent has *excellent* food. Expensive. But the grilled cheese night on Wednesday is unforgettable and the breakfast menu every day is top tier.
I am sorry you are staying in Santa Monica. Santa Monica is the heart of LA's upper middle class stroller set. I hate the food around there. Anything good is too expensive. Get away from Santa Monica as much as you can. The best places to dine and explore are, in this order: Downtown, Hollywood, Silverlake, Los Feliz.
Fun doses of pretension: a cocktail at the pool at The Standard West Hollywood, if it's open in January. Skip the bar at the Hotel Bel Air, it's awful now. A drink at the Sunset Tower bar, some of the best low key star watching in LA. And really, a gem in LA that must never be skipped: the Beverly Hills Hotel. A landmark. A legend. Have brunch at the Polo Lounge or lunch and cocktails at the pool. A unique place. You must see it.
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