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I have used the outdoor tables at Michael's for more than one special occasion dinner and that place came through every time. Now, I will introduce the caveat that I did this when Sang Yoon was in the kitchen (Father's Office now) and David Rosoff (Mozza now) was the GM. When Michael's was serving flower salads for $8 in 1988 it was definately trendy, but these days I would just consider it one of deans of dining Santa Monica dining.
I just had dinner at Chinios on Wednesday. Considering the decor still screams B. Lazaroff circa 1984 and I could get a table for 2 at 7:30 same day it doesn't really bend my trendy meter much. The only downside is that this is still a very expensive restaurant. Nonetheless, I loved the dinner. The deep fried whole catfish was really really good.
Stingray
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Via Veneto on Main has fantastic food, is small, very romantic. Also very expensive though.
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