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Casual & Quiet - Dessert and Drinks in the District

I've walked by Circa before and glanced at the menu. That could be an intriguing place.

The Tabard Inn sounds good - though I'm worried it could be a little too upscale. Would jeans and sweaters fit in there?

Casual & Quiet - Dessert and Drinks in the District

I'm looking for some place comfy, casual, and quiet to take my wife and a few people for dessert and drinks on her birthday. We're doing Komi the night before, so we don't need anything terribly fancy. Just ok desserts and decently priced alcohol. Could either be a bar somewhere - or the bar of a restaurant.

I was thinking somewhere along the lines of C. Park, Woodley, Dupont.

Thoughts I've had -
Brickskeller - Except they have no dessert and they never seem to have the beer I want.
Open City - Not terribly comfortable, but could fit the bill for dessert and drinks. I've only been there for brunch.

Neither of these really excites me though. Any suggestions?

Thanks in advance,