Best Wine Bar for an Intimate Date Night

O'Hara & Flynn Wine Bar

Staff Pick

O'Hara & Flynn is tiny — like, four-tables-and-a-bar kind of tiny. Add in a musical guest in the corner, and the place gets downright cozy in a hurry. But with a friendly, knowledgeable staff and a bohemian ambience, you'll feel right at home before long. Another thing we like about O'Hara & Flynn: The musical performers aren't just any old schmoes off the street. On various nights, we've seen local luminaries Bill Carson, Leah Suarez, Steven Fiore, and Nick Jenkins posted up in the corner, serenading the tiny crowd for hours with gentle originals and cover songs. Order a glass of wine and a plate of cheese, sidle up to your date, and don't forget to tip the performer. Perfecto.
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