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If you have zero gut feelings about whether this date is going to be surprisingly great or predictably horrible, take them to The Mayflower in Clinton Hill. It’s hidden behind some thick vines with almost no signage, and the dim vibe inside helps maintain the feeling that no one you know will ever find you here. The cocktails also happen to be excellent, and if the date is going well and you think you have enough conversation topics to sustain you through dinner, you’re steps away from Aita, the charming neighborhood Italian spot next door.
In any season other than winter, drinks at Mayflower after a dinner at Aita would seem like a lazy move. But if it’s anywhere south of 40 degrees outside, your date will appreciate the fact this cocktail bar is just next door. It’s also from the same owners, and it’s similarly quaint in an antique-store kind of way.