The Jeffrey

For some lively al fresco drinks uptown, hit up The Jeffrey. The expansive beer-gardenish backyard serves as the perfect casual-cool summer hang and if your date is a beer nerd, they'll certainly be impressed by the selection of craft brews. You seriously can't beat the happy hour prices: $5 select drafts and cans, $2 wine on tap, and $5 well drinks until 7 pm.
The Jeffrey, 311 E 60th St.
[Photo via @bedellcellars]