Dog Day Afternoon (AKA The Dog Lover’s Date)

For an outdoorsy (but not too strenuous) first date, meet at the Brooklyn Public Library to pick up some coffee and pie from Four & Twenty Blackbirds. Take it to go and stroll through Prospect Park’s Long Meadow towards the dog beach (a roped off lake by the baseball fields). Enjoy your pie with a front row seat to pure canine happiness.

Hands-On Evening Date

If an evening of awkward get-to-know-you conversation fills you with dread, book your first date at a Brooklyn Brainery class. Brainery offers short classes in any and every field for very affordable prices, many of which happen during after-work hours. Pick something hands-on—like dumpling-making—that allows for a bit of chit-chat and/or collaboration. If you hit it off, head next door to Gold Star Beer Counter for a pint––or to Blue Marble if ice cream is more your thing.

The Impressive Quickie

If you like things short, snappy and ultra-cool, take your date to Prospect Height’s own speakeasy, Weather Up. Inside the unmarked white tile building hides a lush barroom with some spectacular cocktails. If you want to extend the evening, head down the block to continue the conversation at Chuko Ramen.

Last Minute Drink (AKA The Dive Bar Date)

When you need a spot in a hurry, tell your date to meet you at Soda Bar. This dependable dive bar has plenty of dark corners and sticky tables for getting to know each other––and provides great people watching.

Bar-to-Table (AKA The Dinner Date)

Take a tip from Aziz Ansari and meet your date for a drink at the Four Horsemen in Williamsburg. Enjoy a glass or two at the bar while you wait for your table. The shareable plates are perfect for date night, and delicious to boot. If the night is going really well, finish it off at Westlight for a sparkling skyline view.