First dates
Bowling and mac and cheese
Distract yourselves from awkward conversation with a round of pins (after 8pm $7; shoe rental $3) at retro alley The Gutter (200 North 14th St between Berry St and Wythe Ave, Williamsburg, Brooklyn; 718-387-3585, thegutterbrooklyn.com). Also helping your game (if not the game): local beers, including Brooklyn Winter Ale ($6), Chelsea Checker Cab ($4) and Six Point Brownstone ($6). Once you've bowled that 89, amble over to butcher-shop-turned-eatery Peter's Since 1969 (168 Bedford Ave between North 7th and 8th Sts, Williamsburg, Brooklyn; 718-388-2811, peterssince.com). Split the signature rotisserie chicken (half $10.95) and share three comfort-food sides ($9.95) like macaroni and cheese, mashed potatoes and corn. By that point you'll be feeding each other.
Hot tapas and sensual jazz
Cozy up with a bottle of wine and some small plates (save the pigging out for when you're married, year two) at the petite Snack Taverna (63 Bedford St at Morton St; 212-929-3499, snackny.com). After sharing the shrimp Santorini ($13) and wild mushroom yiouvetsi casserole with orzo and sheep's-milk cheese ($11), walk to the Jazz Gallery (290 Hudson St at Spring St; 212-242-1063, jazzgallery.org). The nonprofit cultural center showcases up-and-coming professional musicians and has a rotating exhibit of jazz-themed artwork. Don't play yourself—it's best to make reservations here. Tickets for most shows start at $10.
Relationship dates
Burlesque and Basque food
Date night with your old familiar plus-one is an evening of Netflix Watch Instantly. Pep things up with raunchy humor and pasties at the Slipper Room (167 Orchard St at Stanton St; 212-253-7246, slipperroom.com). Burlesque shows, filled with crass innuendo (remember innuendo?) and outlandish costumes start at 10:30pm Wednesday through Saturday. The small stage means you won't have much of a view from the back of the bar, so get there early. Keep the piquancy up with a spicy Basque dinner and live flamenco, Cuban salsa, bossa nova, tango and Latin pop music at Oliva (161 E Houston St at Allen St; 212-228-4143, olivanyc.com). The red or white sangria (pitcher $19) should go straight to your head.
Mini food tour and a midnight movie
You're fat and happy these days; the least you can do is walk in between eating sessions. Start your mini food tour at Nolita classic Cafe Gitane (242 Mott St at Prince St, 212-334-9552) for French-Moroccan staples like spicy Moroccan olives and oranges ($6) and couscous with red peppers, raisins, toasted pine nuts, hummus and eggplant ($11.50). Then meander over to Michael Huynh's latest, Vietnamese beer garden Bia Garden (154 Orchard St at Stanton St, 212-780-0010). Throw back a few Asian ales and devour a spicy green-mango salad ($9) and a plate of crab spring rolls ($7) before topping off your wandering meal at The Stanton Social (99 Stanton St at Ludlow St; 212-995-0099, thestantonsocial.com). Standouts among the bevy of international tapas include French-onion soup dumplings ($12) and red-snapper tacos ($10). On Friday and Saturday nights, catch a midnight movie at Landmark Sunshine Cinemas (143 E Houston St between First and Second Aves; 212-330-8182, landmarktheatres.com). Tip: Skip the popcorn.
Anniversary dates
Pottery and a stellar show
Extend the celebration with a class series at Mugi Studio (993 Amsterdam Ave between 108th and 109th St; 212-866-6202, mugipottery.com; $266)—how else will you ever re-create that scene from Ghost? Then give yourselves a reason to hold hands again with some stargazing at the Hayden Planetarium (enter on 79th St, 212-769-5100, haydenplanetarium.org). Catch Journey to the Stars, the Whoopi Goldberg--narrated film about the history—and future—of the luminous orbs, spanning billions of years ($24, which includes museum admission; it screens every 30 minutes daily). Kind of makes your relationship feel less ancient in the scheme of things.
A couple's massages and a relaxing meal
If you're feeling sore after jujitsu, bowling and skating, try a massage—together, at Juvenex Spa (25 W 32nd St between Fifth and Sixth Aves, fifth floor; 646-733-1330, juvenexspa.com; $395 per couple for 150 minutes). Stay Zen on the way to Brooklyn for a prix-fixe dinner ($98) of foie gras and truffle-honeyed duck breast (among other dishes) at the River Caf (1 Water St at Old Fulton St, Dumbo, Brooklyn; 718-522-5200, rivercafe.com). If you don't want the night—or the view—to be over, take a stroll along the Promenade. Manhattan looks so peaceful from across the river.
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Dates for everyone
The best dates for every personality and mood.