Skate date
Get things rolling with the aid of Uptown Skate School (646.462.3929, uptownskateschool.com; two people $100, if you mention TONY $65), whose instructors will come to the location of your choice for a one-hour, semiprivate skate- or longboard lesson. At Hudson River Park’s Skate Park (30th St at the Hudson River, hudsonriverpark.org; daily 11am–7pm), you can practice what you’ve learned on the bowl, street course and mini half-pipe for free—you just need to sign your life away in a waiver. (How romantic!) Afterward, take some of the edge off with $2 cans of Schlitz and PBR at badass dive Blue Ruin (538 Ninth Ave between 39th and 40th Sts, no phone), where shots like the Cherry Bomb are served aflame.

Rock climbing and relaxing
Relationships are filled with ups and downs, so get yours started on the right foot scaling the 30-foot indoor rock-climbing wall at The Rock Health & Fitness Club (22-15 31st St at Ditmars Blvd, Astoria, Queens; 718-204-1400, therockhealthandfitness.com; day pass $20 per person, includes equipment). And if things don’t work out, well, that’s what the helmet is for. After you’ve reached the summit and back, stroll on terra firma to Himalaya Teahouse (33-17 31st Ave at 33rd St, Astoria, Queens; 718-777-7450, himalayateahouse.com), which has less to do with Mount Everest than with Zen. Order a large pot of organic rooibos tea ($5.95) and Tibetan steamed momo dumplings ($8.95) to share with your little dumpling while you chill.

On the water
If you’re looking to impress your date with something new and unexpected, perhaps an activity on the water with skyline views, then we’ve got two words for you: kayak polo. With a small boat as your trusty steed, join members of New York Kayak Polo (Pier 66, 26th St at the Hudson River; nykayakpolo.org) for an intro session on the last Tuesday of the month at 6:30pm. Games that day are open to anyone—and boats, paddles, life vests and helmets are provided at no cost (first-timers just need to pay a $5 insurance fee). Stick with the boat-in-the-water theme and head to Pier 66 Maritime (Pier 66, West Side Hwy at 26th St; 212-989-6363, pier66maritime.com), a former railroad barge–turned-bar, for white sangria ($8) or a Blue Moon ($6) on the roof deck. Since the most exotic marine life you’ll see floating in the Hudson is cigarette butts, get your fill of the real deal at Bongo (299 Tenth Ave between 27th and 28th; 212-947-3654, ongonyc.com) and suck down a half-dozen oysters ($18) from its extensive selection.