Finding My Jeffrey: Summer Date Ideas

Dating in the Northeast is so much more fun when it’s warmer out during the summer months. Today will be a NYC-centric post – I’m sharing my favorite summer date ideas in and around the city.

I know I had promised this post awhile ago – things have been crazy busy, but it’s finally here.

Picnic in the Park

One of my favorite things to do in the summer, whether it’s with a date or just with friends, is to picnic in Central Park or elsewhere. Pack towels, a basket full of goodies, and several cans of Sagaponack-based Wolffer Vineyards’ rose cider and you’ll definitely have a fun time. I enjoy making the trek from Brooklyn to Central Park. Nothing says summer in NYC to me like a day in Central Park.

Funny story – I remember having a second date picnic in the park one summer; however, it was near dusk, and we were told we needed to leave the park. We didn’t move that quickly and when we finally got to it, we could not find an open entrance. We ended up having to jump a fence. I’m 5’1 so this was quite a difficult feat. The skirt of my summer dress ended up getting caught on the fence as I was just about over. Suffice it to say, my date saw more of me than I expected on a second meeting.

The Whitney Museum and Walk on the Highline

While museum dates can sometimes be awkward – especially if it’s a first date and there’s some particularly weird art around, I think the “new” Whitney Museum of American Art in Manhattan’s Meatpacking District is a wonderful summer date idea. The museum is open late on Fridays and Saturdays, so it’s great if you work later hours. However, I think the best time to go is around the time the sun is setting. The Whitney has tons of outdoor balconies with fantastic views of the city. It’s particularly stunning to see the sunset reflected on all of the modern buildings in the area. After, you can take a stroll on the Highline which is usually filled with different vendors during the summer (think wine, ice cream, and other treats). If you’d like to have dinner in the area, I recommend farm-to-table restaurant, Cookshop; or if you want to be fancy, Del Posto (you should probably have a reservation though).

Drinks, Conversation, and People Watching

This one may be standard, but it’s my favorite one on the list. I love spending a hot summer evening having drinks, people watching, and chatting all night. Here are three of my favorite places:

Weather Up (Brooklyn location): I was first introduced to Weather Up when I lived in downtown Manhattan and visited their Tribeca location (which is also great). When I moved to Brooklyn, I was happy to learn they have another location pretty close to my new apartment. What’s more, they have outdoor space in the back. Their cocktails are also fantastic. It’s so much fun to grab a cocktail and sit outside in their backyard. By the way, I find that New Yorkers are obsessed with outdoor space – probably because it’s hard to come by for ourselves in the city. Another plus – this place never gets too loud so it’s perfect for conversation.

Maison Premiere: This Williamsburg spot is known for its New Orleans cuisine and has been on a number of “best” lists. I like getting oysters and a cocktail.

Terroir: If you love wine, you have to visit Terroir in Tribeca. I find whenever I go here, the staff makes wine very approachable and they’re always happy to give recommendations. I learned here that boxed wine isn’t always terrible (they usually have one on the happy hour special menu during the week). Their Italian-leaning snacks are also great. I love this place as a date spot because it’s casual, but still nice.

Dia:Beacon

If you’re looking to escape the city for a bit, but not travel too far. A trip to Beacon, NY is a fun, little romantic getaway which can easily be done as a day trip. It takes a little over 2 hours on public transit to get there depending where you’re coming from (you can also drive and get there in less time). Beacon, NY is a quaint, artsy town in the Hudson Valley which is known for cute little shops and restaurants and mainly for the Dia:Beacon art museum which houses modern and contemporary works from among others Dan Flavin and Gerhard Richter. When I visited a few summers ago, I also had a leisurely lunch at the restaurant at the Roundhouse Hotel which overlooks a small waterfall. It was the perfect afternoon and little escape from the grind (and oppressive heat) of city life.

You could also extend this trip over a long weekend and perhaps squeeze in some other spots in the Hudson Valley. Some suggestions include the Storm King Art Center which is known for its outdoor art installations or a visit to Blue Hill at Stone Barns in Tarrytown (which is still on my bucket list). If you’re planning to do this, I would recommend renting a car.

What’s your favorite date spot in your respective cities? I’d love to know.

By the way, if you’ve missed the first two posts in the Finding My Jeffrey lifestyle series, be sure to check them out here and here.

Also find me on Instagram @mannersandmanhattans #livewellmodernly