A Greenwich Village Engagement Portrait

Couple in front of Caffe Reggio on MacDougal Street for a Greenwich Village engagement portrait

Looking for a fun idea for your upcoming engagement shoot?  How about re-creating your first date!  I had the pleasure of photographing Miriam and Chaim’s Greenwich Village engagement portrait on Wednesday, and they gave me quite the challenge: to document the day they started dating. In today’s blog, get all the details of their engagement portrait – from Washington Square Park to the Hudson River – and get some tips for telling your own love story.

MacDougal Street

Couple in front of tattoo shop with people walking past in a blur for a Greenwich Village engagement portrait

Miriam and Chaim are sticklers for tradition. Not only are they recreating their first date in their engagement shoot, but they are getting married on the date of their first date, October 23. Before we jump to the wedding though, let’s start on McDougal Street. It was here many years ago that Chaim and Miriam started their courtship. Chaim would be working security at the door of the Up and Up bar, and Miriam would bring him coffee just about every evening. So of course I had to start their engagement shoot by documenting that very moment. I set up the shot much as I would a first look at a wedding, and Miriam and Chaim got a kick out of this first look practice session. The couple first bought a cup of coffee at Caffe Reggio, and then Miriam came walking down the sidewalk with coffee in hand. For Miriam and Chaim, this was one of the most important moments in the photo shoot because, as they put it, this is a moment that has passed from their lives. Miriam now works in a different location, so sadly she cannot make regular coffee runs anymore.

Man wearing cap waiting on staircase for a Greenwich Village engagement portrait

Washington Square Park

With this shot under our belt, we next moved to the second big location of the night, the corner leading into Washington Square Park. It was on this corner that Chaim waffled between if he should or shouldn’t put his arm around Miriam’s shoulder. As she told me during our shoot, she was waiting for Chaim to make a move, and if he hadn’t put his arm around her that night, she was prepared to grab his arm and put it around her on her own. Well, I am happy to report that Chaim did indeed take the next step and Miriam and Chaim enjoyed a stroll through Washington Square Park on their date.

We lingered a while around the chess playing area, and then moved over to the fountains and arch. I should interrupt this love story with a bit of context for the neighborhood here. Greenwich Village has morphed into one of the most expensive and trendy parts in town, thanks in no small part to it being the home of New York University. The area is swarming with students, locals, and tourists of every economic bracket. It’s crowded, especially in the afternoons, and there is no way to avoid it. So be prepared. I always like my photos to have a less cluttered background – both in terms of things and people behind my subjects. Greenwich Village challenges all that, and be it walking down McDougal Street or taking a stroll through Washington Square Park, the number of people and things entering the frame are just a fact of life for this part of New York.

Couple sitting at chess table in Washington Square Park for a Greenwich Village engagement portrait

For our shoot, we were running short on time because we wanted to hop over to the Hudson River for sunset. While we didn’t have as much time for Washington Square Park, if you’re making this area part of your photo shoot then know that the park and surrounding neighborhood are packed full of photo opportunities. In the park itself you have entertainers and a dog run – all of which could all be fascinating photo ops for your shoot. Interacting with your environment makes for great photos. The fountain is turned on spring, summer, and fall, so make use of it by sitting on the edge and getting the Washington Square Arch in the background.

If you want a quieter environment for your photo shoot, don’t forget about Washington Mews, the small street where the language department for NYU is located. As you can see from Marisa and Colin‘s Greenwich Village engagement portrait, Washington Mews is a quaint little cobblestone street that looks out of place in downtown Manhattan. Definitely take photos here, but know that the Instagram crowd also knows about Washington Mews, and you’ll need to be strategic to keep them out of your frame.

The streets surrounding Washington Square Park have immense brownstones that look like something out of Edith Wharton’s old New York. These quiet streets are fantastic for shots of people walking, and if you are lucky enough to find a set of stairs without a gate, then by all means take a few photos. One hidden gem in Greenwich Village that most people don’t know about is the Minetta Triangle. It’s a tiny smidgen of a park at the corner of Minetta Street and Sixth Avenue that you can disappear into and feel like you’ve entered the Secret Garden.


Pier 45 – Hudson River Park

Couples dancing tango by the Hudson River for a Greenwich Village engagement portrait

As a big finale to our Greenwich Village engagement portrait, Miriam and Chaim wanted to walk to Pier 45 at the Hudson River Park. When we got there, we were greeted with not only a gorgeous sunset, but also a tango-dancing group that strutting at the end of the pier. I have to say, the night was truly magical. [I was doubly pleased because I am in the process of planning a trip to Buenos Aires, and I would love to photograph tango dancers there!]


Tips for Recreating Your First Date

Couple holding hands and walking on MacDouglas Street for a Greenwich Village engagement portrait

Recreating your first date is, in this photographer’s opinion, one of the best engagement shoot ideas…period. Here are a few tips to get your first date perfect, the second time around.

Be flexible. You can never completely recreate something from start to finish. In the case of Miriam and Chaim’s date, they actually started the evening at Washington Square Park, and then moved to the Up and Up bar. For our shoot we had to switch things up a bit. The photo shoot had to start earlier at the Up and Up because the bar officially opened at 5:00 p.m. As such, we had to get all of our images taken before the door got crowded. Secondly, Miriam and Chaim actually ended the evening at Max Brenner’s chocolate bar in Union Square. I keep my photo shoot to two hours because, frankly, unless you’re a professional model you will be sick of taking photos after two hours. We didn’t have time to take in the sunset on the Hudson River and make it to Max Brenner’s within the two-hour time frame, so the Max Brenner location was cut.

Couple toasting glasses in a restaurant

Indoor shots may be off limits. Taking photos inside private businesses such as restaurants or bars can get a bit tricky. Most businesses will not allow you and your photographer to waltz in and disturb other paying customers. If you’re going to be taking photos while a restaurant is in operation, you may have to settle for taking photos only outside, or sneaking a few photos at the bar. It never hurts to ask, however, because who could deny a couple wanting to recreate their first date?

For Miriam and Chaim, the couple wanted to include dinner at Monte’s Trattoria on McDougal Street. When we arrived at Monte’s, the restaurant was not quite open yet, but after some sweet talking from Chaim, the restaurant kindly let us in to take some photos at a corner table. The table where Miriam and Chaim first had dinner, I might note. While in the restaurant for our photo shoot, Miriam and Chaim ordered and paid for drinks, so the restaurant wasn’t out of money for the experience. In the case of visiting Max Brenner’s chocolate shop, the plan was to go in and buy some chocolate, thereby appeasing the retail gods and taking a few photos in the process.


Think of your photo shoot as a mini date. Your engagement portrait is going to be a shorter version of your much longer first date. For Miriam and Chaim, they didn’t want the evening to end and their first date lasted many, many hours. With only two hours to shoot, we boiled down the essence of what they did on their first date and made a plan accordingly. Consider the most important locations and activities of your first date, and make those your shot list priorities.


Include a first look. If you’re already married or living together, how about adding a first look or a few getting ready photos to the engagement shoot? If you have the same outfit you wore on your first date, or something even close to it, how about setting the stage so that your significant other sees you again for the first time. Recreating that moment when you first walked through the door and took his breath away is a wonderful photo opportunity.


Transportation is a fun photo op. When you live in New York City, getting around is part of the adventure. Did you take the subway to go from the restaurant to a bar during your first date? Don’t forget to include this part of the date in your photo shoot. Subway scenes are some of my all-time favorite images, and the New York City subway is chock-full of hidden nooks and crannies in which to steal a kiss. Of course, don’t touch anything.


Wear comfortable shoes. Most of my photo shoots involve lots of walking. Who wants to stay in one place for your entire two-hour shoot? Not me. Make sure you wear comfortable shoes, or bring them to change into during the portrait session. For Miriam and Chaim, moving from McDougal Street to the Hudson River involved walking nine blocks. Sadly, the NYC subway system works better north and south and it does east and west, and hoofing it is the best mode of transportation.


Enjoy the rest of the photos from Miriam and Chaim’s Greenwich Village engagement portrait, and give me a call if you’re looking to set up a similar style of shoot. I would love to work with you.

Greenwich Village Engagement Portrait Locations:

If you would like to see more images from my portfolio, like this Greenwich Village engagement portrait, then please visit my website – KellyWilliamsPhotographer.com

Couple photographed for a Greenwich Village engagement portraitCouple walking past Grisley Pear for a Greenwich Village engagement portraitMan looking at woman reflected in mirrored doorClose up on couple holding hands at table with woman wearing engagement ringCouple photographed for a Greenwich Village engagement portraitCouple photographed for a Greenwich Village engagement portraitRing photographed for a Greenwich Village engagement portraitCouple photographed for a Greenwich Village engagement portraitCouple photographed for a Greenwich Village engagement portraitCouple photographed for a Greenwich Village engagement portraitCouple photographed for a Greenwich Village engagement portraitCouple photographed for a Greenwich Village engagement portraitStatue of Liberty photographed for a Greenwich Village engagement portraitCouple photographed for a Greenwich Village engagement portraitCouple standing in front of Hudson RiverCouple standing in front of Hudson RiverCouple leaning against railing in Hudson River waterfront parkWoman hugging man from behind in front of Hudson RiverBacklit photo of couple in front of Hudson RiverMan lifting up woman's head with his finger in front of Hudson RiverCouple standing in front of Hudson RiverMan kissing woman's head with colored lights in front of Hudson RiverCouple leaning against railing with Hudson River at sunset in backgroundCouple standing in front of Hudson RiverMan kissing woman's head in front of Hudson RiverCouple standing in front of Hudson RiverCouple out of focus kissing with Statue of Liberty in backgroundCouple standing in front of Hudson River

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