Jay and Jessica admit that their first few interactions after meeting each other on a dating app were a struggle. “Jay—the kind, southern gentleman—would reach out, ask questions and try to engage,” says Jessica. But being a born-and-bred New Yorker (and self-described dating pessimist), she would respond sometimes a day later with one-word replies. The breakthrough came when Jay asked Jessica about dogs, which turns out to be her soft spot. The two soon discovered they had a lot more in common and after that everything started falling into place. Not surprisingly, the couple now share a dog named Lionel, who made several special appearances throughout their big day.

Blue Hill at Stone Barns
Date held
Sat Jun 10th

Is there a memory of each other on your day that stands out most in your memory?

Jay: Our first look. Jess was very private about the dress selection process with the understanding that it could be bad luck. I was very excited to see her in her dress and our arrangement to see each other on her parent’s terrace overlooking central park. It was everything I could hope for.

Jessica: The ceremony and saying our vows to each other. I had secretly been writing my vows since our third date. I had a note in my phone that I would add to whenever a thought came into my head. It was incredible to finally put my three years worth of thoughts on paper and say them to Jay in front of everyone we love in our lives. Also during the ceremony we had a special moment when the rabbi put Jay’s father’s (who had passed away five months before our wedding) tallit, around us. I swear in that moment I could feel him surrounding us.


Why did you decide to have a First Look?

Jay: We wanted to spend as much time as we could with each other and our bridal parties as they traveled from all over the country. Additionally, we wanted some element of our wedding photos to be in New York City and thought that was the ideal solve.

Jessica: Jay and I love my family’s apartment and have so many memories there, especially on the terrace, which overlooks many of our most favorite places in Manhattan. We thought seeing each other for the first time on their terrace would just add another special memory to a place that already means so much to us. We later found out that all of my bridesmaids were able to watch through the windows throughout the apartment and Jay’s groomsmen could see us from their room at the Mandarin Hotel.

I was very excited to see her in her dress... It was everything I could hope for.


It was kind of a joke at the time how great it would be to get married at Blue Hill, but in the back of my mind I knew it could be true one day.



What was the easiest wedding planning decision you made?

Jay: The location – Jessica had taken me for my birthday long before we were engaged. It was kind of a joke at the time how great it would be to get married there but in the back of my mind I knew it could be true one day. We looked at a few places all of which were very nice but I was holding out for our visit to Blue Hill. When we got on site it was a no-brainer and we fell in love with the location all over again.

Jess: For me that’s a tie between venue, planner and photographer. Jay and I had been to one of my friend’s weddings, which had been done by Fête and it was absolutely magical. I pretty much decided after that wedding that Jung, Josh and Allison from Fête were going to plan my wedding. We never even met with another planner. At this same wedding Ira took a photo of Jay and me. It happened to be the very first wedding Jay and I ever went to together and we ended up loving the photo and treasuring it. It only made sense to ask Ira to photograph our wedding day.


What was the most difficult decision you had to make?

Jess: This is silly but I couldn’t decide if I wanted to wear a second dress to dance in. I looked for months and couldn’t find anything I loved as much as my original Vera gown and had pretty much given up which I was fine with. When I saw the weather for the day of our wedding and realized it was going to be a warm evening I took one last look around. I found something I loved and was so happy I did because after 2 hours of straight dancing and the hora it was nice to be able to slip into something a little lighter.

Jay: I wanted to get my groomsmen a unique gift, one they may not have gotten before at other weddings. I ended up getting custom bobbleheads, something that they could keep on their desks forever.

It was incredible to finally put my three years worth of thoughts on paper and say them to Jay in front of everyone we love in our lives.



What is the best or most helpful planning advice you received?

Jay: Take your time. Don’t rush into decisions. Jess and I ended up having a 2-year engagement and still believe it was the best decision for us as a couple. We never felt rushed and got to work with every vendor we had originally hoped to work with because our date was so far out.

Jess: Find a planner you trust and lean on them. There were a few decisions that I just couldn’t figure out what I wanted, so I asked Jung and Allison their opinions and of course they always ended up being right.


What aspects of your wedding most reflected your personality?

Jay: Both Jessica’s dad and myself love cigars and Jess and I love whisky, so we wanted to have a lounge area where you could smoke a great cigar and drink a fine whisky. We were lucky to get custom Fuente cigars for our big day and a great selection of classic whiskies. Also, we knew it was going to be a long day so Jess and I thought it could be fun to have a “recharge” section which included phone chargers, 5-Hour Energy drinks and iced coffee so you could recharge your phone – and your self!

Jessica: So many. We wanted our wedding to feel uniquely like us. Our dog Lionel walking down the aisle was pretty unique. For the late night food, Fête created an amazing kiosk of all of our favorite foods (grilled cheese, reubens, truffle fries, milkshakes) and called it “Lionel’s Shack” – although Lionel had long left and gone to bed it was fun that he was there with us in spirit through the kiosk. We, as well as our guests, seemed to love our “How lucky are we” neon sign. This is a phrase Jay and I have said to each other since the beginning and it was fun to see everyone embrace it.

How quickly the entire day goes by... I wish I could have frozen time.



Did anything surprise you?

Jay: Our rabbi did an unbelievable job summarizing our relationship and who we are to our friends and family.

Jess: How quickly the entire day goes by – from the makeup and hair to the wedding itself. I wish I could have frozen time.


Would you do anything differently?

Jay: We had three weddings leading up to our wedding in the span of six weeks. I didn’t realize it at the time but it wore me down and I ended up getting sick just a week before our own wedding. While I felt fine on the day of, I wouldn’t recommend tons of travel right before the big day.

Jessica: I was a complete mess the week of the wedding because of the weather. It kept going from sun to rain to sun to rain. I think everyone, including Jay and Allison, wanted to kill me. Of course on the day of the wedding it turned out to be absolutely gorgeous but I wish I had spent a little less time the week beforehand worrying about it.

'How lucky are we'... This is a phrase Jay and I have said to each other since the beginning and it was fun to see everyone embrace it.


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  • Photography

    Ira Lippke

As the founder and creative force behind The Day, Ira Lippke brings 20-plus years of experience creating compelling images to every wedding he documents. “One of the best compliments I’ve ever received,” he says, “was from a planner who said I was the only photographer she knew who had so much experience but whose heart and soul was still so strongly in their work.”

Ira Lippke