Rooftop Surprise Proposal in Washington DC

“Our love is resilient. We both know life is not perfect and we are not perfect.

Through the ups and downs of life, we both just want the other to be happy, but more importantly, we want to be there for each other
in the good and bad times. We know the commitment we have made to each other and we always put that first.”

– Dylan


I recently read that the greatest compliment a woman can give a man is the desire to have and raise his children. The questionnaire I send to my engagement photo session clients includes the prompt, What is the best thing about being with him/her?

As I wrote this photo feature for my website, Sonali’s response got me misty-eyed:

“I cannot wait to one day have our kids have this kind of role model to look up to. It’s the most inspiring thing to have someone in your daily life who genuinely makes a difference in other people’s lives. Dylan is incredibly passionate about his work; it motivates me to work hard, but also find purpose in it.”

best rooftop proposal photography, dc photographer, surprise proposal, dc engagement
best rooftop proposal photography, dc photographer, surprise proposal, dc engagement

How They Met

Dylan had noticed Sonali in grad school at GWU, and one day when they both happened to leave class late, Dylan seized his opportunity and ran after her. They had their first conversation on the metro; a simple, but life-changing encounter.

Sonali saw Dylan waiting for the same train and decided to approach him. They immediately connected. Dylan had something that naturally made Sonali feel safe from the minute she met him: “I barely knew Dylan, but I knew I could rely on him.”

“Just as my metro stop was approaching…Dylan asked for my number. He texted me a half hour after I got home (the longest 30 minutes of my life). Two weeks later, we went on our first date and now it’s been 3.5 years together with a wedding in December!”

When They Fell in Love…

Dylan knew Sonali was the one when they ended up spending six straight hours talking - on their first date!

“As much as I wanted to listen to her, she wanted to listen to me. Sonali always put others before herself and her kindness always came through whenever I spoke to her. It also doesn’t hurt that when I see her, I find myself not being able to look away.”

Sonali says, “Something that constantly reminds me of why Dylan is my “one” is his love for family. Family is everything to me, and he always goes out of his way to do the little things for them. He has the purest of intentions for me, he has this go-with-the-flow personality (something my Type A self is trying to learn), and never says no to having an impromptu dance party with me.”

How He Proposed

Sonali and Dylan now live in Florida and Texas, but Dylan wanted to propose in DC because of how much it meant to them as a couple; it brought them together. Dylan invited Sonali to a work conference (not actually taking place). She knew how much his new position meant to him, so she didn’t think twice about the trip.

That’s when Dylan called me to be his photographer. As he described his vision for their proposal and engagement with excitement and confidence, you could hear in his voice how much his soon-to-be fiancée meant to him, how much he loved her.

Together we fine-tuned timing and location details. Dylan had chosen 101 Constitution Ave, a spectacular DC rooftop I’ve photographed before, with a perfect view of the heart of DC - the National Mall, Capitol Building, museums, and gardens. He’d coordinated a private driver and worked with the event coordinators at 101 to set up a table with flowers and champagne on the private rooftop. Dylan told Sonali they had a nice reception that afternoon, so she got dressed up for the occasion.

Dylan did a fantastic job of keeping his proposal a big surprise until the last second. Sonali says, 

“A private ‘company’ car came to pick us up and of course, all of my Olivia Pope dreams were coming true. His ‘boss’ even called him about said ‘event’. Once on the rooftop, I saw tables being set up and started walking towards them.

Dylan pulled me back and said, ‘Babe, this is us.’ I was utterly confused and said, ‘No, Dylan, the event is over there.’

I turned around and there was Dylan, dropped to one knee, reminiscing the last three years of our lives together.

He asked me to marry him. Nothing else mattered in the world.”

Their Engagement Celebrations

Dylan had a weekend full of surprises for Sonali. He had planned a celebratory dinner at one of their favorite restaurants with their siblings and best friends from home, and 30 of their closest friends from around the country. Last but not least, instead of Dylan flying back to Houston, he flew back to Jacksonville where Sonali is from so that they could see her parents.

101 Constitution Ave’s staff were amazing to work with and it was a great bonus that Rachel had done a photo shoot there before so she knew all the logistics of the location.”

– Dylan

How did you choose your engagement session location and outfits?

Sonali:

My friends, mom, and sister-in-law were a huge help in this. I always opt for black clothing, but everyone kept pushing me to wear a light color. I thought they were just tired of my boring clothing choices. Later found out that it was actually Rachel’s advice to wear lighter colors for the pictures! I started searching for ideas thinking this event is a big deal to Dylan and I wanted to dress nice. Dylan also had bought a new suit so of course we had to coordinate (something he knows I love!). Everything else was Dylan’s doing, but it makes complete sense as to why it had to be in DC. 

Of working with Lincoln Photography, Sonali and Dylan say…

Sonali:

Dylan was the one who found Rachel to photograph one of our most memorable moments. I will say that these pictures are my most cherished and I cannot wait to show our future kids someday. Thank you so much Rachel for being so easy to work with, and always keeping up with us as a couple.

Dylan:

I heard about Rachel through just combing the internet for DMV photographers and noticed her pictures are great. Rachel was absolutely amazing. She spent the time with me going over how I was going to propose and she gave great advice on the layout and even the color of the suit I wore to make sure It went well with the setting. The pictures were stunning and she made taking pictures so much fun. I'm so grateful to Rachel for beautifully capturing, up to this point, the most important moment in my life.

best rooftop proposal photography, dc photographer, surprise proposal, dc engagement
best rooftop proposal photography, dc photographer, surprise proposal, dc engagement

“Our love and bond is the most unexpected. We are so different in personality and interests, but our core values are completely aligned. I enjoy learning from our love and him. I never want to stop growing and building this life together because I truly think we have the rare balance of supporting each other in everything while also pursuing our own goals.”

– Sonali

“As much as I wanted to listen to her, she wanted to listen to me. Sonali always put others before herself and her kindness always came through whenever I spoke to her. It also doesn’t hurt that when I see her, I find myself not being able to look away.”

— Dylan

best rooftop proposal photography, dc photographer, surprise proposal, dc engagement

“I cannot wait to one day have our kids have this kind of role model to look up to.

— Sonali

"Whatever our souls are made of, his and mine are the same."

–Emily Brontë

best rooftop proposal photography, dc photographer, surprise proposal, dc engagement

Engagement sessions are a fun way to get used to being in front of the camera, and to get to know your wedding photographer before your big day - one less thing to worry about at your wedding! During my engagement photo sessions, I always give plenty of direction so you aren’t left wondering what to do. You don’t need to know how to pose for engagement photos; that’s my job! Many couples I’ve worked with tell me first thing: we are really awkward in photos! I’ve never found that to actually be true with just a little posing guidance from an experienced photographer to bring out your natural, happy smiles. Together we’ll create loving images filled with real emotion that you’ll treasure and enjoy sharing with your family and friends.