West Hartford Surprise Proposal and Engagement Session

A Chilly West Hartford Surprise Proposal Followed by a Blue Back Square Engagement Session

If you’re anything like me, then the lack of snow in Connecticut this winter has been a little disappointing. With no snowmen to build, I’m sure you’ve had to keep yourself busy in other ways. Me, too, dear reader. Me, too. For example, I ran an engagement session giveaway contest in January. Then, I shot one of the winning couple’s sessions and had some delicious ice cream. But what I’ve been really quiet about until now is the fact that there was one more winning couple. Read on and I’ll tell you all about why and how I became Juliana and Dan’s West Hartford proposal and engagement photographer!

Update 3/17/20 @ 9:03 AM: This session has been published on howtheyasked by The Knot!

This is kind of exciting, everyone. howtheyasked by The Knot has published Juliana and Dan’s proposal story, featuring one of the images from their session with me! Please check it out here. Thanks, howtheyasked!

It started with a contest entry, a small request, and a plan

When I first heard from Dan and read through his answers to my engagement session giveaway, I had…questions. Per usual, I invited him to chat in person and then it all made sense: Dan was hoping to morph this engagement session into a surprise proposal!

Dan and I hit it off early on: we both have computer-related backgrounds and like Seiko watches. So when he told me that his significant other, Juliana, was a professional violinist, I was intrigued about how he planned to incorporate that into his proposal. His locale of choice was West Hartford’s Blue Back Square, one our state’s most happening city spots.

Sometimes, the best laid plans fall apart. Here comes to Dan, executing plan B.

His plan was genius: Dan was electronically posing as “Alice,” a woman who was planning to hire Juliana to play a private gig in Blue Back Square. Dan and I would each hide somewhere separately, then when Juliana arrived looking for Alice, Dan would jump out and surprise her with a marriage proposal. Sounds simple, right? Well, the only other surprise proposal that I’ve photographed is my own. So while I welcomed the chance to capture Dan’s surprise proposal to Juliana and then run through a West Hartford engagement session with them, I was admittedly nervous!

The best element for a West Hartford engagement session: freezing weather

My assistant, Mike, and I arrived at Blue Back Square way ahead of schedule. Because, again, I was nervous! We scouted the area, made contact by phone with Dan, and got into position. A few days prior, Dan and I had one last meeting to make sure that we were still on the same page. I offered Mike as an actor in his plot, playing fake Alice’s fake son. Mike looked out for Juliana and then started the conversation when she arrived.

What we weren’t expecting, however, was for her to head into a store! In retrospect, it makes perfect sense: it was 6:00 PM, getting dark, and a few degrees below freezing. Dan was actually across the street, watching everything. We began texting each other, which was hard because I had gloves on (and was a little chilly myself). I wish someone were taking pictures of me, as I must have looked pretty comical switching my gaze from Dan’s location, to my phone, over to Juliana’s location, then back to my phone. At least the movement warmed me up a little!

Finally, Mike, who was pretending to contact Alice, texted me that Juliana was going to wait inside the store until Alice arrived outside. This was it: we weren’t going to be able to get Juliana to Dan’s spot. By now, I’m sure that Dan was really nervous about what was happening and what I was going to do about it. So I made a game-time decision…

A familiar face as bait

So, what did I do to get this surprise proposal in motion? I told Dan to come outside before Juliana. Now, this all happened in a matter of minutes, so there wasn’t much time to consider how Juliana might react. This WAS NOT the way Dan and I rehearsed his proposal, but we had to make due! Dan made his way across Isham Road, stood in front of the store’s window, and waited for Juliana to see him and come out, violin in hand. It didn’t take long and things were in motion.

It worked! Juliana spotted “Alice” and came outside.

The elements of a surprise proposal

After Dan proposed and I photographed his and Juliana’s West Hartford engagement session, I asked him if he had any tips for all the folks out there planning to propose. He had three that I think everyone should hear!

Dan moves into position as Juliana follows.

1. Figure out your partner, then mold your surprise proposal appropriately

Juliana’s passion and career is the violin. So from the get-go, Dan knew that that was an element which he needed to incorporate into his marriage proposal. He makes a great point! Thinking back to when I proposed to MaryKate, playing on her love for travel enabled me to get her to Chatham Beach without too much suspicion. Likewise, Dan donned a persona and actually booked his future fiancée to play a gig at his desired proposal location.

2. Let your significant other know just enough to get them where you need them to be

This follows directly from #1. To Dan’s point, you could be proposing to the love of your life at home, their workplace, or an exotic vacation somewhere. Regardless of where you’ll be popping the question, you need to get them there somehow! What’s more, you need to get them there without them knowing exactly why they’re going. I will always think that Dan’s approach is great: he plain old pretended to be somewhere else, even going as far as creating a fake email account to contact Juliana!

3. If there are multiple people involved in the plan, talk to all of them yourself

This one’s really important. Here, Dan is pointing out that clear communication and trust are key factors to a surprise proposal. Anyone who is involved needs to be on the same page with everyone else, most importantly you, the proposer! The further I move into my portrait and wedding photography career, the more I appreciate the importance of establishing trust early on with clients. If I couldn’t earn Dan’s trust, there’s no way he would have decided to move forward with me as his engagement photographer.

Back to the big show

Now, let’s get back to Dan’s proposal to Juliana! I’ll keep it short at this point: their moment was magical. Despite the cold, Juliana and Dan’s love took over Blue Back Square.

No, he’s not tying his shoe!
Dan actually got onto one knee twice. Juliana was so excited that she needed a hug before he finished his proposal. This is true love!
Juliana checks out her newly-engaged ring finger.
One kiss seals the deal. By the way, passers by were excited, too. Many people stopped to congratulate the nearlyweds.
Here, Dan’s smile says, “I did it!”
I think Dan was tweeting here. (just kidding)
She said “Yes”! Look at that smile.

Ending with a West Hartford engagement session

Shortly after making it official, Juliana and Dan spent some time with me for an engagement session in Blue Back Square. The city at night made for a perfect backdrop!

A photo op for the nearlyweds.
Walking away, elated and ready to continue their love story.
Taking a second to dance the night away.
Love overpowers darkness!

Time to say goodnight, but remember these surprise proposal tips

And there you have it. Here’s to wishing Juliana and Dan a lifetime of happiness…but first, a good few months planning their upcoming wedding! And to those of you out there who are planning to pop the question, remember Dan’s tips for planning a proposal:

  1. Incorporate your significant other’s personality, passions, and likes into your proposal.
  2. Tell your partner just enough to get them where they need to be, when they need to be there.
  3. Communicate with all of your co-conspirators directly.

Lastly, if you’re planning a surprise proposal of your own, needing an engagement session, or ready to talk about your wedding photography, drop me a line over on my contact page. Thank you for reading!

From your proposal to your wedding day, I’ve got your photography covered.

Click below, send me a quick message, and let’s talk about your needs!

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