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Jenna & Alex | A Lovely Navy Pier Engagement | Chicago, IL

Jenna and her friend Jill spent many weekends visiting Jill's high school sweetheart in his fraternity house, and every weekend was told tales and legends of a mystery man who she had never met - and that man was Alex! Every time she visited the fraternity house with Jill, Alex was always coincidentally gone for the weekend. But eventually, on a particularly chilly St. Patty's weekend in Chicago, Jenna finally met the mystery man she had heard stories about for so long.

When she first ran into Alex, she first took notice of his high energy levels from the drinking he had done earlier in the day prior to their meeting - she knew he was a wild one, but that he would be a great friend. And now, nearly ten years later, once a mystery man, and now her fiance, Jenna and Alex will soon be Mr. and Mrs. Napolitano!


Fiances, Jenna and Alex, smiling and sitting on the grass with the Centennial Wheel in the background


Jenna and Alex continued to develop their friendship over the following years, but 2020 was when they grew much closer. While the covid shutdown caused many people to be apart, Jenna, Alex, and their friend Stephanie were all lucky enough to have been hanging out when the shutdown went into place, and decided to continue surviving through the shutdown as the three amigos!

Like I mentioned earlier, this is when they began growing closer, and their fondness for each other continued to grow as they continued to hang out through the following year, until Alex had to leave for a Summer internship in June of 2021.

For those months he was gone, all Jenna could think about was Alex, with the only thing quelling her yearning for his return being their daily phone calls where they would spend hours talking to each other. After what felt like decades of separation, Alex returned from his Summer internship and his relationship with Jenna really took off! In the blink of an eye, they had become a couple by November of 2021!

Once they were together, Alex received a job opportunity of working for a mainline airline, but would have to relocate to Colorado for a year. When talking through their thoughts on the offer and about their future together, Alex realized just how much his love and admiration for Jenna had grown and knew she was the one for him! (Luckily, another position was available in Chicago, so Alex and Jenna never had to go long distance!)



Now, of course we have to tell you all about the proposal!! So, Jenna and Alex had made plans to go to the Margaritaville on Navy Pier after finishing the newest season of Outer Banks on March 5th of this year. But, little did Jenna know, Alex had already been conspiring with her family on a proposal plan that would take place on Navy Pier - so, Jenna's Margaritaville lunch was actually going to be her engagement celebration!

As they arrived at the Navy Pier in Downtown Chicago, the bright sun shined down on them while they walked along. Alex suggested they walk on the pier and enjoy the nice weather before lunch, but Jenna was very hungry since she thought the plan was to just go straight to Margaritaville! So, after some back-and-forth and convincing with the promise of drinks afterwards, Jenna finally gave in, and the plan was in motion.

Jenna and Alex will often leave post-it notes with sweet messages written in each other's lunch boxes, on pillowcases, etc., but they had never handed the other one of those post-it notes directly. So, Jenna was pretty confused when Alex began handing her post-it notes on their way to the farthest part of the pier. Once they reached the end, Alex pulled one last post-it note from his pocket, the most important one there was, and handed it to Jenna.

On the note was written, "Will you marry me?" accompanied by Alex getting down on one knee. and formally asking Jenna to be his wife. Jenna followed with a gasp and replied "Are you shitting me right now?! YES!" As Jenna and Alex shared a celebratory kiss, cheering could be heard behind them, and when they turned around Jenna saw both of their parents and Alex's cousins. After greeting one another, the gang headed back towards Margaritaville where they shared a celebratory meal and some yummy drinks!

To Jenna and Alex, I am so glad to have met such fun and kind souls that truly enjoy whatever they're doing as long as they have one another. It warms my heart to witness such a bright and youthful love that will age just like fine wine! I had an absolute blast with you all while capturing such a lovely Navy Pier engagement session! I cannot wait to celebrate your eternal love next July when you'll officially become Mr. and Mrs. Napolitano! See you, then!!


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I like turtles!


Keegan Goss
Keegan Goss
Sep 30, 2023

Awesome pictures! Can't wait for the wedding!


Tabitha Anderson
Tabitha Anderson
Sep 27, 2023

Pictures that prove true love! Beautiful! 💕


Just stunning…every single photo. You captured these two lovebirds beautifully! 💕


Jenna Lefley
Jenna Lefley
Sep 26, 2023

From Wendy Napolitano:

Beautiful photo session that captured so many great images of Alex and Jenna. The location shots turned out fantastic and they both look amazing!!

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