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Chicago Engagement Session {Megan & Rich}

What can we say about Chicago that hasn’t been said? The place is dreamy. We can definitely confirm that Megan and Rich elevated Chicago with their sweet charm and phenomenal personalities. This never felt like an engagement session. In fact, it just felt like walking, laughing and getting to know each other around Chicago. To top it off, our evening ended back at their place with Rich playing one of his many guitars for Megan while enjoying the incredible view with our newest friends. Megan and Rich, we are such big fans and we can’t wait for New Year’s Eve!

How they met

Megan & Rich met at work and worked closely together as friends for about a year before dating. They worked from their respective locations (Denver & Chicago), meeting in person for the first time at a work dinner in Philly. The two squeezed in together at the end of the table and shared fish and chips. They continued to see each other at work events and realized there was a spark when Rich visited Denver where Megan lived. Both wanting something more, Rich went back to Denver to take Megan on a date and the rest is history! Megan moved to Chicago three months after their first date!

How did he propose?


“We were supposed to visit Washington D.C. early April 2020 but had to cancel because of COVID.  It was Easter weekend and Rich showed up from the grocery store with plastic eggs saying, “let’s do an egg hunt in the apartment since we can’t be with family” (this is Rich to a T!). We had a nice dinner, then he suggested we hide eggs in separate rooms. I walked into the living room and thought “what’s wrong with him?” All the eggs were in plain sight! Then I saw a note sticking out of one. “What lies inside is waiting in the other room.” I walked into the guest room and he was on one knee. He had a photographer and big plans for D.C., but our COVID engagement was perfect.”

What do you love most about each other and your relationship?

Megan: “My favorite thing about Rich is his heart – even as a coworker he was so generous with his time and knowledge. Now as my fiance, he wants the best for us and shows it in little ways like surprising me last night with homemade hot chocolate and peanut butter frosting.  He is unassuming, never judges me and always means well.  There’s never an ulterior motive or negative assumption.  I couldn’t be more grateful for him.”

Rich:  “I can write a book about Meg. Even before we dated things were just easy with her. Easy to talk to, work with – I have never had a bad day with Megan Gaylor. The thing I love most about Meg is her love for life. It doesn’t matter what the situation is – Meg is there to enjoy it and live it to the fullest. It has rubbed off on me in a tremendous way. I find myself wanting to do more, explore more things – with Meg. Seeing the beauty in things even when they don’t appear beautiful on the surface. She truly can walk into a room and change the whole dynamic. Her love of life is something special and she has an endless amount of it to give. It’s infectious and if you are fortunate enough to experience it, I can promise you she will not be a person you forget. She brings that same joy to me every day.”

How sweet and romantic is that? Megan and Rich, we are so excited to be such a huge part of your special day.

Ready to book your own Chicago Engagement Session? Let’s chat!

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