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Hey! Welcome to the Alexandra Lee Blog! Grab a beverage, sit down, relax and scroll through Alexandra Lee weddings and sessions!


Gloomy Lincoln Park Session

Oct 30, 2018

4/4 for my marathon weekend of engagement sessions! AND IT ENDED WITH A BANG! Caitlin and Ryan were amazing! So sweet and so down for anything! It even rained halfway through our session, but we just kept trucking and they just kept smiling!

The two of them met “through mutual friends” on Hinge! After some talking decided to go on their first date together. They went to Sheffield’s Beer & Wine Garden in Wrigleyville where they got dinner and drinks. Caitlin, as she puts, “awkwardly” sat on the same side of the booth as Ryan. For some people, that’s a deal breaker, but for Ryan he just thought it was funny and let it slide. Now they always joke about it.

Ryan is a huge White Sox fan, where as Caitlin is a Cubs fan. One day, they were going to a Cubs game with their moms and sisters. During the first few innings, Ryan was being unusually quiet. After the fourth inning, Caitlin found out why. On the Jumbotron, “Caitlin Mary Winkelman, Will You Marry Me?” popped up. Ryan brought her down a few rows, and asked her to marry her. (Huge deal for this White Sox fan to propose at Wrigley!) After the game, they went to Sheffield’s where Ryan suggested they take a photo at their first date spot and show their family. After, Ryan took her to the back bar where he surprised her again with all of their best friends and the rest of their family waiting to celebrate!

The two of them laugh a lot together and are super goofy together. Ryan loves how much Caitlin makes him laugh and how sweet she is. He says she’s got a heart of a lion and that she can talk to anyone which makes new places or events fun and easy. He loves that she lets him do the things he loves and that she is truly his best friend. Caitlin loves how goofy he is and his sense of humor. She says he always goes above and beyond to help others and is so selfless and caring. She loves his heart of gold and loves everything about him!

They love to have date nights together trying new restaurants with a well-crafted cocktail. When they aren’t out and about, they like to just stay in, watch a movie, order takeout and drink wine.

They are getting married next July at Chevy Chase Country Club! It’s going to be amazing and I can already tell it’s going to be so much fun and full of tons of laughter! I can’t wait!


  1. Ryan

    December 4th, 2018 at 7:02 pm

    Such the perfect chicago couple, in Chicago weather. Beautiful!

  2. Chuck

    December 4th, 2018 at 11:29 pm

    Amazing couple and fantastic pics! These kids run in town. If the wedding is anything like their hospitality, it will be first rate!

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