Promontory Point & University of Chicago Engagement | Kailin & Winston


I loved meeting Kailin and Winston for their Promontory Point & University of Chicago engagement session. We met up for sunrise at a place where they love to hang out. Kailin brought the most amazing pumpkin chocolate chip muffins and Winston was all about the coffee. I can’t blame him. It was early. 🙂

We enjoyed breakfast, laughs and walking along Lake Michigan with the hazy skyline in the distance. When we all woke up a little, we headed over to the University of Chicago where they spent many lunch hours hanging out. I am so excited for their wedding next June.

How They Met

This cute couple met on a dating app about two years ago. It turns out he was going to school about six blocks from where she was currently working, so they spent many lunch hours together. Their first date was at La Cathedral, over chilaquiles. (Sounds like the perfect date to me!) Their second date was to watch Stranger than Fiction, which was filmed at La Cathedral.

Their Relationship

Though both of them are from the East Coast, their love story is in Chicago. Throughout the past two years, they’ve enjoyed exploring, biking, picnicking, and celebrating at Big Star in Wicker Park. Winston has finished Law School, and Kailin has started med school. Kailin also says that Winston is an amazing chef.

How He Proposed

Winston proposed a few weeks ago, complete with a trip back to the restaurant where it all began. How sweet is that?!


To see more engagement sessions like this one, head over here.

If you would like to know more about booking your wedding with me, contact me here or email me at

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