Andrew + Ophelia ~ The Drake ~ Chicago Proposal Photography

When Andrew emailed me a month ago to tell me he was interested in having me document his Chicago proposal to his long-time girlfriend Ophelia, I was super excited. He and Ophelia live in Orlando, but were planning a trip to Andrew’s hometown, Chicago, to celebrate his completion of the bar exam. (Yes, he planned all of this while studying for the Bar! Go Andrew!!)

He planned a whirlwind of a day for Ophelia in hopes of catching her completely off guard – and it worked! They flew in Thursday morning and hit up a ton of spots in the city – finally landing them at the gazebo outside The Drake Hotel just before dinnertime. Andrew and I followed our carefully crafted plan and when he popped the question Ophelia was completely surprised! (Success!)

It was so cute to see her excitement and all the questions she had for him after the fact about how on earth he managed to pull this off. 🙂 I loved it! As always, I was SO honored to be a part of such a huge moment in my clients’ lives – and the session afterwards was so much fun because they were so stoked to be together and so excited about the engagement! 🙂 You can just feel the love in these pics…


It was a gorgeous night in Chicago…

They made it!!!  The original plan was to have Andrew set his camera on timer along the back wall, pose to take a picture together (but really the camera would be on video), and then pop the question – catching it all on film! However, this guy, Smiles, was sitting in the gazebo reading when I showed up – so I filled him in on what was happening in the location and asked him if he would rather move so the space could be clear, or if  – when Andrew went to set up his camera – he’d like to ask them if they wanted him to ‘take their picture’ instead, but to really record the whole thing. Smiles was SO excited about being a part of something so awesome – so he was all about playing along. However, after the fact we realized that apparently he didn’t follow Andrew’s directions very well and hit the camera shutter button instead of the video button…. so… no video… which was a bummer. But either way – I think it really helped to throw Ophelia off so that she really wasn’t expecting a proposal!!)

And now, a little mini-session after he popped the question!  They’re SO happy – I love it!!! 🙂


He even did an amazing job on the ring!!! Beautiful.

We ended the session here, but then as I was walking away to catch the bus – I heard some squeals and turned around to find Ophelia doing a happy dance & I couldn’t help but capture it!!


Andrew and Ophelia, I hope you guys have a fabulous time in Chicago celebrating the start of a new chapter in your lives together!!!  Congratulations!!!  xoxo!


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Christy & James are Chicago based but happily travel anywhere in the world that beautiful love stories take them!