Get inspired not only by Cara and Sean’s sweet celebration, but also by their “aww”-inducing proposal story. All photos by Kenny Kim Photography.

Sean, on how he and Cara met…

“On May 7, 2013, I received the following Facebook message from Allie Detwiler, who I’ve known since high school and who just so happens to be Cara’s best friend.  Note: I hadn’t seen or talked to Allie in maybe 6 years.
Allie: “Hi! How are ya?! Random question for you… ARE YOU SINGO? I wanted to set you up with a friend of mine… in Chicago!”
My response:  “I am super singo actually, who’s this friend?”
After telling me a little bit more about her best friend Cara, whom she met at U of M, Allie asked me if I was interested. “Sure,” I replied, “I’m down for some dating…hook a brother up!”
So at this point in the story we have a “super singo” man who is “down for some dating.” Fast forward 2-3 months and we have a “super taken” man who is madly in love and “already thinking marriage.”  But I digress. Let me back up and explain how our courtship went down….” 
“My Facebook conversation with Allie certainly piqued my interest, so I chose to send Cara a Facebook friend request right away. A little over 2 hours later, she said “YES”! I used the opportunity to immediately begin Facebook stalking her profile…I really liked what I saw. Judging by her pictures, she was beautiful, seemed to be really close with her family and had an amazing sense of fashion. I was officially interested, but I didn’t want to come off as being desperate, so I waited 5 days before sending her a Facebook message. This happened to take place on May 12 (which was Mother’s day – yeah I know, odd timing).”
“During this initial Facebook conversation I mentioned that we should “definitely get together for a drink” sometime. Cara was heading on a trip to Australia soon – for 10 days – but we agreed that it’d be fun to meet up after she returned. Cara gave me her cell phone number and we proceeded to engage in some casual texting for a couple days. Then she was gone…headed to Australia for 10 days, where I feared she might meet a handsome Australian surfer and fall in love, before I was ever able to meet her. The thought terrified me, so I decided to text her the day she returned back to the US.  I had to secure a first date with her ASAP.
We met up for drinks on May 30 at Luxbar, one of my favorite bars in Chicago’s Gold Coast. When she walked into the bar I realized she was even more beautiful in person, which made me even more nervous than I already was. But she was so easy to talk to and there was never an awkward moment. Fifteen minutes into our conversation I could already tell that she was a very special girl and unlike anyone I had ever dated before.”
“I walked her home after we left the bar and during our goodbye I went out on a limb and told Cara that I wanted to see her again soon. I told her that I didn’t want to play games and that I wasn’t going to wait 3 days before texting her, like guys are trained to do. It was Thursday and I wanted to see her again at some point over the upcoming weekend. There needed to be a second date ASAP.
Luckily for me, there was more than a second date (obviously). But what you probably didn’t know is that after our third date Cara and I literally began seeing each other every single day. She was so much fun to be around and I didn’t want to go a single day without seeing her. She was smart, funny, and brought out the best in me. I got hooked on her very quickly, but it took a little time and effort to reel Cara in. Finally, on July 5, almost 2 months after my Mother’s Day Facebook message, Cara agreed to officially become my girlfriend. And twelve months after that, she said “Yes” and became my fiancé. It was the happiest moment of my life.”

Cara and Sean, on how they knew they were the perfect person for each other…

“We just clicked. From the very first date everything felt so natural and fun. In fact, after Date #2, Cara sent a text to her mom that said, “I think I’m going to marry him.” When you know, you know!”

Cara, on how Sean proposed…

“Sean told me that his company had just signed a big client and that his coworkers wanted to celebrate the accomplishment. One of his managers has a boat, and he said the plan was for a group of the guys at work to take the boat out the evening of Wednesday, July 23rd, and dates/spouses were invited. Wednesday rolled around and I came home from work a bit early so that I could get ready in time to make it to the boat. We headed out to catch a cab, Sean carrying a six pack of beer for the “friends” who we were meeting on the boat. As we approached the dock Sean explained that his manager had hired a boat captain to take us out that evening so that he wouldn’t have to worry about driving it. We were greeted by Captain Chris when we got to the boat, and he told us to make ourselves at home until the other guests arrived.
Unaware that I was making everything 10 times more difficult, I complained to Sean that I was cold and that I was going to go sit in the indoor part of the boat to warm up. Sean said it was warmer in the sun and that I should join him out there instead.”
“…At this point Captain Chris asked if we wanted our picture taken since he said he generally takes pictures of all guests that come on the boat. I thought this was a fairly odd proposition, but anyone who knows me knows that I never turn down a photo opp, so I willingly obliged. The next thing I knew Sean was hugging me, and saying sweet things like how much he loved me and how special the past year had been… and then all of a sudden he was down on one knee! I immediately started to freak out. He continued to say the sweetest things and I was literally jumping up and down before he could even get his question out. Sean asked me to spend the rest of my life with him and placed the most beautiful ring in the world on my finger! I said “YES!” a million times, completely overwhelmed with love and excitement.”
“A moment later Sean went inside the boat and then reappeared with a huge bouquet of roses and a bottle of champagne. He thought of everything! Sean then informed me that the whole story about his coworkers joining was obviously a ploy, and that Captain Chris would actually be taking us on a private boat ride on Lake Michigan for a few hours before our dinner reservation at Mastro’s Steakhouse. I was sooooo excited! I called my parents at their home in Michigan and screamed the good news and my parents screamed back with joy through the phone. They had already had a trip planned to come to Chicago that Friday, so they were soooo excited to get to see us in a few days to celebrate. 
When we arrived at Mastro’s following our beautiful boat ride, the hostess led us back to a table where seven people were sitting with their menus covering their faces. All of a sudden the menus dropped, and there sat Sean’s family and mine!!! My parents had somehow hidden the fact that they had arrived to Chicago two days early – I burst into tears on the spot! I was already floating, but having family there was truly the icing on the cake. We spent the rest of the evening and weekend celebrating with our families, and I don’t think I stopped smiling one time.”

Cara and Sean, on why they decided to tie the knot in Chicago…

“Even though we are both from Michigan, we met in Chicago and started our relationship here. We considered other options, but in the end, Chicago is home for us now. We looked at several different venues and The Peninsula just felt perfect… it is gorgeous and dazzling yet classy and intimate.”

Sean, on his favorite memories from his wedding day…

“Other than the obvious favorites of seeing Cara walk down the aisle during the ceremony, I would have to say it was the “first look.” I waited anxiously on the terrace of the Peninsula Hotel for what felt like an hour, but I’ll never forget turning around and seeing her for the first time…wow!”

Cara, on her favorite memories from her wedding day…

“This is so difficult! The entire day honestly felt so magical. We were blessed with perfect weather, and it was amazing having all of our favorite people in one place to celebrate our love. One of my favorite memories from the day was my first dance with Sean to “Sweetest Love” by Robin Thicke… we did our first dance right after we made our grand entrance into the reception… and as the song was coming to a close our band transitioned into playing “Uptown Funk,” at which point our whole wedding party busted out into a choreographed dance with us. It was so awesome!  It started off the entire evening with such energy and really set the tone for an unforgettable night.”
Cara had one more favorite memory to add: “Sean sang “I Swear” by All-4-One to me towards the end of the night- it was so sweet!”

Featured Vendors:

Kenny Kim and Liv DeHaan for Kenny Kim Photography (pics), The Peninsula Chicago (ceremony&reception), Blu Couture Wedding Films (video), Anne Malcolm from Tying the Knot (wedding coordinator), Mira Couture (bridal salon), Paloma Blanca (gown designer), Jimmy Choo (bride’s shoes), Salvatore Ferragamo (groom’s shoes), Alexa from Zazu Salon and Day Spa (hair), Stylisted (makeup), Kloeckner Preferred Flowers (floral), Arlen Music Productions’ Entourage Band (band), Windy City Limo (transportation)
Can’t get enough Real Weddings? Check out Annie+Christopher’s gorgeous wedding at Ravenswood Event Center or Vicky+Tony’s Salvatore’s bash. Head over to and browse our gallery of Windy City nuptials!