Sapaan and Keena

Bride's Proposal in Chicago

How We Met

We matched on an Indian dating app called Dil Mil in March 2015. Both of us were hesitant to use a dating app, but happened to both give it a try at the exact same time and we both swiped right on each other. I lived in San Antonio, Texas and Sapaan lived in San Jose, California. One of the first messages we exchanged was about our favorite basketball teams (The San Antonio Spurs and the Golden State Warriors), who were both gearing up for the NBA playoffs. A fierce basketball rivalry followed. We continued to text each other for several months until I finally planned a trip with my friend to visit San Francisco in October. Sapaan and I spent the weekend together going on a series of double dates with her friends and decided we wanted to keep seeing each other afterwards.

Proposal Ideas Chicago

How They Asked

[Sapaan] The proposal was an absolute surprise. And I’m impressed with myself that I was actually able to keep it a surprise. Planning: I had been thinking about what I could do to for my proposal for a long time. I wanted to incorporate something extremely personal and involve our families. I had an idea of recreating our favorite memories so I interviewed several artists and eventually I hired one with a very fun artistic style. I provided her with several pictures of my favorite memories with Keena and asked her to recreate these with her own artistic style.

Wedding Proposal Ideas in Chicago

After a few weeks I received the final prints and got them framed. My next step was to figure out how I would show these to Keena. I wanted an elegant display of the pictures so I thought of setting these up on easels. I looked for several different locations in Chicago and decided on Maggie Daley Park (where I took Keena iceskating for the first time a year prior). Here is where I needed help, so I recruited my brother, Keena’s sister and her fiancé to help me bring this idea to reality. Both of our families booked flights to Chicago for the weekend without telling Keena. The night prior to the proposal, our siblings helped assemble the easels and coordinated with our photographer, Janet, on logistics. They went to the park in the morning to help set the artwork up at Maggie Daley and quickly handed off to Janet who was stationed near it waiting for Keena and I to approach.

Where to Propose in Chicago

Sapaan was visiting Chicago just before one of his business trips to China, so Keena was unsuspecting of anything unusual. Sapaan had told her that he wanted to have a “chill” relaxing weekend in Chicago before his business trip. On Friday Sapaan booked a couples spa date at Aire Ancient Baths in Chicago and reserved a table at Tao Chicago for dinner. Prior to the trip Sapaan had mentioned to Keena that his best friend (that Keena hadn’t met yet) would be visiting Chicago the same weekend with his fiancé. Sapaan had started a group text message with Keena and his visiting friends to make the story believable (they weren’t actually visiting). Sapaan’s friend texts the group saying he scored 4 free tickets through work to the afternoon show of Hamilton in Chicago on Saturday (an excuse for all of us to get dressed up). Keena had been planning to wear a leopard print dress, and I knew she would hate that she wore it once she realized I was proposing. So I told her how much I hated the dress until she decided to choose another outfit.

On Saturday morning we made plans to meet up with our friends for brunch before “the show”. Because they were visiting from out of town they wanted to do touristy stuff and visit the famous parks in Chicago to see “The Bean” among other things. They called us asking us to meet them in the park before going to lunch. That was my cue to head over to the park. Snow was falling the entire ride over and Keena even told the driver to take us directly to the restaurant instead of going to the park. I insisted that we had to meet my best friend in the park because this was their first time meeting and they wanted to wait there for us. Keena argued that it was snowing and was upset that we were going to walk through the snow. It was extremely cold and snow was hitting us in the face as we walked towards the proposal location. The whole walk she was complaining and she was starting to get into a bad mood. I tried to keep her calm and shield her from the snow until we approached the location.

As we get there I say “So the real reason why I brought you here is because I wanted to show you something”, and that is when she first caught a glimpse of all the artwork placed on easels in the park. She immediately realized what I was about to ask and started crying. I walked her through each of my favorite memories with her and when we got to the last painting (of me proposing to her in Chicago) I asked Keena if she would marry me and continue making these memories with me for the rest of our lives. She said “Yes!”. Afterwards she asked if my friends were even in town, I said “No, that was just to get you here”. Then she asked if we are actually going to Hamilton, I said “No, but I promise I will take you one day.”

After I proposed she joked that she didn’t even have her nails done (a prerequisite that she said she needed done if I were ever to propose). She was also extremely thankful that I made sure she didn’t wear her leopard print dress. I told her that I booked a room for us at The Ritz Carlton Chicago to celebrate our engagement and that we could call our parents when we get to the hotel. At this point we were freezing and could barely feel our fingers. We quickly grabbed all the artwork and called an uber to the hotel. Once we got to the hotel we went straight up to our room, the Ritz Carlton was aware of my proposal plans and had upgraded us to their Water Tower Suite with a phenomenal view of the city.

We entered the front door while our families were hiding in the living room around the corner. As soon as we entered the room they all yelled “Surprise!” and congratulated us with hugs on our engagement. Seeing her family and my family together in Chicago had been a wish of Keena’s ever since she moved there. This was the first time everyone including our siblings were in town. This brought Keena to tears (happy tears). We all celebrated together with drinks and enjoyed the rest of the evening together. Another Chicago bucket list item for Keena was to dine at the world-famous restaurant, Alinea. I managed to get us reservations for dinner and that capped off the final surprise for the weekend. [Keena] It was a complete surprise! I didn’t even have my nails done! I cried, we laughed, our families were there, and it was more perfect than I could have ever imagined.

Special Thanks

Janet D Photography
 | Photographer
Maggie Daley Park
 | Location
Monique Machut
 | Illustrator