Tara and Ryan

Engagement Proposal Ideas in Buckingham Fountain, Illinois

How We Met

Tara: We met on Monday, May 13, 2013, at O’Donovan’s bar in Chicago. I was graduating from law school the following Sunday and just started working at Chicago Sport and Social part-time two weeks prior. I was dreading this Monday night shift because I spent the whole weekend celebrating the end of law school finals and was running late to hand out free t-shirts to the softball teams that came to O’Donovans.

Finally about three hours into my shift, a guy (Joe Laraia, best man) came to the back bar and asked for t-shirts. After making small talk for a few minutes, he asked me to come and have a drink with his friends, but I politely declined. About 10 minutes later, he came back and asked for a few more t-shirts, and I gave him the t-shirts.

Another 15 minutes later, a different guy (Ryan) came to sit by the bar and asked for t-shirts. I asked him what team he played for, and it was the same team that already received free t-shirts. I was confused and said I already gave them a bunch of t-shirts! Ryan quickly replied that he really came to hit on her. We talked for about 45 minutes, and Ryan asked me if I wanted a drink and to meet his friends. I hung out with Ryan and his friends for the rest of the night, and then he asked for my number. We had our first date on June 4, 2013!

Marriage Proposal Ideas in Buckingham Fountain, Illinois

how he asked

Ryan: It started with a three month process picking the most important piece of jewelry I will ever choose. I already knew where I was going to ask the love of my life to marry me. In the very beginning of our relationship Tara told me her favorite monument in Chicago was Buckingham Fountain. I always had it in the back of my mind that when the day came, I was going to propose there. That was the easy part. Once I had the ring and destination figured out the initial plan on how to get Tara to Buckingham Fountain was challenging because I wanted it to be a surprise. Months before I proposed Tara and I have had multiple conversations on getting married so I had to be clever.

Where to Propose in Buckingham Fountain, Illinois

I thought the best way to distract Tara to fall for my surprise was to set up a fake double date with her friend, Linda, and her boyfriend. I asked her to send out a group text and request this double date at Cindy’s rooftop, which is just across Michigan Avenue from Buckingham Fountain. Everything went according to plan and the fake date was set up! I even thought it was a great idea to higher a photographer to capture the moment. I waited until a few days before the big day and nonchalantly mentioned we should get downtown early and check out the fountain. She was all for it which was a sigh of relief. The entire process of getting Tara to the fountain went so smooth I was getting even more excited for the day.

On September 24th, I was filled with joy and excitement. Ok, I was also a little nervous but the nerves didn’t settle in until minutes before. Once I knew the photographer was at the site I wasted no time. I had coins ready in my pocket to throw in the fountain. Once Tara turned to throw the coin I took the ring out of my pocket and got on my knee. What do you know, she said yes!!

Tara: A few weeks before the proposal, one of my girlfriends texted Ryan and I and asked if we wanted to double date at Cindy’s Rooftop in Chicago. I texted Ryan asking if he wanted to go and he said of course! Unbeknownst to me he had asked my friend to set up this fake double date. My favorite Chicago landmark is Buckingham Fountain and Ryan had not been there since he was a child. Ryan asked if I wanted to go to Buckingham Fountain before the double date since the restaurant was across the street. I should have known right then but I still had no idea.

The day of the proposal I thought it was just another night out and spent the day running errands. I got ready and Ryan and I took the train downtown. He did not seem nervous or jittery at all. We took a cab to Grant Park near Buckingham Fountain and when we got out of the cab Ryan asked if we could take a little walk. We walked through the gardens and then walked toward the fountain. Ryan then asked for a quick bathroom stop and as we were walking toward the Fountain he asked me if I still wanted my sunglasses on. I should have been totally clued in at this point but still had no suspicions.

Ryan and I walked to the front of the fountain and he took two coins out of his pocket and said we should make a wish into the fountain. As soon as we had thrown the coins he said a charming and romantic line, got down on one knee, and asked me to marry him!

I was so in shock that I just kept laughing and Ryan had to ask if that was a yes. I said YES! It took me a solid 90 seconds to finally look at the ring because I was so in shock! It was stunning and perfect. Ryan hired a photographer to capture this unbelievable moment and in many of them I am just laughing the entire time. The proposal was absolutely perfect and I could not have planned it any better myself! I am so happy it was all captured and am so in love with the photographs and Ryan.

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