Connor and Morgan

How They Asked

While knowing she was the one was easy, asking her made me more nervous than anything before! Thank God He helped ease my nerves and make everything fall into place. Around July of 2018, we had just come home from a missions trip and we wanted to do some more traveling. She had mentioned a city environment (since we live in FL) around the holidays as she loves the Christmas feel in a big city. I was born in Chicago so I asked her what she thought of going there and we quickly agreed that this would be what we do! With 6 months to save, we hit our budget in timely fashion booking tickets, rental car, fun activities and everything else we wanted to do months before the trip. While she thought we were going to enjoy a great time in the city, I began to plan for another hidden element… our engagement.
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Connor and Morgan's Engagement in Chicago

Like I said before, I knew a long time ago, in fact, I knew when we got home in July. I began asking her girlfriends, seeking advice from my buddies as well and everyone rallied behind my decision. My dad and I, about 4 months before the date I proposed, made reservations at a famous steakhouse in Downtown Chicago. Then I checked to see what time the ice skating rink below the famous “Bean” closed which is where I proposed. Finally, I checked the closing times of the local rooftop bar where I knew we could go after and celebrate.

When it came to ring shopping though, I looked for about 3 months but I just couldn’t find anything that really screamed “Morgan”. I decided to ask her mom to weigh in on the situation and her mom, who also loves Jesus, said she felt God wanted me to be at ease with my decision so I waited and trusted God knew best. It was a month before and I decided to online shop when I found a jeweler by the name of HelloRing and they had this beautiful pear-shaped, art deco style bridal set that screamed Morgan!! I sent the photo to her mom and she immediately approved and as you can guess, within 30 minutes the ring was on it’s way to my house. I only had one more thing to do… 2 weeks later, after Thanksgiving, I asked her Dad out to dinner and we had the most amazing conversation about marriage, love, how to keep marriage alive and healthy but most importantly he offered his blessings and prayers which gave me complete confidence going into the trip.

Traveling with the ring was hard, I had to play a game at airport security where we raced to see who can make it through first (so she didn’t see the ring on the LCD screen lol). By the time we were in Chicago though, things were smooth sailing. My cousin hooked us up with an amazing videographer to come and film the event and all my planning was finalized. From there, we enjoyed visits with family, great pizza, and attractions but when it came time to make our 6 o clock reservation on Sunday the 16th, I made sure we were on time. Both of us enjoyed some of the best food we had ever eaten but I’ll never forget the conversation, the time together and how beautiful she looked.

I knew it was time to leave so we ordered an Uber, entered the ice skating rink and from there, the rest is history! Most of this moment seems blurry due to heightened emotions, big smiles, and overwhelming anticipation but I have a clear image burned into my memory of the moment I put the ring on her finger. I felt a shift in our relationship that has forever changed us in the best way. I knew I had just become engaged to be married to my best friend and honestly the most amazing woman ever. We left the rink and celebrated at Cindy’s Rooftop Bar, which overlooks the ice skating rink, and there we started to make phone calls home to friends a family.

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