Kaylin and Bryan

how they asked, My perspective:

Since the day I met my sweet Man 11:11 has always been our thing. We look at the clock at 11:11 often and make a wish. This is something I have done since high school.  When I met him I got him into it and it never fails almost every 11:11 he screenshots it , sends it to me and tells me he loves me. It’s crazy how something so small can mean so much. So 11:11 is our time.

Several weeks ago He started planning an event called “suit night.” A tradition he’s started since he’s been an air traffic controller. Everyone dresses up for a night on the town. Guys in suits, the ladies all dolled up. I have been to one before so I believed it right away. The day before 11:11 Bryan came home all excited from work and said 2 of the people going wanted to fly there and show up like rockstars. I am scared of planes and said I would rather not and I would meet them there. Bryan wasn’t having it. He said baby the weather will be perfect. You’re going to be alright. It took some convincing but I said okay! Just an hour before we took off Bryan got a phone call, which was fake, saying that the guys weren’t going to be able to make it to fly to New Orleans. I immediately said perfect we will drive. He again reassured me saying everything is going to be okay and said we will just get the Cessna N5107B which is the smaller plane. It was the plane he had taken me on for our first date.

So just minutes before we left I called my mother and said we are flying to New Orleans for suit night and I’m a nervous wreck, scared , and that I loved her.  Neither of us knowing the real reason of this flight she tried to convince me to not get on plane and just drive and meet them. Bryan wasn’t having it though. He was already doing the checklist for take off and helping me get in the plane safely. The whole flight there I kept asking are we ok and he just kept reassuring me we were going to be fine.

We finally landed at lakefront airport and everything appeared to be normal little did I know the happiest moment of my life was about to happen. He got out of the plane and came to my side where the door seemed to be jammed, lucky for him because believe me this girl was trying to hop out the moment the plane stopped. Once he got me out of the plane he walked me to the middle of the plane. First thing I’m trying to do is take a selfie and send to my mom and best friend that we’ve landed safely. He had other plans though. He grabbed both of my hands and started saying how much he loved me and I thought what are you doing stop playing around we are going to be late for suit night. Then all of a sudden I heard the cracking in his voice, saw the realness in his eyes and felt his hands shaking as he told me again how much he loved me and wanted to spend the rest of his life with me and before I knew it he was down on one knee asking me Kaylin Gail McGregor will you marry me? I immediately said yes!! Then all of a sudden a hidden photographer jumps out taking pictures and bystanders start clapping. I couldn’t believe how much thought and effort he put into it. This sweet man of mine pulled off the most amazing and epic proposal ever. So of course there was no suit night. This special day 11/11 was planned out for weeks to the T for us. We took more photos, had a wonderful dinner at a famous steakhouse (Besh Steak) and enjoyed a wonderful night on the town.




how they asked, His Perspective:

Our first date was a short plane ride to New Orleans for dinner in Cessna N5107B.  This is the plane I did all my training in including my first solo flight.  It only felt right that this airplane be part of my plan.

11:11 has always been our thing. We look at the clock at 11:11 often and make a wish. I always take a screenshot and text it to her. 11:11 is our time, so I wanted to make 11/11 our day.  Several weeks ahead of time, I started planning the event.  I had the perfect ring made, and flew into the Lakefront airport to meet the photographer to plan the day.

A tradition since I began my career as an air traffic controller, was to get together for “suit night.” Everyone dresses up for a night on the town. Guys in suits, the ladies dolled up. I told Kaylin we were flying into New Orleans with a few of the guys from work for “suit night”.  At the last minute I received a planned phone call where the guys cancelled the flying part and it was just the two of us.  I told her they would pick us up when we landed. It took a little convincing, but I got her in the plane and we headed to New Orleans.

Reaching New Orleans, I taxied to the ramp where our photographer was in hiding.  I got out, walked around the plane to help Kaylin out. Voice cracking and shaking nervously, I shared the real reason we flew into New Orleans, dropped on one knee to pop the question.  She said “Yes!”



We took more photos, had a wonderful dinner at a famous steakhouse (Besh Steak) and enjoyed a wonderful night on the town.  The whole thing went down just as planned and Kaylin was completely surprised. I was so relieved that I could finally come clean with all of my fibs!!!




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Special Thanks

Brooke Boyd
Brooke Boyd Photo + Film