Ally and Connor

How We Met

Rewind to Summer 2013. I was looking to relocate to Winter Park, FL for a new job and was having the hardest time finding a place to live. My stepmom suggested checking out Craigslist ads. There it was. “Tenants wanted. Must be willing to live in a creative environment as I make a living as a music engineer. If interested please call…”. I was definitely curious. There were photos of a house that seemed pretty cute, so we immediately googled the name and phone number listed. Connor’s Facebook and LinkedIn profiles appeared.

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If you know me, you know I’m an internet sleuth–so we did some serious stalking and decided he was normal enough for me to call and schedule a tour. I drove up a few days later, we met, and I signed a lease to live with 4 boys and 1 other girl in a house that was being renovated into a recording studio. So wild. I moved my stuff in and suddenly life felt like an episode of ‘The Real World’ with a dash of ‘New Girl’. Two or three weeks into me living there and we had a serious spark. Considering we were already living together, you could say our relationship took the “accelerated” course LOL. We fell in love fast and hard. Dating my landlord/roommate was definitely a risk, but the best risk I’ve ever taken. Thanks, Craigslist!

Ally and Connor's Engagement in Orlando, FL

How He Asked

I still don’t have the words to describe the day…so I’m gonna hand it over to my hubby-to-be…

From Connor: It was a Sunday morning and something hit me… I asked myself, “You want to marry Ally Skye, don’t you Connor?” The answer was of course “118% yes”. So I thought, “well…what are you waiting for?” I packed my bags, got in my car, and drove to Ft. Myers to talk with her dad. Our best friends live there too and Ally was out of town, so we were able to play it off as if I was just visiting them. Two hours of great convo with her pops and I got the green light…as long as I followed one rule (sorry, that’s between him and me). It was instant planning from there. I always knew I wanted to do something epic for the proposal. It’s just my style, it’s her’s too.

I started calling all the family and friends that had to be there. I wanted to do it as soon as possible but realized–uh oh–I don’t have the ring yet. By the way, I always knew I would design my fiancé’s ring myself. So step two was hit the drawing board. The ring had to be her style but just as much mine. I researched for days, snuck onto her Pinterest board, her Instagram, and consulted with her friends. I knew what she DIDN’T want more than what she did, that’s all I needed. Something really important to me in the design process was that the ring had to incorporate the number 18. To keep a long story short, the number 18 means a lot to my family and me. It’s tattooed on my dad, my brother, it’s the only number I’ll wear on my back when I play hockey, and I literally named my business after it (Studio 18).

What is the meaning behind ’18’? That’s worth a whole essay, but I’ll give you a short answer here. 1 represents logic, being grounded, the fastest route from point A to point B. 8 represents the infinite amount of possibilities, it represents love and creativity. They are opposites yet need each other to function, much like the two halves of our brains, much like Ally and I’s relationship. The 1 and 8 represent the unity of us. So I draw the design, I find the ring maker (that’s a heck of a story in and of itself). Sketches back and forth between them for weeks and we finally have it ready. They 3D printed it, cast it, built it, set the diamond and sapphires (my birthstone, her request) all within 2 days of the proposal.

The day is coming up and things are getting hectic. I’m driving around Winter Park scoping out Air B&B’s to have the party. My mom and I settled for something that would barely work, only to find out hours later my mother found this house of dreams on a lake. It couldn’t be more perfect. The morning of, Ally wakes up to go shopping with her best friend, Brynn, for our trip to Italy (her sister is getting married there soon, it’s going to be AMAZING). I was at a “work event” all afternoon with my friend Ross (Brynn’s boyfriend) and when the girls got back to our apartment they started getting ready for their BFF photo shoot I got Ally for her birthday (also all part of the master plan). I figured if I disguised the moment as a photo shoot I could have cameras there AND it would ensure she’d have on her best outfit + nails done (that’s important fellas, make sure her nails are done).

It’s 2:30, I’ve got the whole family at the lake house waiting for the limo to pick us up and bring us to the photo shoot location where they would be hiding and jump out after the proposal. The limo was 30 mins late and the band didn’t have the PA system yet (there’s a band involved too, we’ll get to that in a minute). Basically, we were cutting it close. Finally, the limo arrives, we pop champagne and head on over. We arrive with about 20 minutes to spare at a local bar M lounge.

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I need to tell you about M Lounge. This place has been around for about a year in Orlando, is by far the nicest bar/lounge, and not enough people know about it! It’s a vintage car gallery/museum with an incredible lounge. I knew it would be PERFECT for pics. My two camera guys meet us there. I have to give a shoutout to our photographer, Kadeem aka Arrogant Watcher, and videographer, David Daudin of MYTO Weddings. These guys have been my friends for years and I couldn’t have picked a better team.

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My dad, Kadeem and I stage the shots, then everyone heads to the back room for the pre-party. Ally arrives, looking stunning as always, and Kadeem asks her change into her “more elegant” outfit for the first shots. Ally thinks David is just doing “behind the scenes” video for Kadeem. Brynn’s boyfriend Ross and I arrive (unexpected) because Kadeem’s “next client” canceled and he invited us to hang out/join in on some shots if the girls would let us.

I was already dressed up nice and spiffy and Ally didn’t suspect anything because she was under the impression I came from a work event. In reality, I was hanging with the family all day. We did some group shots, then Kadeem isolated Ally and I. I held her hands and looked her in the eyes. I started going off the script I wrote earlier..and to be honest I started to black out. I think we both did. Whatever I said was from the heart, and before I knew it I was down on one knee.

We were both in tears. Kadeem came over to take the photo and then I held my hand up and yelled “1…2…3… Hit It!”

At which point the band (who moments before snuck out behind us on the floor mid proposal) started playing “Crazy In Love” by Beyoncé and Jay-Z. This band, by the way, is the same crew I worked with and lived with for years at the studio I operate. These guys are like my second family, and they’re AMAZING musicians. Our families started to file out from behind the room one by one.

Ally could barely handle it, in fact, people were taking bets on whether or not she would faint. I knew she’d do just fine and enjoy every second of it. She did. We danced and drank for 30 minutes before I looked at my watch and said “Babe! We gotta get going, we’ve got a dinner reservation!”

We went outside to get in the “Uber” but nope, there was the limo. Surprise upon surprise and they kept getting better. I opened up the limo door for Ally and inside were all her best friends. They came in from Miami, Atlanta, Philadelphia, Brooklyn, Gainesville, Jacksonville, Sarasota..all over. The house was only 10 minutes away but we partied in the limo for at least 45, and it was a party!

We pulled up to the house, Ally had no clue where we were, we get out and there were about another 40 people waiting for us cheering. Ally cried again. So did I. It was amazing. The party was next level: catered, DJ, we even had a surprise bagpiper (my stepdad Dave always like to spice things up one way or the other.)

There were so many highlights of the night, one of the great ones was my 45 minute off the cusp toast. Yeah, I know, that sounds like an eternity but I was able to tell a story about almost everyone at the party and it meant the world to both me and them for reminiscing on what makes our lives so special. Ally and I getting engaged was, of course, the main theme of the evening, but so much of our relationship and lives has to do with the people who were standing in that room, I couldn’t let that go unnoted. We slept at the house that night and woke up to a wonderful brunch hosted by Ally’s dad and her stepmom.

The weekend was magical. We’re still on cloud nine and I couldn’t be happier with what matters most to me…how happy she was, is, and will be until the day we die.

Our Video

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Special Thanks

David Daudin
Videographer
Kadeem Cobham
Photographer