In May of 2018, I was on a vacation in Cabo with one of my best friends, Brian Klein. Brian had recently broken up with his girlfriend; and we had planned this last minute "guys trip" a few weeks before. Having been to Cabo a few times, it would be a perfect place to break him into the single life again. Knowing that Brian had been out of the game for a while...I had committed to being his “wingman” for the weekend. On our first day we noticed two cute girls having drinks by themselves at the beach club next to our resort. After some convincing, Brian agreed to get a table and I began to come up with a plan to meet these two girls. The plan was basic – we would send them tequila shots, they would come thank us and I’d get the conversation going from there. But any good wingman knows you have to have a game plan of “who’s taking which girl”. Both of them looked good in their bathing suits; one of them was quite tanned and the other more fair-skinned. BUT, the fair-skinned girl was wearing a wide-brimmed “Martha Stewart” looking hat that prevented us from getting any idea of what her face looked like. Committed to being a good wingman, I told Brian: “I’ll take the one with the hat, we have no idea what’s going on under there”. He agreed and we ordered the tequila. When the waiter delivered the shots their reaction was not the one we were expecting nor wanted. They barely raised their glasses in our direction, drank the tequila and proceeded to ignore us. You would’ve thought that was the 97th time two guys had sent them shots on the beach that week. Brian (annoyed and a little embarrassed) said “well what the hell do we do now hot-shot?”. I had talked up my “wingman game plan” the weeks leading up to the trip and this was not the start I had planned in my mind. I’ll admit I was a little shocked they hadn’t given us more of an “in” after the tequila. I also knew I couldn’t let this be the initial direction for Brian’s confidence as a newly single man… I calmly said “time for Plan B”. Scrambling my brain for a new plan; I noticed a cornhole set just outside the ropes of the beach club. I convinced Brian that we should go play just the two of us. It would be obvious that we were missing two players and surely they would come join us. Knowing we could very easily fail again; I justified my case by saying…”if they don’t come play cornhole with us, then they don’t have personalities anyway”. After about 2 turns each, the fair-skinned girl in the big hat (who you all know as Jac) came running up with a big grin on her face and said, “we’ll play you guys for the next round of shots”; so I invited her to throw from my end (sending the tanned one down to Brian’s end). Relieved my “plan” had worked, I had hardly noticed how attractive Jac was. Turns out she was wearing the hat to protect her face from a sunburn she got the day before. Although she was burnt, I found her to be stunning and immediately fell in love with her fun-loving personality. That night we took the girls out for dinner and essentially hung out the rest of the weekend just the 4 of us. On the last night we were having a final farewell drink at their hotel bar when a feeling came over me that I now know was fear of losing the connection I felt with Jac. I could feel the word-vomit overcoming my actions and I asked her if she would consider flying to Dallas for a weekend to visit. “You can meet my new puppy, Kirby” I said. A month later, Jac visited me in Dallas (and met Kirby for the first time). Jac and I did long-distance for 2.5 years, got trapped in a tiny apartment together during COVID, then moved to a city where we knew no one so we could finally be together. I never imagined myself doing any of those things for a girl, let alone one from Nova Scotia, Canada. Our story wasn’t an easy one, but I’d do it all over again. Because when you know – you know. - Jon

Ever since we moved to Colorado in 2020, one of our favourite things to do together is to take weekend trips to the mountains. Last April, we took what I thought was an “impromptu” ski trip to Steamboat, Colorado for closing ski weekend. We drove up late on Thursday night with the plan to work remote on Friday and maybe squeeze in some afternoon skiing. I ended up having a super busy workday and around 6:30 suggested that Jon go enjoy the hot tub while I wrapped up. What I didn’t realize was apparently once Jon got to the hot tub he made a panicked call to his brother Josh wondering if he should still go through with his plan to propose given how stressed I was all day. Jon got back to the Airbnb and I quickly got ready to go. Jon tried handing me a drink for the road but I was set on that first patio sip. We parked by the river downtown and Jon suggested that we take Kirby for a walk since it was so nice out. At this point I had a terrible workday and all I could think about was sitting down on a patio and ordering a cocktail before sunset. I could not understand why he was so adamant about wanting to take Kirby for a walk first. Anyone who knows Kirby understands how much he HATES walks. There was still some snow on the ground so I thought fine, Kirby can roll around for two seconds and we can be on our way. During our “walk” Jon asked that we set my phone up to take a timer photo to send to our parents. Seemed like a bit of an odd request from him but then on top of that he said “let’s make it a video instead and take stills from it”. At this point I was fed up and basically said “no that makes no sense”, still somehow completely unaware of what he was trying to do (get a video of our proposal which was about to happen). I ended up leaning my phone up against the top of a bridge post for a timer photo by the river and ran to get in frame. I was so focused on smiling for the photo I didn’t even look at Jon who was kneeling on one knee while also wrangling Kirby into the photo. I heard “Jac” and looked down and basically blacked out from shock. “Is this really happening?”, “How did Jon possibly pick out such a nice ring without my help?” and “Did I almost just micro-manage my way out of my own proposal?!” all went through my head. I immediately started crying and am not even sure what I said except for YES. I would have never thought Jon would be able to surprise me yet despite all the odds against him, it turned out to be my favourite surprise yet. - Jacqueline soon-to-be Buckley