Ali and Kyle
How We Met: Kyle and Ali met via an online dating site in February of 2011. After a few months of limited communication, the two decided to meet at a local bar, Kirkwood, while she was out with one of her new co-workers. When Kyle arrived to the bar, they shared stories and laughs over a Blueberry fishbowl (classy, right?!). Ali’s co-worker saw the instant connection and decided to let the two share the evening alone to get to know one another.
Throughout the night, Kyle constantly warned Ali of his less-than welcoming dog, Riley. He told her she was timid, didn’t like girls, and barked at strangers. After a few hours, Ali decided she wanted to meet this little beast, so they made a pit-stop at his apartment.
As Kyle and Ali entered the apartment there was silence. They wandered into the living room…still silent. After a few minutes, they heard the clinking of a dog chain creeping down the hall. There was Riley in all of her sleepy glory with a welcoming tail wag that would put a smile on any dog lover’s face. Without hesitation or concern, she hoped up on the couch and rested herself between Ali and Kyle. It was love at first sight between Ali and Riley…almost as if Riley knew.
After a few months of dating, Kyle asked Ali if he could call her his girlfriend. Out of sheer excitement that she said yes, he proceeded to throw back the entire bottle of her favorite wine that he gave to Ali that evening. Needless to say, Kyle wasn’t feeling too well the next day and was nervous Ali would change her mind about him. To keep it short and sweet, they ended up moving in together after 6 months (low standards or was she impressed with his ability to throw back an entire bottle of fine wine? We may never know.)
How He Asked: In early winter of 2014, Kyle and Ali set off on a quick 4-day vacation to Miami Beach. After allowing Ali to sleep next to her engagement ring for 6 weeks – Kyle decided now was the time. The surprise was set for Sunday, November 9th.
The two spent the day exploring South Beach in the rain, relocated to a nicer hotel right off the ocean, and Kyle prepared to pop the question. The two set off for a oversized steak dinner, when finally the rain let up (for the first time that day!) just 5 minutes before dinner ended. The two jumped into a cab toward downtown Miami. They were dropped off at a Hilton where Kyle guided Ali through a winding hallway where they popped out the back of the hotel to a private marina. Kyle pointed at a small double-decker boat and said, “I’m taking you on a private tour of the city.” Ali was both anxious and excited that, for the first time ever, Kyle surprised her without having her figure it out.
Of course, Ali started getting hopeful that this was “the time!” After all, how often do the two go on trips like this?
About an hour into their tour, Kyle was still chatting up the captain about Chicago, architecture, and the weather. Ali started to think, “maybe I shouldn’t get too excited.” As the boat began to pass Mark Cuban’s gazillion dollar yacht, Kyle insisted on heading down to the main deck to get a closer look. The two proceeded down to the first level…and that’s when Kyle started his speech and changed their lives. No longer did he just want to talk about getting married, but he wanted to call Ali his wife, his forever. Without skipping a beat, Ali said yes.
As the tour concluded and the two grabbed a car back to their hotel. The rain started pouring down again.