Courtney and Ryan

How We Met

Ryan and I met in the most romantic of all places – a bar! I was out with my gal pals for one of our friend’s birthday, when we decided to stop by one of our favorite weekend hangouts, BBC. My roommate at the time had called one of her best friends, Anne, to meet up with us; unfortunately, Anne couldn’t make it, but sent her now-husband, Chris, instead to be her placeholder. Not wanting to be the only dude in a group of chicks, he convinced one of his buddies to go out with him for “just one drink.” When we arrived at BBC, Chris introduced his friend to the group as his “single buddy Ryan.” Being very single myself, I was picking up what Chris was putting down and strategically positioned myself next to Ryan. We chatted the entire night until we realized it was only the two of us left. Ryan texted himself from my phone (his phone had died sometime during the evening – typical Ryan) so he could have my number for when his phone finally worked.

The next morning, I woke up to a text from Ryan (yay!), but all it said was “Unsubscribe” like someone would enter to a spam promotional text. I should mention that to this day, Ryan thinks that’s the funniest thing he’s ever done. After some witty back and forth banter, Ryan then sent me a screenshot for an Uber tab of around $200 from the night before! He informed me that he had Ubered back to his house in the burbs, only to realize he had left his car and house keys with the valet driver at Cirque (where Anne and Chris lived). So he had to drive back into the city, pick up his keys, and drive back to the burbs again, resulting in a very expensive “one drink” night. I think we would both agree it was worth it though!

Later in the week, Ryan asked when he could take me out to dinner. I told him I was really busy not training my dog (Ryan’s pet peeve) and being funemployed (a whole different story entirely), but that I thought I could carve out some time for him. Ryan responded that we could go any day I wanted so long as it was Thursday and that we could eat at a restaurant of my choosing, so long as it was Mexican food or sushi. I chose the sushi place around the corner from my apartment (just in case I needed to make a quick exit). Luckily, it was the best first date ever, and we have been together ever since!

How He Asked

I have an affinity for wine, and because of this, I have always wanted to visit Napa. Fortunately for me, Ryan loves wine and traveling so we decided to take a quick weekend trip to Napa in March. We got there on a Thursday after Ryan insisted no less than 800 times I okayd it with my boss first that I could take off from work (my boss literally couldn’t have cared less but Ryan was persistent).

Once in the wine-region, we did the usual wine tours and tastings and ended the day by having a nice dinner out in Sonoma. We were going on a hot air balloon ride first thing Friday morning, so we turned in early. Around 1 am, I thought I must have drunk a little too much wine because I woke up feeling terrible. Spoiler alert: I had food poisoning and spent the entire night laying on the bathroom floor. I felt awful because (1) food poisoning and (2) we were going to miss the hot air balloon, and I didn’t want to ruin Ryan’s vacation with my illness! Fortunately, I started feeling better later in the day, so we picked up with our afternoon schedule of wineries. If you know anything about Ryan, he’s a planner so it was very natural there was a schedule in place.

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Still feeling a little queasy, I asked Ryan if he would be embarrassed if I wore my Lululemon leggings out to the winery. Being ever so smooth, Ryan gently reminded me that we were going to a nice steakhouse dinner after the winery tours and that I might want to wear something a little nicer. Begrudgingly, I put on real people clothes and some make-up knowing Ryan was right. On our way to a private wine tasting, Ryan kept reiterating that he was so glad I was feeling better. Like SO SO glad. I agreed because not feeling like death was pretty nice.

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We arrived at the winery, which was extremely nice but looked more like just a large house sitting on a small vineyard. Ryan said the tasting was going to be around back out on the patio so I followed his lead, phone in hand ready to take some pictures, trying to muster up the strength to drink wine after being so sick earlier. As we turned the corner, I looked up and saw a woman who looked JUST like my mom. For real, it was her twin. Then I looked over and saw my brother and dad, then Ryan’s parents, then I realized it WAS my mom and literally all of our friends and family were standing there waiting for us! I was in complete shock. Before I could really process everything, Ryan told me the sweetest things I’ve ever heard and asked me to spend forever with him. Ever so casually I said, “OMG YES!”

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Once I hugged every single person I love, Ryan had one final surprise. The “private winery” was actually an Airbnb that Ryan had rented for everyone to stay in for the rest of the weekend. It was the most fun weekend of my life! I can’t wait to spend forever with someone who is so thoughtful and loves me so well. We are so excited for our wedding and January can’t get here soon enough!

Special Thanks

Jen Philips
Photographer