Olivia and Jay

How We Met

In September of 2016, I had just officially joined my first dating app. I ran to auditions in the morning and ended up sitting on my couch scrolling through the app feeling less than hopeful about my potential matches. I knew instinctively that while dating apps can be right for some people, this wasn’t going to be the way for me. To shake off the energy of my perceived dating shortcomings, I threw on some old sweats, smeared sunscreen all over my face and bounded out the door to get a hike in before sunset. I had just peaked the overly trendy “Runyon Canyon” in LA and was jogging down the dirt path heading back down when a girl from my morning audition stopped me to chat. I didn’t know her well but we made small talk and wished each other luck, she then introduced me to her hiking buddy, Jay, who was an absurdly handsome British man. I–for no real reason–assumed they were dating and said it was nice to meet him as I started to make my way off on my hiking adventure. He stopped me in my tracks with “you have really beautiful eyes”. I paused awkwardly, still unsure of how exactly these two knew each other.

Engagement Proposal Ideas in Alcazar Boutique Hotel in Palm Springs

I sputtered something about- “you are really beautiful people” and ran away. Apparently, they were not dating and Jay luckily quizzed her on what little she knew about me so he could track me down later and try to connect. He found me on Facebook (which I haven’t used in years) and found that one of our very few mutual friends was a lovely woman that he (and I) trusted implicitly. He had her gauge my interest– “that cute hiking guy IS single? Yes, I’d like to meet him again!” He texted (major eye roll from me because I was hoping for an old-fashioned phone call). He didn’t even introduce himself via text, just asked me out. I told him that “I give my number out all the time” so he should be a little more specific on who he is. I learned later this was somewhat terrifying for him as he hadn’t asked anyone out in quite some time and just getting the courage to text was almost too much for him. Luckily, I doubled back with “a little soon for sarcasm?” And we were off and running. Literally. Our first few months of dating were full of visits back to Runyon and exploring other hikes all over LA and even in Hawaii. We found the best way to get to know each other with no pressure was to hike alongside one another. Two years later and I still feel closest to him every time we hit the trails.

Wedding Proposal Ideas in Alcazar Boutique Hotel in Palm Springs

how they asked

I wasn’t shy in sharing with Jay my pre-emptive thoughts on our dream wedding. We had bounced some ideas around on ideal places and had both agreed that “one day” we would like to get married in Palm Springs. It was the location of our first real vacation together and was just two hours away from where we lived in LA. It was the perfect getaway without the hassle of planning a big trip. Jay announced that we were due for a Palm Springs trip in August (just a couple weeks shy of our 2 year anniversary).

I was a little weary about an August trip- the temps were over 100 for the whole week! But it had been a bit since we had a romantic getaway so I was up for the adventure. We drove out and began to check into the very hotel I had mentioned wanting to scout as a potential wedding venue- The Alcazar. It was quiet boutique hotel nestled into the main strip of Palm Springs and it is absolutely beautiful. My suspicions that something was up were heightened when the suite we checked into was larger than the one-bedroom apartment that we share in LA. Jay then asked if he could treat me to a massage the next afternoon.

At this point, I was pretty confident we were about to get engaged but was really trying not to “expect it” and set myself up for disappointment just in case he was just trying to be really romantic but didn’t actually propose this trip. Luckily, when I returned back to the hotel after my spa-day it all became clear. He was standing outside in his navy blue suit and when he saw me his eyes welled up and I knew for sure it was happening. He asked if he could blindfold me and his hands were shaking as he did. He slowly led me into the courtyard of the hotel where weddings take place. He began telling me how much he loved me and a whole bunch of sweet things that neither one of us can specifically remember. I helped him take off the blindfold as I just couldn’t wait to see his cute face again. When I could see again I realized he had created a “wedding aisle” complete with hundreds of tea light candles and red rose petals. He cried. I cried.

He got down on one knee. I said, “yes, yes, yes, yes”!!! And kissed his face as fast as I could. He put the ring on and we both could hardly stop laughing and crying the happiest tears. My friend, Kate Moore, then hopped out of the bushes and it turns out that she had photographed the whole thing! We jumped right into mini-photoshoot as I kept saying over and over- we are engaged! I couldn’t believe that all he had planned for us. He then whisked me away to a beautiful five-star restaurant around the corner. The hostess congratulated us as soon as we walked in and we celebrated with champagne toasts when we sat down.

When it came time for dessert we both decided that it was enough of a fancy night and we wanted to make sure we were always just “us” married or not, so instead of a five-star desert we went to the local frozen yogurt shop and made our favorite mixes which I then dropped all over the yogurt shop floor- I couldn’t help it I was still shaking from excitement! I made up a silly song that I still sing to him anytime I’m trying to be cute- “love of my life, one day I’m going to be your wife!” Now that “one day” is a real day and the countdown is on! I can’t wait to marry this thoughtful, generous, kind-hearted man.

Special Thanks

Kate Moore
 | Photographer