A Proposal Hidden Inside an Anniversary Road Trip
For five years, Kelsey (she/her) and Chelsea returned to the same stretches of the California coastline, turning favourite towns and scenic lookouts into places that belonged to them. So when it came time to propose, there was never going to be a better setting than the roads they’d travelled together time and time again.
What Kelsey thought was another anniversary road trip quickly became something much bigger. Chelsea had spent nearly a year planning every detail, from a vintage red Mustang and a breathtaking floral installation to having their dream photographer waiting nearby.
How did your story begin?
We originally met on good old Hinge! We went on a few dates, decided to just be friends, and after a few months of friendship, we fell in love. The rest is history.
How did you plan the proposal?
Kelsey: Chelsea had always been very clear that she wanted to be the one to propose, and I was more than happy to patiently and eagerly wait for that day.
We used to live in San Diego, and our favourite tradition was taking an annual road trip up the California coast. Every year we revisited the same small coastal towns, and over time those places became sacred to us. After we moved to Denver, Colorado, Chelsea suggested we fly back to California for our five year anniversary to continue our tradition. What I didn’t know was that she had actually been planning the proposal for nearly a year.
She secretly reached out to my best friend, who also happens to be an incredibly talented florist, and together they brought her vision to life. She also booked my dream photographer, Anna Captured, whose work I had admired for years.
On our anniversary, we spent the day visiting our favourite spots around Carmel by the Sea before Chelsea surprised me with a vintage red Mustang convertible for a drive along the California coastline. Singing Taylor Swift with the top down, she casually suggested we stop for a few photos. Instead, I found a beautiful floral installation created by my best friend, with Anna hidden nearby to capture every moment. At Bixby Bridge, Chelsea got down on one knee and asked me to spend forever with her.
How did Chelsea keep the ring a surprise?
Chelsea wanted to make sure it was a complete surprise, so she devised a plan with some friends to get an idea of my ring preferences without me knowing. About six months before, a close friend texted me saying she wanted to start ring shopping for her girlfriend, already had an appointment scheduled at a local jeweller, and wanted my help choosing the perfect ring.
Little did I know that the appointment was really just a ploy to get my ring size and an idea of what I liked. From there, Chelsea started customising my ring for the big day!
What has your engagement meant to both of you?
Although I had always known that Chelsea was my person and that we would spend our lives together, our engagement still marked a significant milestone in our relationship.
For years, we hoped that my family, who hold deeply religious beliefs and do not accept our relationship, might eventually come around. Chelsea especially wanted the opportunity to build a relationship with them before we took this next step.
After more than five years together, we realised we didn’t want to put our future on hold waiting for anyone else’s approval. It wasn’t just a proposal. It was a commitment to continue building the life we wanted and celebrate our love exactly as it is.
Nothing changed about how much we love each other, but it changed how we viewed our future. We stopped waiting and started celebrating it.
Why was it important to have your proposal photographed?
We always knew that we wanted this special moment to be captured. Chelsea took note of a photographer whose work I’d gushed over many times. She secretly booked Anna well in advance and coordinated her travel to Big Sur so she could capture the proposal for us.
What does wedding planning look like so far?
So far, we’re just enjoying our time being fiancées. We’re not in a rush, so we haven’t started contacting vendors or doing any major wedding planning. I am, however, building vision boards for the big day because I can’t help myself!
What do you dream your wedding day will look and feel like?
We dream of our wedding day being intimate and surrounded by our chosen family and the people who genuinely celebrate our love. The vision is vineyard, château, French villa.
Photography by Anna Captured
