Jayleen & Kailer | Golden Gate Bridge Double Surprise Proposal


Jayleen is a Puerto Rican, queer, non-binary badass. Kailer is a proud trans man and a veteran. And in a small, rural area of Pennsylvania that doesn’t really embrace queer folks, the universe conspired to bring them together.

I was honored when Jayleen and Kailer came to me with the idea of a “just because” couple’s portrait session for their trip to San Francisco, marking a new chapter after a very challenging year in their lives. Soon afterwards, I heard from each of them, separately, that actually, they wanted to surprise the other with a proposal. Double surprise proposal! What??? So exciting. We started the session with just a few portraits, and the disappearing-and-reappearing Golden Gate Bridge. And then…

I’ll let them take it from here, in their own words:

Kailer’s hidden agenda—Jayleen and I had made a pact that we wouldn’t get engaged until our lives were in a place that would allow for us to truly celebrate this special moment. We wanted it to be its own celebration, not tainted by all of the external negative energies we had battled throughout the previous year. We are both divorced. After my first marriage, I didn’t think I would ever want to get married again but then I met Jayleen. She turned my world upside down! I knew from our first “date” that I was going to marry her one day. Fast forward a year, and I finally bought her ring. I waited to get the ring because I knew as soon as I had it, waiting to give it to her was going to be very difficult for me. And, I was right. As soon as the package arrived in the mail, I wanted to get down on one knee and ask her to be my partner for the rest of my life. But I was bound by our agreement. Then we decided that we wanted to take a trip and celebrate the fact that we made it through some hard shit. We decided on San Francisco, and I instantly thought this would be the perfect place to ask. However, I wanted it to be captured on camera. I wanted to be able to see this memory for years to come. So, I asked Jayleen if she wanted to do a random photo shoot in San Francisco. She loved the idea—she’s always game for these types of things! Little did she know, this was the perfect cover story to get new outfits as well as provide a reason to get up before the sun the day after our arrival. Together we found Anna and decided she would be great for documenting this occasion. Once Anna responded to our seriously last minute request for a photo shoot, I emailed her separately and told her that it was going to be a surprise proposal. I was so nervous that Jayleen was going to see the email or the ring as I packed it, but I pulled it off. Even after plane delays and not getting to bed until 1am only to get up at 4am to get ready, I made it happen. I got down on one knee in front of the Golden Gate Bridge and asked my twin flame, my honey bee, mi reina, my home to spend the rest of my life with me. And she said YES!!

Jayleen’s poetic surprise—I was all about this trip and just traveling given the inability to do so this past year—we’re both adventurous spirits so this was the perfect opportunity to reignite that flame. The more I thought about it, I just knew this would be the perfect backdrop for a proposal. See, Kailer and I were previously married to other people. I knew that when I married again, I would do it differently, including the engagement. I’m all about breaking down the rigid boxes that so often confine us—I wanted to take ownership of my own story and lead with my heart. This moment would be a reflection of me, our love, and all of the ways in which we broke all the rules. I started planning. Initially, I thought about doing something very intimate during the camping portion of our trip. I shared this idea with my mom, and she suggested the photo shoot would be a great opportunity to have the moment documented. I was slightly hesitant because I know Kailer doesn’t typically like the spotlight, yet I was definitely pulled toward this. How wonderful to have this documented for years to come? Plus, we could spend the rest of the time celebrating our love and another reason to take more squishy, love drunk selfies in San Francisco doing touristy things! This was clearly a win. So, I went for it. I emailed Anna and told her I wanted to propose to Kailer during the photo shoot. She was all about it! Seriously, no hesitation, which is another reason why she was the perfect person for this job. I knew I wanted to read Kailer a poem I had written that contained my proposal. Kailer is my muse—I’m always writing him poems, and he always tells me how much he loves my words. I had written it the year prior, as well as bought the ring, because I just knew in my heart this was meant to be. He is my person. I edited the poem to reflect the setting, folded it up, and hid it, along with the ring, in my pocket. Now, I was hella anxious and slightly paranoid that it was going to fall out or get snagged by TSA in the airport! I love surprises and really wanted this to remain a surprise. Luckily, despite all of the hiccups during our long travel day and lack of sleep, I managed to hold onto everything. And so did Anna—if you want someone who is really good at secrets, she’s your person. I had no idea that Kailer had also reached out to her, and she definitely didn’t let on. She had given me a cue for when I would read my poem and then propose. However, before I even got to that point, Kailer was all of a sudden in front of me, on one knee, and asking me for forever. The whole thing was perfect. After I said yes, it was my turn. I pulled out my poem, got on one knee and set the next chapter of our lives in motion. The look on his face was just priceless and beautiful. We were both so over the moon, filled to the brim with joy.

Our story is our favorite. This double surprise proposal certainly lived up to the theme of our relationship so far—the universe is on our side.

Even their rings were both tree themed, with Kailer’s ring having a bark texture, and Jayleen’s ring a thin branch with leaves. They had not discussed them beforehand!

This was truly such a delight.

Congratulations, Jayleen & Kailer! Thank you for inviting me to be a part of your story.

Anna Wu is a wedding and portrait photographer based in San Francisco. She strongly believes in affirming LGBTQ+ love and is constantly learning and working to be a better ally. She has become quite adept at hiding in unexpected spots during surprise proposals. Contact her to inquire about your own proposal plans.