J&R | San Francisco Cable Car Surprise Proposal at Powell & Hyde

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February 24, 2019

J&R’s proposal was so well thought out, meticulously planned, and perfectly executed. It was also a special experience for us — it was the first time Annie and I have split up to be several miles apart for a proposal shoot, and it was the first time I’ve actually appeared in (read: photobombed) a set of proposal photos. This San Francisco cable car surprise proposal is definitely one we won’t be forgetting any time soon!

The plan was for J&R to take the trolley one way and spend a little bit of time at Market St so that a few friends could get set up with “will you marry me” signs, and then he’d propose on the way back. For the actual proposal moment, the plan was for Annie to be on the street to take a photo of the whole scene, and I’d be on the cable car next to them to capture some close-ups, especially of her reaction.

In the morning, as they hopped onto the cable car for their outbound trip, Annie was in place nearby and snapped a couple of sneaky photos of the two of them. After their trolley departed the station, the four friends with signs came out from hiding inside a coffeeshop, lined up on the side of the cable car route, and awaited the couple’s return.

Meanwhile, at the Market St end of the cable car line, I waited for them to arrive. The line there was much longer than expected, so after a brief walk around the area, J&R got in line to head back. In order to get a seat next to them, I played the part of a random tourist and got in line immediately behind them, then browsed Facebook on my phone for the next hour to look like a normal, bored person waiting in line. In reality, I was afraid I might blow my cover due to my excitement for what was coming up!

After a short cable car ride that felt like ages, we approached the destination at Powell & Hyde. R looked up and saw the first of the four signs — “WILL” — and she started to realize what was happening. Next up were “YOU” and “MARRY,” and as “ME” came into view, J knelt down (on the edge of the moving trolley!) and showed her the ring. They were met with congratulations and applause from everyone: their fellow cable car passengers, the conductor, their friends, and even random passers-by. The amount of happiness and excitement that was in the air can only really be described by photos, so please take a look below and join me in congratulating J&R!