Surprise Pittsburgh Proposal | Roberto Clemente Bridge

I have quite literally never had to keep myself from ruining a surprise as much as I did for this proposal.

Chelsea became a fast friend of mine in 2016 when I crashed a trip she and her friends were taking to Vegas. We hit it off quickly and were soon inseparable. We celebrated birthdays together, we drank mimosas together at tailgates, we’ve bonded over Jell-O shots... yeah we’ve drank a lot together hahah.

So Chelsea and Charles actually began planning their wedding a bit out of order. They each knew that the other person was endgame and that they definitely wanted to be married to each other. So they booked a date at a venue, and then booked me, and then got engaged.

And honestly? This isn’t as uncommon as you might think! With couples having to reschedule and postpone their dates, vendors are booking out much sooner than they used to. So if you’re set on marrying the person you’re with, and they’re equally stoked about it, why not start planning?

Anyway, we had planned for these couples photos to happen when I was in town, knowing that if they were engaged by then, we’d use them as engagement photos. And if not, we would just hide the fact that Chelsea wasn’t wearing a ring. But Charles and I knew what was up.

Chelsea had been texting me alllllll week, super bummed about the fact that she and Charles weren’t engaged yet. Throughout every text message, I had to constantly be like, “It’s okay! No big deal! We’ll still have fun at our session!” … all the while knowing what was being planned. We met up in downtown Pittsburgh for a sunrise session so that there would be fewer cars around. And with a road as busy as the Roberto Clemente Bridge running right through downtown, we had to be extra careful! Thankfully, it was a quiet Sunday morning – perfect for getting engaged.

Eventually the moment came. I gave Charles the “cue,” and he knelt down, asking Chelsea to spend forever with him. Keep scrolling to see her reaction! Spoiler: she said yes.

Are you planning a surprise proposal and don’t know where to begin? Get in touch, as I’d love to help you and capture this moment!