In 2011, we published a proposal story about a guy who built a Starbucks. In the woods. From scratch. Shane and Mikaela’s first date had been at a Starbucks, so when it came time to propose he rebuilt the whole thing under the trees and got her out there on the pretense of a photo shoot.
We have been collecting these for 15 years and they have never once gotten old. The surprise proposal on a secret cliffside in Big Sur that photographer Lynn Lewis had to keep quiet for weeks. The couple who spotted a lake on Instagram while planning a trip to Switzerland, drove five hours out of their way to see it, and came home engaged. And then there is Crystal and Persis, whose proposal and wedding happened on the same day in LA, because one of them planned an entire wedding without the other catching on!
Every one of those started with someone sitting down and typing out what happened. Which is exactly why we said yes to this one.
The contest: “When You Said Yes”
Our friends at Lovebird are running When You Said Yes, a proposal story contest open through the end of September, and the structure is the smart part. Instead of handing one prize to whoever had the most cinematic sunset, a judging panel is picking a winner in each of four categories:
- Most Creative Proposal. The Starbucks-in-the-woods tier. Scavenger hunts, custom builds, a year of planning in service of a 90-second question.
- The Sweetest Proposal. No production value required. Kitchen floor, ring in a coffee cup, both of you crying before either of you says anything.
- Proposal Plan Gone Wrong. More on this one below, because it is the good one.
- Most Memorable Reaction. The scream. The knees. The person who said “are you serious” 11 times before saying yes.
Each category winner takes home $500, and one grand prize winner gets $2,500. Entries close September 30, 2026 at 11:45 p.m. ET, and the terms and conditions are linked right on the entry form.
About that “Proposal Plan Gone Wrong” category
This is the one that deserves the most entries and will probably get the fewest, because the reflex is to file your story under “doesn’t count” the second something goes sideways.
Consider what actually qualifies. The rain. The ring box that would not open. The waiter arriving mid-sentence. The dog. The friend who was supposed to be crouched in the bushes with a camera and got locked in a restaurant bathroom instead. The proposal that had to happen four hours early in a parking lot because somebody’s sister could not keep a secret.
Those are the stories people ask you to retell at the rehearsal dinner, the ones your friends have heard four times and still request, and Lovebird built a whole category around them with $500 attached. Go enter that one.
How to write one that lands
The panel is going to read a lot of these. A few things that will help:
Start in the middle. Not “we met in 2019.” Start at the moment the plan started going right, or wrong, and backfill from there.
One strange specific detail beats five lovely ones. Skip “it was a beautiful sunset.” Go with the fact that he had been carrying the ring in his jacket pocket for nine days, and you had borrowed that jacket twice.
Write what you were thinking, not just what happened. The few seconds where you already knew and were pretending not to know are the best few seconds in any proposal story.
Do not clean it up. The version where nothing went wrong is always the more boring version.
And one more thing, whether you enter or not.
Most proposal stories live in exactly two places: your memory, and a group text nobody is ever going to scroll back far enough to find. The details go first. What the light was doing. What you said right before you said yes. Sit down and write the whole thing out once, properly, while you still have all of it. Your future self will be grateful, and so will whoever ends up reading it out loud at your wedding.
Who’s behind it
Lovebird is a digital-first platform for wedding guest communication, which is a tidy way of describing the part of planning that quietly eats your evenings: getting the details out to everyone, and getting the details back from everyone.
It is digital top to bottom. Save the dates and invitations, wedding websites, meal selections, RSVP tracking, guest list management, and timely announcements for when plans shift, which they will. The point is that it is one system instead of six, so the spreadsheet, the group chat, and the cards you are still waiting on stop being three separate problems in three separate places. Learn more about all that Lovebird does →
They come from a company with a long track record and award-winning technology, which matters more than it sounds like it does when the thing you are trusting it with is your entire guest list eight weeks out.
How to Enter
Head to lovebird.com/proposals, pick your category, and write it the way you would tell a friend over coffee. Deadline is September 30, 2026 at 11:45 p.m. ET.
This post is sponsored by Lovebird. All content and opinions are that of GWS. Thank you for supporting the brands that help keep Green Wedding Shoes running.
