3 Proposal Tips // Sarah + Trey’s Engagement

HIP HIP HOORAY! The planner finally gets engaged!

Here’s the backstory on this long awaited day. In 2020, Sarah and Trey met on Hinge, after Sarah swore she would never go on a dating app. Never say never, right? The two hit it off, and dated for 2 years before Trey popped the question. However, we all know the planner had some tips + suggestions to share.

Trey was so excited, he slipped up and told Sarah the date and location not one, twice, but THRICE. Since he messed up the original plan of a picnic at Centennial Park, Daisy helped him come up with a back up option. That one fell through, too. However, the third time was a charm. Trey completely redeemed himself with the final location.

While Sarah was aware of the date, she didn’t know the full plan. Her hair was curled, make up done, and she was scheduled to meet a couple of friends at 3PM. But then, there was a plot twist. Due to work adventures and clients needing her full attention, Sarah was trapped on calls. Trey was sweating bullets, but our wonderful friend and photographer, Jordan, talked him off the ledge. Sarah tried to cancel with her friends, but they refused. She now knows they were part of the plan!

1.5 hours later, Sarah arrived to meet her friends. They chatted about the wild day, and then Kirbee directed them to the rooftop to share some good news. They sat on the couches, and Trey made his move from the third floor stairs. He got in place behind Sarah, and when she stood for a toast, Trey was on one knee.

Of course, Sarah said, “YES!”

Because Sarah was tardy to the party, they missed their dinner reservations Trey had made at Restoration Hardware. However, he whisked her away to their next stop. Trey had planned a SURPRISE engagement party at Sid Gold’s! Sarah walked into a room full of friends + colleagues and was so shocked! Sarah had no idea, but Trey had created a spreadsheet for people to sign up and contacted people via DMs that he didn’t even know that well. While he let some of the proposal details slip, the engagement party was a complete success. Also, it was Opera night at Sid Gold’s so everyone got to hear some delightful tunes, and after their crew departed, our gang sang some karaoke, too.

Here are 3 tips that will make your proposal stand out!

  1. Propose at a special location. – Find a place that’s important to both of you. Maybe it’s your first date restaurant, your go-to hiking trail, or surprise her on an upcoming trip. Trey knocked it out of the park by getting special permission and planning at Sarah’s favorite spot, Restoration Hardware.
  2. Hire a photographer – This was at the top of Sarah’s list! While it’s not a necessity, having the photographer capture these special moments is a once-in-a-lifetime opportunity. You can reminisce for years to come, and the photos tell the story.
  3. Include her most important people. – Ask her best friends + family to make sure her nails are ready, she’s in proper attire, and even to help get her on location. They know what she likes and doesn’t. If you can pull off a surprise after party like Trey did, she will never forget that day.

If you need assistance planning an epic proposal, contact our team!

Photography: Jordan Roepke Photography