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Proposal Planning: Tricks of the Trade

Here, Heather Vaughn, Founder and Owner of The Yes Girls, provides a comprehensive guide exclusively for Heartalytics. Anyone considering I do, tune in…

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It’s feeling like engagement season at Tawkify! There’s been an uptick this Fall in clients asking the big question, making October the ideal Heartalytics issue to discuss the topic for any readers requiring engagement support. Here, Heather Vaughn, Founder and Owner of The Yes Girls, provides a comprehensive guide exclusively for Heartalytics. Anyone considering I do, tune in!

The Do’s

Do Make It Personal: Consider 3 things that your significant other loves and incorporate those elements into the proposal. For example, her favorite flower, a meaningful location for him, an inside joke shared between the two of you displayed creatively…these details beautifies the space while making it about the two of you. When you’re intentional with the proposal details it speaks volumes. It affirms that you know him/her better than anyone.

Expert tip: We have found fiancés absolutely love tangible items they can save as a keepsake from the proposal.

Do Get Photos: This may seem a given these days but even if he/she is an introvert or you don’t know if they would care to have the photos, it’s better that the option is there. Simply because, you can’t redo it! The photographer (and videographer if you can swing it in your budget) can remain hidden so there is no added pressure while capturing the proposal moment. Your future fiancée will appreciate having the photos and/or video as a reminder of your special day for years to come.

Do Allot For Buffer Time: We recommend having 30 minutes of buffer time before the proposal just in case your significant other is running late, parking becomes an issue, or if a vendor needs a little extra time for setting up. It’s much easy to kill time than it is to make up time. Timing is a big indicator something is up because s/he starts to notice you’re acting off or stressing over it which can ruin the surprise.

The Don’ts

Don’t Ruin The Surprise With A Bulky Ring Box: Your jeweler’s ring box is great for safe keeping but if it sticks out when inside your pant or jacket pocket it’s a dead giveaway. Our favorite way to hide the ring on the proposal day is Box Sock—it’s a pocket sock that hides the ring box. The thin ring box is discreet and hides perfectly inside the sock’s pocket so your significant other won’t notice a thing.

Don’t Make It Memorable For Instagram: Make it memorable for your person. While we love our social media tools, when the focus is on what will look awesome for an Instagram photo versus the setting he/she would appreciate, it takes away from the genuine moment. For a more raw and emotional reaction, create a setting the speaks to him/her, not something you’ve seen dozens of times on Instagram and Pinterest. An instagram proposal 10,000 others have copied and re-grammed is a hard don’t.

Don’t Schedule Dinner Before The Proposal: You can use “dinner” or a “double date with friends” as an excuse to get him/her to the proposal location but make sure to propose before dinner versus after dinner. Why? You’re likely going to be a nervous wreck when dinner runs over and the proposal champagne is no longer chilled! The point? It’s hard to gauge how long dinner will be (if you order dessert, for example, or the food takes longer to bring out, etc) and then it can throw off your timeline for the proposal; especially if you have a photographer waiting, or any family and friends involved. Instead, pretend dinner reservations are running late, propose and then enjoy a celebratory dinner after he/she says “yes!”

The Tips

For travel lovers: Incorporating rose petals is a common ask for those popping the question. Instead of the classic red rose petals in the shape of a heart, create something custom. For example, our florist created a large world map entirely out of pink and red rose petals. The couple loved to travel so we had map markers indicating significant memories around the rose petal globe. The final map marker was placed in Dallas, the city he was proposing!

For game lovers: The Yes Girls created a custom life-size crossword puzzle which was a stunning backdrop for the New York proposal. The couple played the crossword game which gave clues/memories from their relationship. The last clue hinted at a very special question, which I’m sure you can guess! View more photos and their proposal story here.

Photo: Sincerely Emelia Photo

For the fairytale, Disney lovers: One of the most dreamy proposal settings was when we brought the romantic floating lanterns scene from Disney’s Tangled to life. The thousands of “floating” lanterns was an installation of hanging lit lanterns. The movie is an animated scene so we pulled from various elements that the couple loved such as the song, the flower selection, and the princess’ sun emblem hand crafted onto a blanket.

This may not be your specific style, but the tip here is to embrace your romantic side. If you don’t have any immediate ideas, ask loved ones, do some research and think hard on what would make your loved one feel most special.


About The Yes Girls: The Yes Girls are the World’s Original Marriage Proposal Planners. The expert team thoughtfully helps you create your dream proposal, all the way up to the moment she says “YES!”

Established in 2008, The Yes Girls have created over 3000 one-of-a-kind experiences from marriage proposals and anniversaries to re-proposals and date nights for their glowing clients! TYG couples love stories have been featured on the Today Show, GQ, ABC News, NY Times, and more.

Heather Vaughn, The Yes Girls

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