Creating The Perfect Proposal: Stories & Tips From The Experts

Hint: Forward this to your BFF or Boyfriend!
Written by
Laura Cross

It's that time of year! And no, we're not just talking about the holidays ... it's engagement season!! Deciding when and how to plan a proposal is never easy, and regardless of whether you're thinking of going big, small or somewhere in between, creating a memory that lasts a lifetime is the most important feat of them all. You, of course, want every single thing to be perfect and we want to help you do that. There's no wrong way to propose but we've gathered stories and tips from a few of our industry experts who've seen - and experienced - it all.

Hire a photographer to capture the proposal. Or tell your future fiance that you planned a photoshoot for fun so they will be dressed and ready to be photographed. ~ Jeannine Marie Photography

Don’t make it perfect, but make it meaningful to her. She will be telling this story millions of times over - make it so that she cries every time she tells it. ~ Anna Mazumdar, Style-Architects Weddings & Events

Dress up in clothes that make you feel and look good to create the perfect proposal. Propose in a place where it is least expected. Go somewhere unique and exciting, like the 100th floor of a skyscraper where "Marry Me" is spelled out in lights. Propose when she least expects it. Have it planned where family is there to surprise your loved ones and be there to celebrate with you. Love is in the air! ~ Vivian Bernick, Milbern Clothing Co.

Choose a location and/or date that is meaningful to you two as a couple to make the occasion extra special! ~ Mandy Brower, The Dashery

Keep families close by. Although my family was far away, my now husband thought of a great way for them to have a front-row seat to the proposal. ~ Anna Mazumdar, Style-Architects Weddings & Events

Make sure someone is there to document it (or set up a secret camera) because you will want those photos for the rest of your lives. ~ Chelsea Barns, Friar Tux

Don’t cut what you say short. Take your time and make your speech personal and intimate. What my husband said during his proposal is something that I have kept to myself which makes it feel so much more special. It’s a special time in your life that is very intimate and personal, and your fiance will remember your words for a lifetime (even if she doesn’t share them with people). ~ Anna Mazumdar, Style-Architects Weddings & Events

Make the proposal really personalized to who you are as a couple. Proposing in a public setting might seem grandiose, but if that is not true to your love story, then do something more simple. And hire a photographer to capture the moment. Those photos will be something you will cherish. ~ Sarah Trotter, Lasting Impressions Weddings

A perfect proposal includes roses - lots of red roses and rose petals! The more roses, the bigger wow factor and you're on your way to a YES!!! ~ Candace Holmstadt, 651 Studio Floral Design

Make it a complete surprise. I am a nosy nelly and I’m not great with secrets. Usually, I catch on to something but to my surprise my husband was giving me hints for about a week before and I had no idea. ~ Anna Mazumdar, Style-Architects Weddings & Events

My Engagement Story: "After quarantine, like most people, we were ready to get out and travel! Along with Max's family, we chartered a catamaran and sailed the British Virgin Islands. Back story: Max always told me that he would never propose on vacation. We had taken many vacations since saying this, so, needless to say, I never saw it coming! Back to the main story: At the beginning of the trip, Max showed me a funny tweet, "This is our year ... [long pause] ... the Vikings are going to the Super Bowl." [Insert eye-roll!] Max continued to say that to me throughout the trip while also giving loving hugs and looking deep into my eyes. I saw right through his silly words! We spent the last day of our trip at a well-known island bar called “Soggy Dollar” on the beach of Jost Van Dyke. After sipping down our first Pain Killer, Soggy Dollar’s signature drink, we started up another competitive and sandy game of spike ball with Max’s brothers. Halfway through, Rachelle, Max's mom, said, "You should go rinse off. You are getting sand all over me." She knew what was coming and knew I would want to look good! Once back on the beach and taking another sip of our Pain Killers, Max took me into an embracing hug and said, "This is going to be our year!” Thinking it was just another silly Vikings joke, I broke free from the hug. Max grabbed me again and got down on one knee. Max's family was on the trip with us while my family watched the proposal from Soggy Dollar's 24-hour live webcam overlooking the beach. My parents tuned in from their home in Champlin, Minnesota, and my brother broadcasted it to the 9th-grade English class he was teaching in Chaska, Minnesota. Turns out Max tipped everyone off before the trip to the date and time. I was 100% surprised! Looking back at that day, there were so many clues that could have given it away but it was perfect and I wouldn’t change a thing. Definitely a story that we will be telling for a long time!" ~ Anna Mazumdar, Style-Architects Weddings & Events

Include others in on the surprise, whether it is restaurant employees, a driver or wedding industry vendors - we love helping to execute proposals and creating a magical moment! ~ Jeannine Marie Photography