The Ultimate Engagement Guide for Planning the Perfect Proposal

1. How to Pop the Question

“Preparation is key! First off, make sure you are ready to get married: financially, emotionally, psychologically, etc. There are all types of marriage counselors, and they are all very helpful in asking the right questions to each of you before the life change. Asking someone to marry you is essentially taking a back seat to your own well-being and caring for another as much or more than yourself. You must be ready! Then, when it's time to propose, make it a huge surprise!” – Brandon Wheeler, Gulf Beach Weddings

“When planning the proposal, pay attention to potential hints your significant other has been throwing your way and what they might like for this moment. If there were no hints dropped, no worries! Write down things you think of when it crosses your head, and if you can add in small details that would mean a lot to them, then do it! You want to make sure this proposal is a direct reflection of them and that it is planned with lots of intentionalities. For example, we had a client get a cookie cake that said “She said yes!” because he asked her to be his girlfriend in the form of a cookie cake a few years prior.” -Delaney Driver, Wilder Mind Events

“Proposals do take some planning, but try to make them as natural as possible! They will come across as more authentic and meaningful if you are yourself. You'll most likely be a little nervous, so it's important to have details already in place: select a spot (check the weather if it'll be outside!), and have something in mind for right after, whether it's a surprise photo shoot or a gathering of friends and family.” -April Sherwin, NOVA 535

“Make the experience personal by incorporating elements unique to your personality and relationship. This can mean partaking in a favorite activity, enjoying a favorite food, or including a personal decorative element. Enjoy hiking trails? Recall a memorable first date meal? Obsessed with Disney? Tie those details into your proposal, and it's bound to be more special and memorable than a generic ‘fancy dinner' or ‘holiday ring box under the tree.' Also consider documenting the experience with a secret photographer or videographer, because just like a wedding, the experience flies by in a blur, and without someone to capture the moment, your memory may get fuzzy due to emotions running high!” -Christi Winsor, Winsor Event Studio

“Maybe it's a little old-fashioned, but I think it's exceptionally meaningful to reach out to your partner's parents and let them know your intention of marriage. Especially if your partner is a ‘Daddy's girl,' knowing that dad approves of you is a big deal. It also keeps your partner's parents in the loop, and I believe it sets you up to start your marriage off on the right foot in your future parent-in-law's eyes. I also think it's important to propose in a way that's meaningful to your partner as opposed to doing what ‘everyone else does.' If your partner is a quiet, shy person, they may not want to be proposed to in front of a large crowd. If family is super important to them, maybe it's best to propose in front of family at Thanksgiving or Christmas. If your partner is obsessed with Disney, and maybe you're not so much, perhaps bite the bullet and propose at Disney!” -Bonnie Newman, Mars and the Moon Films

Downtown Tampa Sparkman Wharf Engagement Session Carrie Wildes Photography

Carrie Wildes Photography

“Carry the ring. The ‘perfect time' may not be the best time (perhaps there was an argument heading out to the beach, or the dog misbehaved just before you left, or you got stuck in traffic and missed the sunset. I personally carried the ring for a few weeks until the timing was right, then down on one knee. Also, wear loose clothing for the ring box. It seems like a simple task, but the box is bigger than you think and might give away the surprise. -Brandon Wheeler, Gulf Beach Weddings

“When officially popping the question, think about having some kind of ‘keepsake' from this special moment. A custom ringbox, engraved wine glass, etc. will become something that will sit on a shelf for future generations to see.” -Staci Mandikas, owner, UNIQUE Weddings + Events

“Everyone and every couple are different, so choose something that fits your personality, not what social media pressures you to do. If your partner doesn't like being the center of attention, proposing during football halftime probably isn't the right move. The proposal should really be special to the couple, so the location is important. Maybe choose where you met, where you had your first date, a favorite vacation spot, or propose while on a dream vacation. Documenting the event is also preferred, so after you know where and when you should book a photographer. That's also a great way to establish a relationship with a photographer that you may want for your wedding.” -Karen Cerboni, EventFull Weddings

“Do something personal to the two of you; include a favorite date night location or a place with special meaning for both of you. Include favorite foods or adult beverages. Do your research and always have a Plan B. Proposing on the beach might sound like a great idea, but there's a lot to consider. You have to deal with changes in the weather. Champagne is a must, but you might not be able to have glasses (champagne, glasses, or candles) on the beach. Pick some of your special songs to set the mood. While roses and candles are highly recommended, if the person you propose to has a favorite flower, go with those! You're also on display and might not have any privacy. You're also out in the wide-open, so hiding a photographer, music, or even family can be challenging.” -Tammy Waterman, Special Moments Event Planning

“I always recommend doing the proposal on a random day! You are more likely to get wonderful surprised reactions if you steer clear of holidays, birthdays, anniversaries, etc. Make sure your partner is wearing a nice outfit! They will forever hold a grudge if they are sporting loungewear in the photos.” -Heather Lorenz, The Birchwood

“When it comes to the perfect proposal, our biggest suggestion is to keep this special to you and your partners relationship. Incorporating elements that have been important in your love story brings more sentiment and romance to this special moment! Along with that, the element of surprise is always a huge plus.” -Jessica Ralph, Parties A'La Carte

“Before you decide what to do for your engagement, find out what’s important to the person you are about to propose to. Many clients that I have asked have said that having their family there is important to them. Have the ring ready and make sure you have asked for permission if that is a requirement. Get family or friends involved! They may have some great ideas for you. Have fun and be present! You love this person, and hopefully, they are not expecting perfection. And if all of this sounds like you can’t handle it…hire a planner!” -Paulina Bartnicka, Amici's Catered Cuisine

2. Favorite Tampa Bay Proposal Spots

“I think a proposal is such an intimate question and really a fork in the road, and the location should be very intimate. My favorite is just in your living room, where it is just you and your spouse. Because through life, many times, it is just you and your spouse. Your life partner.” -Michele Renee Zerda, Michele Renee the Studio

“The best proposal ‘spot' is somewhere that is meaningful to you as the couple. Maybe it's your first date spot, where you realized you wanted to spend your life with this person, or a previous vacation destination. You'll want somewhere semi-private and quieter to make sure your partner can hear you and so you can hear their response! I love somewhere with a view as well!” -April Sherwin, NOVA 535

“Clearwater Beach! It has been America’s number one beach for many years in a row. There are plenty of places to park and many opportunities for surprises. I believe the beach is perfect for couples who love nature and the beach. It is extremely budget-friendly, which will leave you some budget for the perfect ring.” -Paulina Bartnicka, Amici's Catered Cuisine

“There are several hotels with rooftop terraces along the gulf and the bay with spectacular views and sunsets. They also give you a tremendous indoor backup plan if you need one and can help you through details like dinner or additional services. Hyatt Regency Clearwater Beach, and The Wyndham Clearwater Beach all have great rooftop locations. The Clearwater Aquarium has some beautiful options that can include dolphins. The Grand Hyatt Tampa has a private beach location that can offer you some better options than a public beach. Wedding planners have all the resources you need and can develop creative ideas for planning a proposal.” -Tammy Waterman, Special Moments Event Planning

Groom on Bended Knee | Surprise Engagement Proposal at the Hyatt Regency Clearwater Beach | Clearwater Wedding Photographer Djamel Photography

Bachelor-Inspired Surprise Wedding Proposal | Hyatt Regency Clearwater Beach | Djamel Photography | Special Moments Event Planning

“One great spot for a proposal is North Straub Park in Downtown St. Pete! All of the trees, grass, winding sidewalks, and waterfront views make for a gorgeous background in photos. Once you put a ring on it, you can head across the street to The Canopy's rooftop where you can surprise your partner with her family and friends!” -Heather Lorenz, The Birchwood

“It depends on the way you plan the surprise proposal. I have had couples ‘book a session,' and then in the middle of it, the photographer gives the cue for the proposal, and SURPRISE! If it is completely a secret, meaning there is no actual photography session planned, choose a location that is somewhere not too isolated. If it is just the couple and then someone casually off in the distance, it may seem odd, but if it is a place that typically has other people, it will seem less noticeable. With these reasons in mind, I think the beach or a park is a perfect place for a proposal. I wouldn't choose a very packed beach or park, but one that has some people.” -Amber McWhorter, Amber McWhorter Photography

“Anywhere on the beach in the Tampa Bay Area or Panhandle just prior to sunset. Florida sunsets are literally world-renowned. If you choose a weekday/weeknight, you will have more privacy. Don't make it obvious. If you've never gone hiking to a mountain cabin, or fine-dining on the beach, or on an unplanned Jamaican vacation, it tends to be a bit out of the ordinary and expected. Keep it light and spontaneous.” -Brandon Wheeler, Gulf Beach Weddings

“Decide if you want it to be private, in a public spot, or if you want friends and family around. Whatever you decide, make sure you have some alone time after you propose. There is an overwhelming flood of emotions, and it's a lot to process. To best soak it in, have a dinner or something similar planned so that you two can enjoy one another's company and can reflect on the special moment that just took place.” -Delaney Driver, Wilder Mind Events

“The best proposal spot is somewhere close to you and your partner! Whether it's cozy in your home, your favorite coffee shop, or the place you had your first date, it makes it much more special when there is a meaning behind it! Small and intimate is my advice to soon-to-be engaged couples! You will really be able to soak in that special moment together!” -Kelci Ziconi, Kelci Leigh Events

3. Hire a Professional Photographer/Videographer to Capture Your Engagement

“Similar to a wedding, the proposal experience flies by in a blur, and without someone to capture the moment, your memory may get fuzzy due to emotions running high! To avoid raising suspicion, many photographers and videographers offer ‘secret coverage' where they document the proposal from afar, allowing for more privacy.” – Christi Winsor, Winsor Event Studio

“Capturing video of such a moment can be such an amazing heirloom to have! The key difference between a friend using an iPhone and a professional videographer is audio and video quality. As professional videographers, we can hide a microphone in your shirt and be able to capture high-quality audio of your partner's reaction and yours as well! If you end up hiring the same videographer to capture your wedding, we can even use the footage and audio from the proposal in the storyline of your wedding film. Imagine showing your future children and grandchildren that film!” -Bonnie Newman, Mars and the Moon Films

“If you want to take your proposal to the next level, definitely hire a professional photographer. I LOVE photographing proposals, and besides actually taking the photos, we help with the planning of it, in terms of the best time of day at your specific location and how to capture that amazing moment! You can also use these images for your wedding Save-the-Date and website, which is such an awesome way to share it with friends and family!” -Carrie Wildes, Carrie Wildes Photography

“Hire a professional photographer for your proposal because they will be able to provide you with high-resolution images that you can keep forever. They know where to hide, how to pose, how to capture the perfect angles, etc. If you just let your friend document it, your photos probably are on a phone, not high-quality, and could deteriorate over the years, leaving you with not the best photos of this important milestone in your life.” -Amber McWhorter, Amber McWhorter Photography

“Hire a photography and videographer team! You put in so much effort for this moment and for it to look amazing; having someone there to capture it is a memory that you can have forever. After they say yes, you can have a mini shoot of you two, the ring, and whatever else; think of it as a mini engagement shoot!” -Delaney Driver, Wilder Mind Events

Mars and the Moon Films

“All photographers absolutely love love, it's in their DNA! But they are also great at putting their emotions aside and getting down to business, which is capturing that one perfect moment! Friends and family are great to celebrate with afterward, but they may be too emotional and excited to focus on the task at hand. Leave it to someone who has been there and done it countless times before!” -April Sherwin, NOVA 535

“Hiring a professional photographer and videographer gives you someone who might be less conspicuous than a friend or family member, and you can be sure they won't miss a shot! This is not a moment you want to trust to your smartphone.” – Tammy Waterman, Special Moments Event Planning

“Make it a photo finish. One of my greatest personal regrets is not capturing the moment by a third party ‘in the moment. My wife's family wanted pictures in the act (of professional quality) and/or to be involved in the surprise. Something to consider!” -Brandon Wheeler, Gulf Beach Weddings

“A fun element of surprise is to include your family or close friends in your proposal plans! Some of my favorite proposal sessions were when the groom would plan to propose during a family photo session or invite friends to a picnic and propose right before their arrival. Not only do you get great reaction photos, but you also have a mini celebration afterward.” – Joy Hmielewski, Joyelan Photography

“You need to hire a professional photographer and videographer for the engagement because these are the milestones in your life that you want to remember forever. You don’t want some shaky cell phone video to look at in 20 years!” -Paulina Bartnicka, Amici's Catered Cuisine

4. Hire a Professional Wedding Planner

“Don't be afraid to plan far in advance and to invest in this special day. Planning a proposal can be one of the most exciting and nerve-wracking things you might ever do. Keep it a secret In order to make it the ‘perfect' proposal. To keep it a secret, I would start by hiring a professional to plan your proposal. When you hire our team, we can handle most of the vendor communication and planning so that there are NO slip-ups on your end. It takes out a huge chunk of emails and phone calls so that you can fly under the radar and your partner won't suspect a thing.” -Delaney Driver, Wilder Mind Events

“First things first, hire a planner! We take the stress out of planning your proposal, so all you have to do is show up with the ring and pop the question. All of our proposals are personalized to what your fiancé will like and want. There is a lot of pressure on the person asking to make a production of the event to capture all the details, have a photographer, have a videographer, and to have something Pinterest-worthy for the ‘GRAM! Your fiancé will want to brag to everyone! That’s where we come in to make sure all is accomplished without you having to do any of the work. We book the venue, permit, and location for you. We book the photographer, videographer, and florist for you. We discuss the plan of execution, help with a cover story to throw off any clues, figure out how to get your future fiancé to the location, and provide ideas for the celebration afterward. No two couples are alike; no two proposals are alike. Hire a planner to take the stress off your shoulders, and we’ll create a proposal you both will not forget.” -Melanie Barker, Elope Tampa Bay

“Look for an event planner who offers proposal services. Our team has been asked to arrange for quite a few proposals. If you are not hiring an event planner, find an accomplice to help set everything up. You will not have time that day to get everything laid out on your own.” -Tammy Waterman, Special Moments Event Planning

5. Favorite Locations to Celebrate After Your Engagement

“We love when couples enjoy a celebration with friends and family immediately after the proposal, so consider planning a group function to coincide with your engagement. This may be a secret gathering of friends at your home when you return from your proposal experience, or it could be a restaurant reservation that serves as an excuse to get all dressed up and out of the house, aiding in your proposal surprise.” -Christi Winsor, Winsor Event Studio

“The Canopy at the Birchwood is the perfect spot to celebrate after the engagement! Since it's a rooftop lounge, you can hide friends and family members up there without being seen from a distance. Once the elevator doors open, everyone can yell “Surprise!” -Heather Lorenz, The Birchwood

“My favorite locations to celebrate an engagement are somewhere where the couple can enjoy and celebrate their moments together. If you propose on the beach or at a park, you can plan a little surprise picnic with some champagne. If you aren't feeling a picnic vibe, you can make reservations at a place that you both love. It is important to include moments and locations that you will hold close to you forever.” -Amber McWhorter, Amber McWhorter Photography

“I like when the celebration is immediately after the proposal, and the excitement is in overdrive. If you are proposing on the beach, consider a trendy beach picnic or beachfront restaurant. If you are a little more formal, choose a restaurant that has a private room or space that can accommodate your guest list. If the two of you are wine lovers, a wine bar cocktail party is an intimate setting and great for socializing. The key is to consider what your fiance' would like and who you are as a couple to make it a memorable occasion. Having your celebration photographed is a great add-on, so you have photos with all your friends and family.” -Karen Cerboni, EventFull Weddings

“My favorite place to celebrate after an engagement would be at Tommy’s Tiki Bar at the Hilton Clearwater Beach. You can have some cocktails to celebrate while having your feet in the sand.” -Paulina Bartnicka, Amici's Catered Cuisine

6. If You Think a Proposal is Coming

“Don’t ask too many questions. If you’re asked to dress for a night out, do it! Check your nails. Invest in a manicure more often than usual. Relax, go with the flow and enjoy!” -Tammy Waterman, Special Moments Event Planning

Outdoor Terrace Wedding Feasting Table at St. Pete Wedding Venue The Birchwood | Intimate Micro Wedding Elopement COVID Styled Shoot | Fall Autumn Wedding Inspiration | Hotel Terrace Reception with Canopy String Lights Orange Copper Wedding Table Linens | Gold Beaded Glass Chargers with Napkin and Menu Card and Gold Flatware | Wedding Centerpiece with Orange White and Peach Roses

Shauna and Jordon Photography | The Birchwood

Quotes have been lightly edited for clarity and brevity.