The Ultimate Engagement Guide on How To Plan a Wedding Proposal
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The Ultimate Engagement Guide to Planning a Wedding Proposal

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1. Get Mentally Ready for Marriage

“Before you plan a proposal, make sure you’re both prepared for the commitment that is marriage. This is a big step and while you might feel ready, it could be a different case with your partner. Make sure you both are on the same page and that there isn’t anything that could possibly be a problem in the future. While it’s impossible to control what life throws at you, try to make sure there isn’t too much going on so that you both can enjoy the moment once it comes. Discuss what a marriage would mean for you both and what your goals for the future are.” -Melanie Eubanks, Lemon Drops Weddings & Events

“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

2. Choosing the Ring

“Go undercover. Ask friends and family for input, or casually bring up the topic of jewelry preferences in conversation. If you’re unsure, consider a placeholder ring for the proposal and shop for the final ring together.” -Arron McNeile, McNeile Photography

3. Consider How You Want to Propose

“There is a mindset that a proposal needs to be a surprise but, talking about it with your partner to ensure the moment is a special one for you both is important as well. Get some insight into what they would like and think about who they are as a person. While your significant other may be introverted, they may want family and friends there to celebrate. Don’t assume and take the initiative to ask.” -Melanie Eubanks, Lemon Drops Weddings & Events

“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 they cross 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

“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

“When planning the perfect proposal, the most important part isn’t really all of the fluff. It’s making choices that feel like you and your honey! Whether that means you pop the question during the Taylor Swift tour, on the back of a stunning vintage convertible, in your own backyard, or go epic and do it on the rooftop of a hotel…the best part is when you can look back and say, ‘That was so us.’” -Shannon Dewitt, Dewitt for Love Photography

“Maybe it’s a little old-fashioned, but 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. 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

“Start by paying close attention to your partner’s tastes. What’s their favorite restaurant? Do they prefer intimate moments or grand gestures? Consider your shared interests and experiences to craft a proposal that’s uniquely you. -Arron McNeile, McNeile Photography

“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 partner’s 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

“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

McNeile Photography Tampa Engagement Proposal Photograper

McNeile Photography | Whitehurst Gallery

4. Hire a Professional Wedding Planner

“Depending on how intricate the proposal is, it might be a good idea to enlist the aid of friends, family, or an event planner. Not only does this show that you care about family/friends being a part of your new lives together it also gives you a support system to go to and talk about so you don’t have to keep the secret alone. Enlisting their aid can give you perspectives that you wouldn’t have thought about on your own. Just make sure they can keep a secret and lie on the spot if needed. We had a bride run into one of her friends at the hotel where she was about to be proposed to. Luckily, her friend was quick on her feet and utilized the fact that there was a wedding going on that day and said she was attending. She even went with the wedding guests up to the rooftop but veered away once out of sight.” -Melanie Eubanks, Lemon Drops Weddings & Events

“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, 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

“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

“Plan early! Unless you are looking for something very casual, make sure you begin planning at least a few weeks out! Especially if you plan to hire a photographer to capture the moment, have a planning company set up something spectacular, or if you plan to rent a vehicle or event space for a celebration afterward! If you’re planning to set up something epic, consider hiring a professional planning company. After all, you already have a job! Pulling off an incredible proposal is theirs! ” -Shannon Dewitt, Dewitt for Love Photography

5. Hire a Professional Photographer/Videographer

“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

“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

“Find a photographer who not only has captured a surprise proposal before but can help your game plan. Your photographer should help suggest locations that photograph really well, and they are experts at nailing down the timing so that you get optimal light that’ll be the most flattering for you and your partner. Communication is also key with your photographer. Consider coming up with a cue, like a long embrace with your partner, to signal that you’re about to drop down on a knee so that your photographer can get closer and be there to get all the wonderful emotions of the moment. It’s a brief moment with weeks of planning behind it, so make sure you’re comfortable with your vendor team!” -Eddy Almaguer, Eddy Almaguer Photography

“Hiring a photographer for your proposal is a decision that enhances the entire proposal in countless ways. It goes beyond just capturing the moment, it transforms a fleeting instant into a timeless memory. A professional photographer brings not only technical expertise but also an artistic eye, ensuring that the emotions, beauty, and authenticity of the moment are beautifully preserved. They can offer creative ideas, help plan logistics, and provide a sense of calm during what can be a nerve-wracking moment. Moreover, these photos become keepsakes that can be shared with loved ones and cherished for generations, serving as a visual reminder of the love and commitment shared on that special day that started it all! Trust me, your fiancé will thank you!” -Mary Nieman, Mary Anna Photography

“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

“This is the perfect opportunity to get professional photos of a memorable moment in your life starting together. Not only will your now fiancé be excited about the moment, but they will be excited to have pictures to remember this moment forever as well as share and announce the news to others. 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 can also help you (if needed) with location, best lighting/time, and they know where to hide, how to pose, how to capture the perfect angles, etc. If you are wondering how do you hire a photographer to capture this moment without giving away the secret, there are a few ways to do this and your photographer should be able to help you with the plan. ” -Amber McWhorter, Amber McWhorter Photography

“There are a lot of expenses when it comes to planning weddings but, if it’s in the budget ahead of time, consider hiring a photographer for the big moment. Most people have a photo or two depending on if family and friends were around to record the moment, but that doesn’t mean the quality will be there. If remembering the proposal is important to you and your partner, we would recommend hiring a photographer for a few hours to capture the big ‘Yes!’ moment and even take some fun photos afterward. This could also be a good way to build a repertoire with a wedding photographer for the next big moment!” -Melanie Eubanks, Lemon Drops Weddings & Events

“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

“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 with 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

6. Favorite Tampa Bay Proposal Spots

“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

“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

“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

“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

“Think about your shared history. Maybe it’s the coffee shop where you had your first date or a scenic park where you love to take long walks. The more personal the location, the more sentimental the moment.” -Arron McNeile, McNeile 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, 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

“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

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

7. Plan What You’re Going to Say

“Whether the setting is casual and intimate, or public and staged, practice what you are going to say leading up to the big question. Even if you’re an expert at thinking on the spot, get a general idea of what you want to say and repeat it over to yourself so that your nerves don’t get the best of you and you forget. It doesn’t have to be repeated verbatim, but having major points to hit will help take some pressure off.” -Melanie Eubanks, Lemon Drops Weddings & Events

“Make It personal! Include little touches that are unique to your relationship. Recreate your first date, bring up funny shared memories, or write a heartfelt letter expressing your love. Jot down your feelings and what you want to say during the proposal. Practice it out loud so you can convey your emotions clearly in the heat of the moment. It’s okay if you forget everything, a lot of folks do! Just speak from your heart! ” -Arron McNeile, McNeile Photography

8. The Day of the Proposal

“If you want the proposal to be a complete surprise, don’t do a lot of things out of the ordinary that could raise suspicions. If you plan on proposing at the beach but that isn’t normally something you guys do, throw your partner off the trail by taking up going to the beach more frequently. Make it a weekly or biweekly date to visit a beach and take a walk or have a picnic. Save the location of the proposal for that date but make it a habit so they think it’s just another date. That also goes for if you know your significant other would like to look their best for the event. If they would want their nails done or be dressed to the nines, take note of their nail and salon schedule.” –Melanie Eubanks, Lemon Drops Weddings & Events

“Plan the entire day meticulously. Start with breakfast in bed, a surprise lunch, and lead up to the proposal with activities you both love. Think about the small details that can make these moments extra special.” -Arron McNeile, McNeile Photography

“One of the important things you may want to consider when planning a proposal is time of day! If it’s your dream to propose at sunset, make sure you look up the sunset time, and plan for before that time, about 15-30 minutes at least before the official sunset time. Why? Because when the sun sets, it means it’s gone. The light fades very quickly, so if you have someone taking professional photos or photos with a phone, it may become too dark out if you start right at sunset, and something happens to delay it a bit! Remember, this is a surprise, so your soon-to-be fiancé may not understand why it’s so important to be somewhere at a certain time.” -Shannon Dewitt, Dewitt for Love 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. 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

“Stay cool when plans go awry. Be prepared for unexpected twists. If the weather isn’t ideal or a planned activity gets canceled, stay calm and find a creative workaround to ensure the proposal goes smoothly.” -Arron McNeile, McNeile Photography

“Make it extra! Consider some cool ways that you can make this moment extra special! You could rent a classic car to drive you two to the celebration dinner or party you have planned afterward! You could have lots of your favorite photos printed of the two of you and framed all around you! There could be beautiful lighting and hundreds of roses…the sky is the limit!” -Shannon Dewitt, Dewitt for Love Photography

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

Mary Anna Photography Tampa Engagement Proposal Photographer

9. Plan a Post-Engagement Celebration

“Do you want to enjoy the moment, just the two of you, after you’ve popped the question? Do you want to invite family and friends to celebrate with dinner or a party? Don’t stop planning at just the proposal. Think about what you guys will do after. Do something special to mark the occasion, but don’t leave it at the last minute to decide. It will show that you really took the time to think things through.” -Melanie Eubanks, Lemon Drops Weddings & Events

“I like it 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 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

“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

10. 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

About the Author

Anna Coats

Marry Me Tampa Bay editor Anna Coats created Marry Me Tampa Bay in 2012 to showcase the area’s best local weddings and vendors. She has been featured as a wedding expert on the national talk show Daytime, Fox13, ABC Action News, Great Day Tampa Bay, and Bay News 9 (now Spectrum).

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