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From Women to Men: Tips for the Perfect Proposal

This one is for the MEN! But guys, don’t let the title fool you into thinking, “Here we go again.” I asked a couple women what tips they would give the guys preparing to propose. And I think you will be super surprised to hear what some had to say.

I hope the tips from all these lovely ladies help calm those nerves and give you better clarity into what might mean the most to your girl when it comes to asking her that all-important question. We get it. It’s a big deal. And it’s a scary thing to do. You’re determining the end goal of your relationship with just one question. But I’m not here to help you make your mind up. This is for the guys who already have that part figured out.

This is for the men asking, “How?” and “When?” and “Where?” With all that is going on in the world, it may seem like your proposal plans have been put on hold. Maybe you had a perfect trip or idea in your mind that got canceled when things started to shut down.

But here’s the thing: when it comes to proposals, you’d be surprised about what women really expect from that special moment. I’ll just let my friends speak for themselves…

Ladies: If you could give any tips/ideas/advice to a man trying to plan the perfect proposal for his girl, what would you say?


Personalize your proposal! You are two unique people with your own unique love.

Mikaela

I loved this one. Some guys think they have to give their girl a proposal story that’s different than the usual. But that is easier than you think. There is nothing that can every completely match the relationship between the two of you. Because you’re each your own unique person – with likes, dislikes, hobbies, passions, talents, and character traits all your own – then the blending of the two of you creates a combination that this world has never seen before. You’re like fingerprints! Keep the proposal true to the relationship you both have with one another, and it’s sure to be a story no other woman on earth can tell but her.

Make it sentimental. My husband brought me to a restaurant that was super special to us: first date / I love you / be my girlfriend all happened there, so now it’s the place we went to after we got engaged. Just tie in something that means something to you as a couple. Also, get a secret photographer or friend to take photos! And don’t be the guy that tells her to get her nails done if you’ve never told her that before.

Katie

This is great. Lots of relationships have traditions. For Katie and her husband, it was this restaurant where all their milestones happened. So it was a natural fit for them to get engaged there too. Think about places you two love to go and spend time together.

And I love the tip about a photographer… if you’re wanting to set that up, hey! I know a gal 😉 I’d love to help you with all the planning so she doesn’t even notice I’m there until the question gets popped.

The proposal should be unique to you and your fiancé’s relationship. Over-the-top is nice if your relationship thrives on thrills. If you and your girl are laid back and maybe enjoy romantic walks in the park, think about how to emulate that and make it special. My husband proposed in a park that we go to often, and he had a friend set up a picnic with champagne, dessert, and roses while we were at dinner. It was so intimate and meaningful for us. Now, we can go back to that very same place at that park and think about our proposal!

Jen

Phoning a friend! What a sneaky but smooth move. If you need a few extra hands while you keep the girl distracted to keep her from catching on, friends can be a huge help! Who do you know that can help you pull this off and keep the surprise factor in tact?

Plus remembering to make it sentimental for the two of you is as easy as knowing what you both enjoy. Like Jen said, if you’re a couple who loves big thrills and extravagant acts of love, then those over-the-top proposals make sense. But if you’re not, don’t pressure yourself to come up with something that doesn’t fit your personalities.

The proposal should be intimate. Especially during the age of social media, many people have a need to have a grandiose proposal that is fitting to share with others online. For me, I wanted a proposal that was just Solomon and I, and was centered on our love for each other and not other people. I planned a birthday trip for Solomon to California and we hiked a really tough train / mountain called Mugu Peak. At the top, he proposed to me overlooking the water. There were no crowds, no cameras – it was just us. That intimacy is something that I will cherish forever. We were able to hold a special moment that only us two will remember.

Tkeyah

Guys, this is when knowing your girl will really come in handy. Some girls truly do prefer that special moments like that belong to just the two of you. So there’s no need to stress about making sure her family can fly in or her friends can join you for the big event. Just enjoy the quiet celebration of just both of you sharing that moment in a special way. For Tkeyah, that was perfect. Your girl might be the same. If you’re unsure, think about how she celebrates life’s moments. Does she call her best friend or mom and get excited to show off her news to them? Or does she call you and just update them later? Is she happiest and most herself when there’s a big group of people around her? Or do you see that come out more when you two are alone? The answers to these questions might help you find the right fit.

Don’t act weird or different. Your girl will know what’s up!

Elena

I close with this one because though it’s kinda funny, short, and to the point, it is SO TRUE! I don’t think I need to tell you this but ladies have a sort of sixth sense. We can sense when you are even a little off. It’s due to our overactive brains and electric imagination. So be yourself if you want to surprise her! Don’t act nervous or fidgety. Don’t make plans that seem out of left field. Don’t suggest things to her that you’ve never suggested before (like telling her she should go get her nails done with a friend or suggesting you both take a weekend trip somewhere when you’ve never really traveled much before. She WILL figure out what’s up).

Try to calm down and remember that if you’re both truly at a point in your relationship where you’re ready to propose, the likelihood she’s going to say no is slim. She’s going to be so surprised, but only if you keep it cool.


And now a tip from me! One of my favorite proposal stories I’ve heard was that the bride was actually the one who was “planning” the whole thing, without even knowing it. She was planning a vacation trip for the two of them to go see friends, and he let her pick a restaurant for a special dinner while they were enjoying vacation as well as a few excursions for one of the days their friends would be busy. She was picking all stuff that she wanted to do to create the perfect day. And in the back of his mind, he knew that the cherry on top at the end of that day would be the proposal. She never saw it coming, because he wasn’t even making the suggestions. Just helping her plan a nice day together as a couple.

There are so many ways to keep her off your trail. Another story I love is that the girl really wanted to do a couple’s session with a local photographer. So the groom secretly conversed with the photographer to book it as a proposal session instead. They started the session just like they were getting cute boyfriend/girlfriend photos until suddenly after a few poses, he gets down on one knee and the photographer catches ALL OF IT!! Then the session automatically becomes their engagement session, raw emotion and all.


No matter what you do for your proposal, there is one common theme I saw from hearing these girls’ answers. Make it fit your relationship, and don’t worry about the big, fancy, out of this world proposal. Sometimes intimate moments on a mountaintop hike or visiting a restaurant you frequent often are enough to make it a proposal story she’ll love telling over and over until the end of time!

So deep breaths, guys. You got this!

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When Taylor reached out about having me photograph her Hilton Head Island wedding, I could hardly believe it. Since marrying my husband, I’ve enjoyed annual trips to Hilton Head with my in-laws, who have been visiting for years. I’m not much of a beach person (love my lake life!) but the beauty of the low country made this a top bucket list place for photographing a future wedding. Kolby & Taylor made that a dream come true, as they lived their own dream day! On September 14 at the Omni Hilton Head Oceanfront Resort, Kolby & Taylor tied the knot – and I got to be a Hilton Head Island wedding photographer.

A Hilton Head Island Engagement

Kolby and Taylor met while they were in their respective professional programs. Kolby was attending Duke University for Physical Therapy. Taylor was attending law school at UNC Chapel Hill. They connected pre-Covid, stayed in contact all throughout, and finally met in person when they each returned to campus in August of 2020.

As a couple, they made a habit of exercising together every morning, taking walks and runs to talk about life and their goals. They also love visiting Hilton Head Island, where Taylor’s family lives. The beach is their happy place, where they both enjoy the sunshine and relaxation time. Kolby will listen to a podcast, and Taylor will read her books. They also like to play Spikeball, chat about life, and enjoy the water.

Fast forward a couple years. Kolby and Taylor would travel to spend a lot of time in Hilton Head, where Taylor’s family lives. After what Taylor thought was just a normal weekend visit, they went out to dinner, and her whole family decided to take a walk through a nice park on the water. While posing for pictures, Kolby got down on one knee! That park has now become a special place on the island for the two of them.

Their Hilton Head Island Wedding Day

Their wedding day was a source of some slight anxiety that week. Kevin and I decided to take a week to visit Hilton Head. We celebrated our second anniversary on the island. But the entire week, the weather was not kind to us. It was rainy, chilly, humid, and very few hours of actual sun the entire week. The forecast threatened much of the same miserable wedding for Kolby and Taylor’s big day.

To be clear: RAIN ON A WEDDING DAY IS OK. It’s unavoidable, and you can still get GORGEOUS images on a rainy day. I have plenty of proof of that from Zach & Camille’s wedding, Mary & Joey’s wedding, Kevin & Emma’s wedding, and so many more! My own wedding day still stands as the rainiest wedding I have ever attended, and I LOVE my wedding photos.

But I knew rain would add certain challenges based on their chosen Hilton Head Island wedding venues. Their ceremony was set for the beach at the Omni Hilton Head Oceanfront Resort. I selfishly wished, for the sake of my photos (and for Kolby & Taylor’s experience), that the sun would peek out even if just for the ceremony.

The Lord heard our prayers, because the entire day was fantastic weather!! Our only challenge was the intense wind on the beach, but even that couldn’t affect how beautiful the ceremony was. I shot quickly and took many photos of each shot to ensure we had at least one good option despite windswept hair and dresses.

Between the glorious, glowy sunlight and the wind, their portraits on the beach turned out to be so epic! Taylor’s dress flew dramatically in many of the shots. And her hair and makeup artist deserves a round of applause. Her updo survived and looked gorgeous even as the wind took the wispy pieces left out.

Highlights of the Day

There was so much to love about this wedding. On a personal note, it was my first wedding back in the saddle after giving birth to my daughter! (Birth story soon to come!) Despite worries of feeling a little rusty with postpartum brain fog, I’m feeling bold enough to say this was my favorite/best work yet! Here are some highlights you’ll want to seek out as you scroll:

A Dreamy Tower

Shoutout to Taylor’s friend and bridesmaid Jordan for showing me the tower room at Gull Island Manor, a short-term rental house in Sea Pines! I never would’ve known to wander up there, but it ended up being the dreamiest spot for details and Taylor’s getting ready photos! That light – *chef’s kiss*!

Lean Supplies And A Broken Ring Dish

For the couple’s wedding day details, I really didn’t bring a ton with me from my usually packed styling kit. We had to travel light to fit the essentials. What’s more, my favorite ring dish snapped in half when I dropped it going up the stone steps to the manor!

It was time to get creative. I actually ended up loving the look of my broken ring dish and decided to use it! I also found some dead palm foliage on the outer landscaping to feature in the flat lay of details. Paired with a wisp of Spanish moss, what once was a lean styling kit soon became true-to-location details that made the photos sing “Hilton Head Island wedding.” This just goes to show: Less is more. The less I have to work with in preparation for styling details has sometimes led to my most creative work!

A Touching Island Wedding Ceremony at the Omni Hilton Head Oceanfront Resort

Despite the crazy wind, we were all so grateful for beautiful sunlight during Kolby & Taylor’s wedding ceremony at the Omni Hilton Head Oceanfront Resort. Kolby & Taylor opted out of having a First Look, so I was dead set on getting Kolby’s reaction to seeing his beautiful bride. What I captured was one of the sweetest Groom reactions – instant happy tears as she came down from the dunes.

Another standout moment from their ceremony happened toward the end. Kolby’s dad officiated the ceremony. After a beautiful exchanging of the rings, and just before inviting the first kiss, he began choking up as he pronounced them husband and wife. It was so profound coming from a father (and now father-in-law). You could hear the soft “aww” reactions from the guests. That was such an emotional, happy moment!

Experience > Tradition

Kolby & Taylor planned a truly personal and intimate wedding reception at Gull Island Manor. It more so mimicked a dinner party than wedding reception. They hosted a warm cocktail hour with an open bar featuring their signature cocktails. Guests could explore the grounds while enjoying appetizers and getting their photo taken by the live painter commissioned to watercolor their portrait for a unique take-home gift.

When dinner was ready to start, guests descended to the lower tier of the garden overlooking the marsh. There, a long singular table was set with cheesecloth, candle sticks, place settings, and customized name plates made out of oyster shells.

The couple came down last, but there was no planned fanfare. They decided to forego the traditional dances and simply welcome guests to a laid back dinner serenaded by live musicians. This allowed the couple plenty of time to mingle with each guest and create special memories with the entire party, including a surprise visit from Keebler their dog. I absolutely loved this approach to a wedding celebration – and I could tell everyone else did too!

Final Thoughts From Kolby & Taylor’s Hilton Head Island Wedding

I’m so honored to have served as Kolby & Taylor’s wedding photographer. The entire experience was a dream for me – one that I hope opens the opportunity for even more chances to expand as an HHI wedding photographer. Their warmth and friendship was extended to me from the start, and their guests and family were a true delight to spend the day with.

I’ve begun asking couples to share what they love most about one another, and what excites them for marriage. Here’s how they answered.

What Taylor Loves Most About Kolby

“I love how devoted Kolby is to our little family. He is the most selfless person I know and would do anything to make things easier on others. He supports me emotionally and has the utmost patience when it comes to helping me navigate stressful situations, and he would do literally anything for our dog Keebler. Keebler gets to go to the dog park, walks, gets bones, pup cups, everything! He’s so spoiled because Kolby likes to take such good care of him.”

What Kolby Loves Most About Taylor

“I love how much Taylor guides and anchors me in our life. I am a very good-with-the-flow person which helps me stay optimistic and positive. However, I struggle sometimes with direction and focus because of this. Taylor has given me so much purpose in life and given me the direction for how I want my life to go. She is so ambitious and helps me make goals for ourselves that I would’ve never thought possible. Even in the few years I’ve known her, she’s helped me achieve goals and see a future I would’ve never thought possible for myself and for us.”

The Most Beautiful Thing About Marriage: According to Kolby & Taylor

“The most beautiful thing about marriage in my eyes is the commitment to stand by your partner no matter what life brings. My parents have had a long marriage and I admire the way that they’ve stuck by each other through every challenge. It’s easy to walk away from something when things become difficult but marriage is the commitment to another person to instead engage with them and work through the issues instead of walking away. In my eyes, marriage is beautiful because its permanent.”


K&T, I wish you both so much happiness in your marriage. Enjoy your honeymoon in Europe!!

If you love my work and you’re considering getting married in Hilton Head Island, or another destination in the southern East Coast, I would love to chat! I am based in the DC area but travel often for weddings. Contact me for more information!

Vendor Shoutouts

I was honored to work alongside a vendor dream team, consisting of the following talent:

Kolby & Taylor's Intimate Wedding at Gull Island Manor on Hilton Head Island | A wide shot of Gull Island Manor, available for short-term rental via VRBO

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