How to Propose: The Ultimate Guide to Planning a Proposal in Madison Wisconsin
Thinking about popping the question in Madison? You’re in the right place. This ultimate guide walks you through the seven key elements of planning a proposal—from finding the most romantic spots to mapping out the perfect post-proposal celebration, and everything in between. As a professional proposal photographer, I’m here to make the process easy, meaningful, and completely you. Let’s dive into how to pull off the perfect proposal, start to finish.
1.Consider the Elements of the Proposal
Public or private? Think about what kind of setting your partner would love most. Would they feel more comfortable with a quiet, private moment—something intimate where you can really connect? Or would they love the energy of a public space, maybe even a crowd cheering after the big “yes”? There’s no right or wrong here—it’s all about what feels most them.
Family and friends? Another thing to think about: Would they want loved ones involved? This could mean having family and friends nearby during the proposal, or just celebrating with them afterward. I’ve even photographed surprise proposals disguised as a family photo session! Some couples go big with family plans, others keep it just the two of them and share the photos later. As a proposal photographer I can say with confidence that both options are good opinions so just think about what your partner would want—not what others might think.
2. Choose a Location — Best Outdoor Locations to Propose in Madison
Picnic Point
Picnic Point offers a beautiful yet easy walk on a small peninsula extending into Lake Mendota. This popular trail is well-loved for good reason. It features prairie and wooded areas, with several scenic lake views along the way. Taking a stroll out to the point on a summer or fall evening is a peaceful and romantic way to set the stage for your proposal.
Tenney Park
Tenney Park offers a variety of scenery with two main areas—the waterfront on Lake Mendota and the lagoon. The lakefront includes a beach and a breakwater located at the locks of the Yahara River. The lagoon features several picturesque bridges and winding paths through a large grassy area surrounded by water. The breakwater is lined with benches, making it a romantic spot to watch the sunset—and a perfect place to propose!
State Capitol & Capitol Square
The State Capitol is Madison’s most iconic building and my top pick for an “urban” proposal location. The Capitol sits on beautiful grounds with mature trees and gardens. The architecture is stunning and makes for a dramatic, elegant backdrop if you’re looking for a more city-style proposal. Capitol Square is also home to many great restaurants—perfect for a celebratory dinner afterward.
Olbrich Gardens
This 16-acre botanical garden is a gorgeous location with a great mix of flowers, trees, brick paths, and unique structures. There’s a peaceful bridge and even a small Japanese garden. Walking through Olbrich is always a treat, and it offers plenty of beautiful spots to pop the question.
UW–Madison Arboretum
A favorite among both locals and visitors, the Arboretum has something for every season—flowering trees and gardens in the spring and early summer, and stunning prairie walks in the fall. There are wooded trails and scenic paths throughout. Whether you're envisioning a quiet moment in the gardens or a cozy walk through the woods, the Arboretum has a little bit of everything.
Pheasant Branch Conservancy
This beautiful 682-acre protected area is technically in Middleton, just west of Madison. It features prairies, meadows, an open-water marsh, forested trails, and a creek that winds through the landscape. With several scenic bridges and quiet paths, it’s a peaceful and natural setting for a thoughtful, low-key proposal.
Memorial Union
Located on the south shore of Lake Mendota on the UW–Madison campus, Memorial Union is known for its iconic terrace—a lively spot with lake views, local beer, music, and great sunsets. There are also several nearby docks, which make for a quiet, intimate proposal spot just steps away from the energy of the terrace.
Monona Terrace
Right on the shore of Lake Monona in downtown Madison, Monona Terrace is just a few blocks from the Capitol. The rooftop terrace features fountains and sweeping lake views, making it a great place for a lakeside stroll or a sunset proposal. Bonus: the building was designed by Frank Lloyd Wright, adding a little architectural charm to the moment.
A State or County Park Near Madison
There are so many amazing parks near Madison that make beautiful, natural proposal locations. Some top picks:
Devil’s Lake State Park
Governor Dodge State Park
Lake Kegonsa State Park
Token Creek County Park
Blue Mound State Park
Capitol Springs
Parfrey’s Glen
Ferry Bluff
Governor Nelson State Park
Each of these has unique features—from dramatic bluffs to quiet forests—and could be the perfect backdrop for your big question.
Choose How to Capture the Moment— Hire a Photographer or take another route
Hire a Professional Photographer
This is a once-in-a-lifetime memory, and having it photographed means you’ll get to relive every look, every laugh, and every happy tear for years to come. As a proposal photographer, I can tell you—without exception—that the reaction is always the same: total joy that the moment was captured forever.
How Does Hiring a Photographer Work?
When you bring me in as your photographer, I’m not just standing off in the distance with a camera. I’ll help you plan out the details so everything feels natural and stress-free for you—and unforgettable for her.
There are two main approaches:
The Hidden Photographer – I’ll be waiting discreetly at the proposal spot, camera ready. When you drop to one knee, I capture every second without her noticing until the big reveal.
The “Couples Session” Trick – If you want something a little less suspicious, you can surprise her during what she thinks is just a professional photo shoot. We’ll start with a few casual poses, and then at just the right moment, you’ll propose while I capture it all.
Both options keep the focus on your story while making sure you walk away with beautiful, timeless images. [Link: Learn more about my process here]
Other Ways to Capture the Moment
Of course, you don’t have to hire a photographer. You could set up a tripod, ask a friend to take photos, or even keep it completely private and capture it in words afterward. But here’s the thing: you only get one chance at this moment. If having it beautifully documented matters to you—or you know it will matter to her—bringing in a professional is one of the best gifts you can give.
4. Decide on a Ring
About 90% of people propose with a ring—and in all of the 50+ proposals I’ve photographed, every single one involved a ring. One of the biggest hesitations I hear is: What if she wants to pick out the ring herself? Or maybe you’re just not sure what style she’d love. If that’s holding you back, there’s a simple solution: propose with a “placeholder” or “dummy” ring, and then choose the real engagement ring together afterward. That way, you still get the magic of proposing with a ring without the stress of getting it wrong.
Things to Keep in Mind When Choosing an Engagement Ring
Diamonds aren’t the only option. While diamonds are the most popular, she may prefer a gemstone like a ruby, sapphire, or emerald.
Lab-grown vs. natural diamonds. Lab-grown diamonds are nearly identical to natural ones in appearance and quality, but they’re often up to 60% less expensive—and they’re becoming more and more popular.
Non-Diamond Alternatives
If you know she’s not set on a diamond, there are some incredible alternatives that can feel more personal and unique:
Sapphires – Known for their deep blues but available in a range of colors, sapphires are durable and timeless.
Emeralds – A bold, vibrant green stone that makes a statement and pairs beautifully with gold.
Rubies – Symbolizing love and passion, rubies add a striking pop of color
Moissanite – A sparkling, affordable alternative to diamonds that looks almost identical but comes with a lower price tag.
Choosing a non-diamond ring can be a thoughtful way to match her personality and style—plus, it often makes the ring stand out as something truly one-of-a-kind.
The Best Engagement Ring Jewelers in Madison
Jewelers Workshop (est. 1969) – Known for combining classic craftsmanship with modern technology, they create every piece in-house, ensuring lasting quality.
Soha Diamond Co. – A husband-and-wife jeweler team with ten generations of experience. They specialize in ethical, sustainable jewelry, perfect if you want values to be part of your story.
Chalmers Jewelers – Offers a wide selection of engagement rings and custom designs, with a strong reputation for working closely with couples to create something unique.
Kesslers Diamonds – Specializes in custom diamond rings and is well-known for their “no small print” lifetime warranty.
Goodman’s Jewelers – With over 90 years in business, they pride themselves on honesty, integrity, and a welcoming boutique experience.
5) Make a Celebration Plan – Decide How You’ll Celebrate After Popping the Question
Once the ring is on her finger and the happy tears are flowing, trust me—you’re both going to be on cloud nine. That post-proposal high is unforgettable, and the best way to keep it going is by having a celebration plan ready. Instead of asking “what should we do now?” in the moment, you’ll already have something special lined up to carry that joy forward.
A Romantic Dinner Date
A classic choice that never fails. Book a table in advance so you’re guaranteed a spot. You could go all out at one of Madison’s upscale restaurants like L’Etoile, Sardine, Rare Steakhouse, Heritage Tavern, Pig in a Fur Coat, or Fairchild. Or, if you’d rather keep it cozy, choose a favorite spot that already means something to you both. Want a little extra flair? Try one of Madison’s rooftop restaurants like Eno Vino Downtown for dinner with a view of the city lights.
Celebrate with Friends
If she’s close with her friends, imagine walking into a bar or restaurant afterward and seeing them all there, ready to toast your engagement. It’s a fun way to turn your proposal into a shared memory with the people who know you best.
Celebrate with Family
For some couples, family is at the heart of everything. Planning a gathering with parents, siblings, or even just a few close relatives can make the moment even more meaningful. Whether it’s brunch the next morning or a surprise dinner the same night, celebrating with family can set the tone for all the memories to come.
Plan a Fun Activity Together
If going out isn’t your style, there are plenty of creative ways to keep the celebration going:
Have e-bikes waiting near your proposal spot and take a joyful ride together.
Rent a boat on Lake Wingra for a romantic, private escape
Surprise her with tickets to a show or concert you know she’ll love.
Spread out a picnic in one of Madison’s scenic spots.
Keep it intimate with a date night at home—think flowers, candles, her favorite takeout, and a bottle of champagne.
Or simply grab a meal and drinks at the place you both love most—it’s all about being together and soaking it in.
Whatever you choose, remember: the celebration doesn’t have to be extravagant. It just needs to feel like you. With a little planning, the joy of saying “yes” can flow right into an evening (or weekend!) you’ll both remember forever.
6) How to Get Your Soon-to-Be Fiancée to the Location (Without Giving Away the Surprise)
One of the trickiest parts of planning a surprise proposal isn’t choosing the ring or the words—it’s figuring out how to get her to the spot without raising suspicion. As a photographer who’s helped plan and photograph over 50 proposals, I can tell you: having a solid plan makes all the difference.
Here are a few questions to help you think it through:
What does she naturally enjoy doing? Think of activities that feel “normal” so she won’t suspect a thing.
A walk at the Arboretum, Picnic Point, or another park like Olin or Hoyt.
Watching the sunset at Tenney Park, James Madison, or Memorial Union.
Visiting a beautiful spot like Pheasant Branch Conservancy, Olbrich Gardens, or Allen Centennial Gardens.
Does she love certain atmospheres?
Prairies, lakes, or curated gardens all set a beautiful scene—and if it’s something she already enjoys, it won’t feel out of place.Is there a place that already means something to you both?
A favorite coffee shop, bar, or restaurant can be just as meaningful as a scenic overlook.
Would she be excited about a “reason” to dress up?
Suggesting a couples photo session is a great way to get her to a location without suspicion. A few poses in, you drop to one knee—and she’ll never see it coming.
If you decide to hire a photographer, this is one of my favorite ways to help. I’ll guide you toward the best locations, the perfect lighting, and a plan that feels natural to her but stress-free for you. By the time you propose, you’ll feel confident knowing everything is in place—and she’ll be swept away by the moment.
7. Plan What You’re Going to Say
There’s no single “right” way to propose—but taking a little time to think about your words will help you feel calm and confident in the moment. Proposing is emotional, and nerves are totally normal. Having a plan ensures that, even if your heart is racing, you’ll still say what matters most.
Speak from the Heart
The most powerful proposals are the ones that feel genuine. Think about why you want to spend your life with her, what makes your relationship special, or the moment you knew she was “the one.” You don’t need to memorize a speech—it’s more about sharing what’s in your heart.
Write Down a Few Notes
Jotting down a few ideas ahead of time can keep you from blanking out when the nerves hit. You might write down:
A favorite memory you share.
The qualities you love most about her.
A vision of your future together.
The simple but important words: “Will you marry me?”
Keep It Simple
Don’t feel pressure to deliver a perfect monologue. She’s not expecting Shakespeare—she just wants you. A few heartfelt sentences will mean more than a long, rehearsed script.
Practice (But Not Too Much)
Reading your notes out loud once or twice can help you feel comfortable with your words. After that, trust yourself. In the moment, let your emotions guide you.
At the end of the day, she’ll remember the joy, the love, and the way you looked at her—not the exact wording. If you speak from the heart, you can’t go wrong.
Bonus: When the Moment Arrives, Don’t Rush It
After all the planning, the nerves, and the details—you’re finally here. This is the moment you’ve been imagining, and it’s going to be one of the most memorable in both of your lives. When it happens, don’t feel like you have to rush. Take a breath. Look at her. Let yourself soak in every second.
Whether you deliver the words exactly how you practiced or your emotions take over, what she’ll remember most is the love behind them. Give yourselves space to laugh, cry, hug, or just stand together in the happiness of it all.
Your proposal is more than just asking a question—it’s the start of a new chapter. By slowing down and being fully present, you’ll create a memory you’ll both carry forever.
And if you want that memory captured in a way that you can relive for years to come, I’d love to help. As a proposal photographer, I not only document the moment, I also help with the planning so everything feels natural and stress-free. If you’re ready to start planning your proposal in Madison, [reach out here]—I’d be honored to be part of your story.
Planning a proposal in Madison, Wisconsin? With a little thought and the right photographer, you can turn your question into a timeless moment you’ll both treasure forever.”