Romantic and heartwarming real proposal stories for Proposal Day


What is it about proposal stories? No matter how many we hear, we just can’t seem to get enough of them. Maybe it’s the once-in-a-blue-moon proposals, the kind that make us not just cry, but literally sob with happiness, every time. We probably have these stories to thank for our engagement fascination.

And let us preface, if there are any soon-to-propose guys out there reading this, we apologize in advance. Because these real proposal stories likely might top anything else you had in mind! We’re a sucker for a good love story, and these, in fact, are great love stories.

What did they all have in common? Incredible attention to detail, months of planning, and the best part–they really, really, know the way to their ladies’ hearts. (Girls, feel free to forward this one to your boyfriends–wink wink!)

Ali & Patrick

Wedding date: April 15th, 2015



After dating 5 1/2 years, Patrick surprised Ali in her hometown of Scottsdale, Arizona with the most amazing night of their lives. Being a photography junkie and style blogger (check out her blog here!) Ali loves pictures. So naturally, when the holidays rolled around, she wanted to take a photo to send out to their family and friends. Patrick realized this was the perfect way to plan his proposal. Little did Ali know he had been planning the entire trip back in October! Patrick planted little ideas in Ali’s head to make her think the entire trip and day was her idea.

They made it to Arizona on December 23rd and headed up to the Boulders resort to snap some unsuspecting holiday photos before going to dinner to celebrate Patrick’s birthday.  About 15 minutes into taking the pictures, Patrick turned around and got down on one knee and asked Ali to marry him. Neither one remember exactly what was said, but Ali has no doubt it was “an eloquent and romantic line like something straight out of one of those romantic comedies” she loves so much. (And yes, if you were wondering, those are the exact photos above that were snapped right as Patrick popped the question!)

Still very much in shock, Ali of course gave an emotional “YES!” They then hopped in the car to head to Patrick’s birthday dinner. Upon arrival, Ali quickly discovered it wasn’t Patrick’s birthday party at all, but an engagement celebration, packed with Patrick’s and Ali’s families! After dinner, they headed to the Four Seasons for a glass of champagne, only to find another surprise–all of Ali’s best friends from high school, there with balloons and bubbly, to wrap up the best night of their lives.

Cue our hearts melting.

Kayla & Adam

Wedding date: TBD!


While most mid-20-somethings spend the majority of their non-working hours at a yoga studio, coffee shop, or local bar trying to find their perfect match–Kayla found hers in the only natural place for a traveling management consultant–the airport! She and Adam locked eyes at Chicago’s O’Hare airport after a 6 hour delay out of London, causing her to miss her connecting flight. The two went full speed ahead, and arranged a date at Chicago’s Field Museum.

Both being history lovers, it was the perfect setting to get to know one another, wandering the halls of the gorgeous museum together. The two ended the day with some silly photo booth pictures that found a forever home in a pencil jar in Adam’s home office in Michigan.

Fast forward years later–Kayla had a feeling a proposal was in the near future. (After all, he is a doctor, things are always perfectly calculated!) They had a standing tradition of taking silly photos each year with a different photographer, each with a unique and interesting style. When he INSISTED on picking the photographer and coordinating the shoot–she knew something was up, and had a feeling he’d use this opportunity to propose. Adam, being the smartypants he is, threw her a curve ball, and didn’t plan to propose at the shoot at all, but asked her to go back to the Field Museum on a sunny Saturday in July, re-creating their first date.

Upon arriving, Adam lead Kayla’s hand up the stairs (uncharacteristic public displays of affection, already pre-purchasing their tickets, she was getting suspicious.) The couple walked through the Asian history exhibit and then into the Gem hall, where they browsed and chatted, among the other visitors admiring the beautiful stones.  On the way out, Kayla noticed a case on the left hand side of the doorway. She peered closer, and noticed that inside the case was the same reel of photos they had taken at the photo booth on their very first date to the Field Meseum, as well as a note, and a diamond ring! When she turned back around, he was down on one knee!

It’s no wonder Kayla didn’t notice the people around taking photos, watching, and cheering. All she was focused on was Adam, and how he pulled off the most detailed and shocking proposal she could have ever dreamed of.

(We’re seriously impressed, Adam!)

Blake & Ian

Wedding date: June 11th, 2016



When Blake was planning her girls trip getaway to Paris, she never expected such big surprise in the city of romance. Upon arriving to Paris Monday evening, Blake and her girlfriends quickly threw their bags down in their hotel and booked it to–what else? The Eiffel Tower, just in time to see those oh-so-famous twinkling lights. But the girls hadn’t had their fix yet, and vowed to return the next day to see the view of the city in the daylight, from the tip top of the tower.

The next day was a dream as far as girls trips go, and started with a picnic at Notre Dame’s park, then to the Pont de l’Archeveche, also known as “Love Lock Bridge.” Knowing his girlfriend was heading to the city of love, Ian had surprised her by giving her a lock with their names on it, so the couple could forever leave their mark on the city of romance, even if Ian couldn’t be there in person.  Fast forward a few weeks, and Blake found herself the perfect spot to put her lock, and tossed the key into the river, thinking of Ian all the while, hundreds of miles away back home in the U.S. (Or so she thought.)

The girls then headed back to the Eiffel tower, this time to take the elevator all the way up to the top floor. The moment she’d been dreaming of for weeks was finally here! What could be better than being at the top of the Eiffel tower with a champagne buzz and your best girlfriends? She was about to find out!

Blake was admiring the beautiful view of Paris when she turned around to find–who else? Ian! (Along with all of her best friends) standing right beside her. He had flown all the way from California to Paris to surprise her. Because, who wouldn’t take advantage of proposing on the Eiffel Tower? We’re so glad he jumped at the once in a lifetime opportunity, because it made for a once in a lifetime proposal story!

Michelle & Jon

Wedding date: August 29th, 2015



Michelle prefers to refer to the day Jon popped the question not as, “the proposal,” but “a highly choreographed, stealth operation.” Although her friends and family knew about the day and their roles and responsibilities several months in advance, nobody muttered a word. “I don’t know if I should be impressed or concerned,” Michelle laughs.

It was Saturday, July 26th and Michelle and Jon were going out for brunch and mimosas in Chicago, much like any other typical Saturday. But when Jon got up to sneak off to the bathroom a third time, Michelle knew something was up. Only this time, he didn’t come back. She felt a tap on her shoulder and upon turning around, she discovered not Jon, but her two sisters, who had flown in from Atlanta standing there! After many tears and hugs, they handed her a gift and a note from Jon, which was a recipe box (Michelle is a foodie and excellent cook) a love note, and one recipe card with a clue and instructions on where to go next. A love scavenger hunt representing their entire relationship was about to begin.

Cue the next scene–Michelle’s two friends from work pulled up in a car to take her to destination #1–the first place the couple met. When she arrived at the apartment (they met at a house party), more friends were there to greet her and hand over the next recipe card clue: the location of their first date. She walked through the doors of Chicago’s Sunda to find her two best friends (one who had flown in from Nashville!) “I was ugly crying at this point!” Michelle said.

The next stop was the Chicago Theatre, where the couple shared some of their favorite memories. When Michelle arrived, she was met by her future in-laws, who had flown in from Raleigh! Jon’s sister, brother-in law, and uncle were all there to deliver the next recipe card, which took her to Wrigley Field. It was a crowded day in Wrigleyville for the Cubs game, but when Michelle spotted her mom from a distance, she lost it. Both Michelle and Jon’s parents were there to exchange more tears, sweet notes from Jon, and her last and final clue: Diversey Harbor in Lincoln Park–a place along lake Michigan they love to sit and admire the Chicago skyline.

The whole group from the day met Michelle at the harbor. When Jon came out from around the corner with the final note, Michelle knew what was coming. He got down on one knee, and gave Michelle the most beautiful ring she’d ever seen.

But the celebration wasn’t over yet! Jon had planned an engagement party with plenty of deep dish pizza and wine (Michelle’s favorites). They then made their way to a street festival with the full entourage in-tow. After that, Jon had rented out a bar/bowling alley, and they partied until last call!

And as if you weren’t already in tears, Jon asked Michelle’s sister (who just happens to be a wonderful videographer) to film every step of the way. Get your tissues out for this one, ladies!

Do you have a great proposal story? Please share it with us below! (Really, we can’t get enough!)


jesskeyesbioJess Keys is a graduate of Indiana University, a Chicago transplant and Founder of The Golden Girl Blog. She was first bitten by the wedding bug at age 11, when she purchased her first Brides magazine in the Lexington, KY airport. She’s partial to red lipstick, French Bulldogs, and a lover of the written word. You can often find her at the closest Dim Sum establishment, or exploring the Windy City with her camera in tow.