The Art of Modern Proposals: How “Popping the Question” Has Become an Extravagant Affair

Rafael Usufally knew that when it came time to propose to Alexandria Kishore, his girlfriend of 11 years, he wanted to create a moment as extraordinary as their relationship. For Rafael, an electrical engineer from Long Island, the cost was secondary to the experience he wanted to craft. He spent weeks searching for the perfect ring, eventually settling on an $11,000 radiant and emerald cut diamond creation with a diamond-filled band—more than double the national average for engagement rings. But the ring was just the beginning. Rafael enlisted an event planning company, spending $2,200 on a proposal package that included a private photographer and beautiful decorations for a private room at a Manhattan skyline-facing restaurant. When Alexandria walked into the stunning, candle-lit space filled with hundreds of scattered rose petals to find Rafael on one knee, she was completely surprised. “My heart stopped at that moment; it was so surreal,” she recalled. Their total proposal cost reached $14,050—nearly half the price of an average wedding—but for them, the memory created was priceless.

The days of simple proposals seem to be fading as elaborate engagements become the new norm, inspired by celebrity spectacles like Travis Kelce’s $38,000 custom-decorated garden proposal to Taylor Swift or Jeff Bezos proposing to Lauren Sánchez on his $500 million superyacht in the Mediterranean. Yet this trend isn’t limited to the rich and famous. Event planners report working with everyday clients who request helicopter rides, private pier proposals with family-filled boats arriving afterward, custom floral installations, live musicians, and professional photographers to capture every moment. The rise of social media has undeniably fueled this phenomenon, creating what wedding planner Lauren Zizza calls “proposal culture”—where there’s subtle pressure to make the moment not just emotionally significant but visually stunning enough to share online. For many couples, these extravagant gestures aren’t merely about showing off but about creating a once-in-a-lifetime memory that reflects the profound importance of their commitment.

Phil Kessler embraced this philosophy wholeheartedly when planning his proposal to now-husband Zack Aberman Kessler in May 2022. Originally planning a trip to the Hamptons, Phil realized they could travel to Europe for a similar investment and chose Portugal as their destination. The video game designer, who admits he doesn’t believe in setting budget limits for significant moments, booked a $1,000-per-night five-star hotel and treated Zack to a luxurious lunch with a $200+ bill at a cliff-side restaurant overlooking the ocean. Later, during a stroll along a picturesque beach that Phil describes as “the most beautiful place I’ve ever been in my life,” he got down on one knee and presented not one engagement ring, but two IWC Schaffhausen watches totaling $12,000—same model but with different colored faces and band styles. A hired photographer captured the emotional moment, bringing the total proposal cost to over $17,000. Despite the expense, the couple maintains it was “the best day of our lives, even better than our wedding.”

Similar sentiments are shared by Michael Loconte and Shannon Ganley, who turned what appeared to be a celebration trip for Shannon’s master’s degree into an unforgettable proposal at Lake Como, Italy. Michael, who works in financial software, arranged a $500 private boat tour around the beautiful town of Varenna, where he surprised Shannon with a diamond engagement ring valued between $10,000 and $15,000. To capture the special moment, he hired a photographer for $1,142 under the guise that the photographer was taking promotional pictures of the boat. When the “boat photographer” suggested taking a picture of the couple with the marina in the background, Shannon began to suspect something special was about to happen. “This could be happening. Oh, my God,” she thought to herself moments before Michael proposed. Following the emotional moment and Shannon’s enthusiastic “yes,” the newly engaged New Jersey couple celebrated with drinks followed by a $351 dinner with a full tasting menu before finishing their evening at a wine bar. Their Italian proposal totaled $17,193—a significant investment for a single moment, but one that created memories they’ll cherish forever.

The transformation of proposals from simple, intimate moments to elaborately planned productions reflects broader changes in how we celebrate milestones in the social media age. Twenty years ago, the average wedding cost around $20,000; today, some couples are spending nearly that amount just on the proposal. This shift raises questions about expectations, authenticity, and the true meaning behind these gestures. Are these extravagant proposals driven by genuine desire to create something special, or by external pressure to meet an increasingly high bar set by celebrities and influencers? For the couples featured, the answer seems clear—while the financial investment was substantial, the emotional return on that investment made it worthwhile. They describe their proposals as among the most meaningful moments of their lives, sometimes even surpassing their weddings in emotional significance.

What remains constant across these stories is the underlying emotion that drives these grand gestures—love and the desire to create a meaningful beginning to a lifelong commitment. Whether it’s Rafael transforming a restaurant space into a rose-filled wonderland, Phil choosing watches that symbolize how he and Zack will spend time together for the rest of their lives, or Michael selecting the breathtaking backdrop of Lake Como to ask his most important question, these proposals represent deeply personal expressions of love. While the average cost of these featured proposals ranged from $14,000 to over $17,000, the couples emphasized that the memories created were invaluable. As proposal culture continues to evolve, perhaps the most important consideration isn’t the price tag but whether the moment authentically reflects the unique relationship being celebrated. After all, while photographs may capture the perfect setting or the exact moment a ring is presented, what truly matters is the genuine connection and commitment being formed—something no amount of money can buy.