Seeking: How a sugar baby dating site underwent a drastic transformation with new Gen Z boss

The world's largest luxury dating site with over 52 million users and a stigmatic past has undergone a drastic transformation with a new Gen Z co-CEO.

Some people may be familiar with Seeking, formerly known as Seeking Arrangements, a dating site once synonymous with the sugar dating scene. But, where did it all start?

Brandon Wade, 54, founded the site in 2006 after trying out various dating agencies and mainstream sites with no luck. This was the driving force behind his new venture, coding around the clock to create the avant-garde approach to online dating.

"Our goal remains steadfast in helping success-minded people find what truly makes them happy, whether it is romance, travel, luxury, freedom, or whatever it is they aspire to in their connections," he once explained.

Brandon found love on his very own site with his "soulmate" and wife Dana Rosewall, 24, who has since joined forces with her husband in her role as co-CEO.

Dana, who was working as an economic researcher in Florida while actively using the dating site, aims to expand Seeking's philanthropic initiatives in eliminating fraud, protecting women's safety and encouraging meaningful hypergamous relationships.

Courtesy of Dana Rosewall

Dana didn't shy away from the earlier stigmas of Seeking. Terms including 'gold diggers' among other harsh names were thrown around online – and unsurprisingly, the men on the site were rarely criticised.

Dana believes this judgement is simply unwarranted and outdated.

"The idea that if a woman wants to date a successful man who she admires and looks up to equates to ‘sugar dating’ is a narrative that did not appeal to me, and it no longer fits our community either," Dana tells Indy100. "Our dream is for our brand to reflect this reality: that Seeking is the go-to dating platform for inspiring love stories that people aspire to. I call it modern hypergamy."

Traditional hypergamy was once rooted in marrying for financial gain. Now, a modernised trend has been sweeping the US and UK with a recent survey revealing a staggering 57 per cent of people seeking out love interests who "complement" their own attributes with singletons looking for partners with intellectual, cultural, lifestyle and economic aspirations.

"Modern hypergamy is about much more," Emma Hathorn, dating and relationships expert, says. "It reflects a shift towards valuing growth and shared benefits in relationships. Today, ambition, wealth, and status remain important, but it's equally essential to find a partner who complements and enhances your life in meaningful ways."

Dana agrees. While acknowledging that the dating trend is often perceived as "old-fashioned," one of her main goals is to ensure Seeking has a better representation of the young women who use it.

"Hypergamy is the desire to date up, but 'modern hypergamy' is about the desire to uplift one another, to give and receive equally, as represented by my relationship with my husband," she explains.

Courtesy of Dana Rosewall

Modern hypergamy, or hypergamy 2.0, is the direction Dana plans on taking Seeking.

"As the concept is evolving, we believe that a relationship can be something that enhances your life, as long as the heart of it, it’s from a place of genuine love, respect, and mutual support. This shift is key to fostering authentic connections in today’s dating landscape," she shares.

Aside from shifting Seeking away from older stereotypes, Dana wants the dating site to be a safe haven for people looking to build relationships that "balance and uplift" one another, by moving away from the sugar dating model and more towards "building authentic connections".

Her priority is to completely eliminate fraud from the dating platform, and while fraud across social media and other mainstream dating platforms is prevalent, Dana wants to make Seeking "the benchmark for the online dating industry".

"Tackling the issue of fraud and fake profiles is no small task, and can result in a dip in revenue," she says. "However, I believe that it’s necessary to uphold our website's values and show people that online dating can be a safe, genuine space to find meaningful connections."

Dana says unlike many CEOs who are often "profit driven and shareholders," she has the advantage of being financially independent, allowing her "to make tough decisions that put our users' needs first and benefit their user experience."

Courtesy of Dana Rosewall

Women's safety is, rightfully so, a top concern for Dana and one she "takes very seriously".

The co-CEO started her new role by delving into the real-life concerns of the women on the platform and acting on them to make the relevant changes.

"I believe that listening to our audience is the best place to start - women must be heard and taken into consideration, and each voice is important to improving the safety standards on the platform and for us to prioritise safe and authentic connections," Dana says.

She will be implementing a system that only allows verified, authentic users, along with the existing 24/7 global team and AI tools monitoring site activity.

"We believe that there is always room for improvement, particularly where women’s online and offline safety is concerned," she adds.

While Dana's plans are in motion, she acknowledges Seeking is very unlikely to go mainstream due to the oversaturation of dating apps.

Their niche approach "allows for a much more effective approach to dating and relationships with quality versus quantity front of mind".

"Quality means our users will find what they are looking for faster, instead of dating on mainstream platforms where quantity leads to more time wasted on dating apps – which we've found a lot of people moving away from," she adds.

Dana rounds off by saying anyone can register to join Seeking with "no strict requirements at present", but it tends to draw a crowd who are career-minded and ambitious while acknowledging the two as subjective to each individual.

"Our priority is ensuring the safety, security, and integrity of the community, so future updates will focus on enhancing the quality of connections while upholding the values that make Seeking unique," she adds.

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