I remember vividly the nervous excitement I felt just over ten years ago, stepping into the Black Tie & Lingerie Ball, held over a magical New Year’s weekend at the Ritz Carlton. Picture this: gowns and tuxedos, elegant smiles, and an intimate performance by The Wailers (yes, those Wailers – of Bob Marley fame) at a private estate. My heart raced, not out of anxiety, but out of excitement for the possibilities ahead.

At that time, I was single. Even so, the atmosphere immediately put me at ease. It was sophisticated, elegant, respectful, and genuinely welcoming. Although most attendees were professional couples, there was always a small but delightful group of other single women to meet, laugh with, and, yes, even share a wink across the room as we navigated this intriguing new social space together. The few single men who attended were, as the host George affectionately says, “best of breed”, charming, respectful, and carefully vetted. Most were prior members with their partners, so they knew the lay of the land.

Since that unforgettable evening, I attended several more events on my own, each time becoming more comfortable, each time feeling more connected to the vibrant, open-minded women I met along the way. Gradually, George (who is now my husband) and I decided we wanted to cultivate this feeling, this community, into something even more intentional and inclusive. That’s how The Group was born.

Today, I am proud and excited to see how far we’ve come. Single-gender spaces have become a core element within The Group’s offerings. From our elegant Just For Dinner: Ladies-Only events, exclusive evenings designed to encourage genuine conversations and connections, to our spirited and empowering play parties like Stiletto Social, there are abundant opportunities for women to explore comfortably, freely, and at their own pace.

We’ve even hosted indulgent co-ed weekends at luxurious retreats like the Four Seasons, where we booked out the entire spa exclusively for women, allowing a perfect space to relax, unwind, and form genuine friendships in a private and supportive environment. It’s during moments like these, surrounded by laughter, mutual support, and genuine openness, that the true magic of The Group shines brightest.

If you’re a single woman reading this, curious yet perhaps feeling hesitant, I want you to know something crucial: at The Group, privacy and discretion aren’t just buzzwords; they are foundational commitments. But just as important is the unwavering dedication to consent and mutual respect. These values are constantly emphasized and deeply respected by every member of our community.

So, whether you’re interested in exploring an open, elegant lifestyle or simply looking for a supportive community of incredible women who share your curiosity, you’re warmly welcomed here. Consider this your personal invitation to connect, whether by attending an event, requesting an invitation, or simply reaching out to me directly. I’m always up for a chat.

Looking forward to welcoming you with open arms.

Kisses,


Ann


Co-Founder, The Group

The post Sophisticated, Single, and Curious? A Note From Ann first appeared on The Group.

As we embrace a fresh season of connection, warmth, and exploration, Stiletto Social is thrilled to announce our first yacht party of 2025, setting sail from the dazzling shores of Miami Beach on Saturday, May 17th.

Stiletto Social, lovingly curated by The Group’s co-founder Ann, has long provided women a sophisticated, welcoming, and empowering space to connect and celebrate themselves—regardless of relationship status or sexual orientation. This extraordinary yacht experience continues our tradition of creating luxurious and meaningful environments where women can express themselves authentically, safely, and joyfully.

Imagine the sun setting on your skin, champagne in hand, surrounded by vibrant, like-minded women who understand the thrill of exploration and the elegance of discretion. From the carefully selected music to the thoughtfully curated refreshments, each element is designed to encourage connection, laughter, and perhaps even a touch of adventure.

Whether you are single, coupled, or simply curious, Stiletto Social warmly welcomes you (just leave your male partner at home). This is your chance to build genuine friendships, experience meaningful connections, and explore the boundaries of your comfort zone at your own pace—always with consent, respect, and absolute discretion.

If you’re new to The Group or Stiletto Social, you’ll quickly discover the warmth and openness that sets our community apart. Privacy, discretion, and consent are not merely ideals; they’re foundational values deeply embedded in every event we host.

Join us on May 15th in Miami Beach as we sail into a day of elegance, empowerment, and unforgettable connection.

Request Your Invitation at www.Stiletto.Social

Spaces are limited, and requests for invitations are already coming in—secure your spot now, and let’s embark on this beautiful journey together.

The post Yacht Chic: Ladies-Only Party in Miami—Saturday, May 17th first appeared on The Group.

The night’s success can be captured in the words of Ann, the visionary hostess behind Stiletto Social, “It was a magical night of women enjoying each other without judgment, and I am even more excited for the next one.” Indeed, the atmosphere was one of pure camaraderie, with women freely expressing themselves and forming bonds that will last far beyond the event itself.

Stiletto Social comes to Miami

Building on this momentum, Ann is thrilled to announce that the second Stiletto Social will take place in the vibrant city of Miami, Florida. Known for its vibrant nightlife and beautiful scenery, Miami is the perfect backdrop for the next chapter in the Stiletto Social series. This exclusive event promises to elevate the experience even further, offering an evening of unparalleled connection, entertainment, and fun.

Las Vegas DJ

We are also excited to welcome back DJ Ashlee Lynzee from TAO Nightclub in Las Vegas, who will again set the perfect mood with her signature blend of beats. Her performance at the launch party was one of the night’s highlights, seamlessly blending high-energy tracks with the relaxed, intimate vibe of the event. With Ashlee behind the decks, the Miami party is set to be an unforgettable night of music and dancing under the stars.

The essence of Stiletto Social lies in its inclusivity and the unique opportunity it offers women to connect on a deeper level. Whether you’re single, married, or somewhere in between, regardless of your sexual orientation, this is an event where you can be yourself, free from judgment, in a supportive and empowering environment.

By Invitation Only

The event remains selective and by invitation only, ensuring an intimate and enjoyable evening for all attendees. This approach to sapphic intimacy maintains the exclusivity of the experience and ensures that everyone who attends is aligned with its spirit—a night of genuine connection, fun, and empowerment.

If you’re interested in participating in this exclusive experience, we invite you to request an invitation at www.Stiletto.Social. This is more than just a party; it’s a community of like-minded women coming together to celebrate life, love, and friendship in a truly private setting.

Don’t miss out on what promises to be another incredible night. Request your invitation today and prepare to enter a world where connections are made, and unforgettable memories are created.

See you in Miami!

The post Stiletto Social Takes Off: A Night to Remember and a New Destination first appeared on The Group.

Mark your calendars for a unique celebration of femininity and connection as The Group proudly announces the Stiletto Social Launch Party. This ladies-only on-premise event is scheduled for 9 PM on Saturday, August 3rd, aboard a private yacht in Fort Lauderdale. It’s not just a party—it’s a journey into a night filled with elegance, empowerment, and exclusive experiences.

An Invitation-Only Affair

Stiletto Social is an invitation-only event that promises to be as selective as it is spectacular. By borrowing from the successful format of our acclaimed “Jackets Required” gatherings, this soirée is set to start with a lightly catered cocktail reception. Guests will be welcomed aboard with a variety of gourmet bites and a selection of fine wines and artisan cocktails, setting the tone for an evening of sophisticated socializing.

From Cocktails to Connection

As the evening progresses, the atmosphere will organically evolve into a more intimate sapphic experience. What begins as an elegant mixer will gently transition into an opportunity for guests to explore deeper connections and shared interests. The yacht will provide the setting haven for this transformation, offering both privacy and luxury against the backdrop of Fort Lauderdale’s stunning coastal views.

An Evening Hosted by Co-Founder Ann

We are thrilled to announce that the evening will be hosted by none other than The Group’s co-founder, Ann. Known for her grace, elegance, and commitment to creating empowering spaces for women, Ann will ensure that the party is not only memorable but also a true celebration of women’s empowerment and sisterhood.

A Celebration of Sapphic Sisterhood

“It’s an opportunity to meet other women and form bonds that could last a lifetime,” says Ann.

Stiletto Social is more than just a party; it’s a statement. It’s about creating a space where women can feel safe expressing themselves freely, connecting with like-minded individuals, and celebrating their identities. This event is designed to foster a sense of community and provide a platform for genuine connections among women who share similar values and visions.

Join Ann on This Exclusive Journey

For those who have received an invitation, prepare for an evening of allure and intimate exploration. For those interested in joining future events like this, stay tuned for more opportunities to engage with The Group’s unique social gatherings, where luxury meets liberation.

Stiletto Social’s Launch Party is where the journey begins—step aboard and let us sail into a night of endless possibilities.

[Click Here] to Request Your Invitation

The post Women Step Aboard for an Evening of Elegance and Empowerment first appeared on The Group.

The Group is thrilled to announce the formation of Stiletto Social, a women-centric organization proudly hosted by Ann.

Stiletto Social offers an exclusive haven where sophistication intersects with sapphic intimacy, providing an unparalleled experience designed exclusively for women by women.

Since its inception in 2005, The Group has a rich history of hosting women-only events, gatherings, and soirées. These events began as exclusive dinners for wives, girlfriends, and single women attending on-premise affairs the following night.

Over time, ladies-only segments became integral to The Group’s lavish weekend gatherings, culminating in events like Stiletto Spy Academy, a precursor to the lavish black-tie affair, The Secret Ball in Manhattan. Stiletto Spy Academy began in 2010 and provides attendees with a range of experiences from burlesque and parkour to self-defense and intimate sapphic encounters.

In 2024, The Group returned to its roots with Just For Dinner: Miami Ladies-Only, where the inclusion of a female-female couple marked a significant evolution reflecting changing social dynamics. The overwhelming response to these events saw women from South Florida, Central Florida, and even as far as Arizona traveling to partake in the evening’s camaraderie.

Now, as The Group introduces Stiletto Social, women of all sexual orientations and partnered statuses are welcome to apply. Stiletto Social aims to provide a space where women can come together to celebrate femininity, empowerment, and connection in a supportive and luxurious environment.

“We are excited to launch Stiletto Social as part of The Group’s ongoing commitment to providing exceptional experiences for our members,” said Ann, the co-founder of Just For Dinner by the Group and now Stiletto Social. “This organization represents a celebration of women and their unique experiences, and we look forward to creating unforgettable moments together.”

Stiletto Social invites women to join a community where sophistication meets sapphic intimacy. For more information and to apply for membership, visit www.Stiletto.Social

About The Group: The Group is a premier lifestyle organization dedicated to curating exceptional experiences for its members. With a focus on sophistication, exclusivity, and luxury, The Group offers a range of events and private venues, with services designed to elevate every aspect of its members’ lives.

[Click Here] to read about the Launch Party

The post The Group Announces Stiletto Social first appeared on The Group.

Women take center stage in initiating intimate activities and connections at The Group’s meticulously curated events, following a well-defined vetting process. With confidence and agency, they navigate flirtatious encounters, engage in meaningful conversations, and explore their desires on their own terms. This empowerment fosters a supportive and inclusive atmosphere where women feel at ease to be themselves and embrace their sexuality authentically.

From elegant cocktail parties to intimate dinner soirées, each event offers a unique opportunity for women to connect with like-minded individuals and forge meaningful connections. Here, women are encouraged to take the lead in their interactions, asserting their desires confidently and gracefully. The Group’s ethos revolves around empowering women to embrace their sensuality, celebrate their femininity, and live their lives unapologetically. The Group, since its inception in 2005, regularly hosts ladies-only events as both standalone dinners and parties or as an element of it’s luxury weekend escapes.

Beyond the allure of luxury and exclusivity, The Group is a movement that celebrates female empowerment and sexual autonomy. Through its events and community, The Group provides a safe and welcoming space where women can explore their desires and support one another on their journey of self-discovery.

Essentially, The Group redefines what it means to be a woman in today’s society—a celebration of empowerment, liberation, and sexual autonomy. Women from all walks of life are invited to embrace their desires, celebrate their sexuality, and embark on a journey of empowerment and self-discovery within The Group’s vibrant community.

The post Embracing Empowerment: Women’s Experiences in The Group first appeared on The Group.

Tiffany & Rachel: Pioneers in The Group

Tiffany and Rachel, the dynamic hosts of the Sapphic Swingers podcast, blazed a trail within The Group’s open relationship community. As a female-female couple, their journey navigating open relationships has resonated with a wide audience and inspired others to embark on a similar path.

In their role as podcasters, Tiffany and Rachel have generously shared their stories and experiences, fostering a sense of connection and understanding within The Group. Their openness and positivity helped create an atmosphere where other same-sex female couples and mixed-gender throuples felt not only welcomed but celebrated.

Forging Links to the Broader LGBTQ+ Community

Tiffany and Rachel’s connection to the broader LGBTQ+ community has further enriched The Group’s diverse membership and led to the application by other bisexual and lesbian women, both single and with partners interested in participating in The Group. Tiffany and Rachel were the first to bridge the gap between open relationships and LGBTQ+ experiences, creating a space where everyone’s unique journey is embraced and cherished.

Drawing Parallels with Joel Simkhai’s Insights

Joel Simkhai, the visionary founder of Grindr, a widely recognized LGBTQ+ dating app, offers valuable insights into the everyday challenges different communities face. He astutely points out that, much like The Group, the LGBTQ+ community also seeks upscale and sophisticated environments to connect and build meaningful relationships, but adds that similar experiences, curated for professional gay men, are not as commonplace as he would like them to be.

The universal desire for upscale experiences that cater to diverse backgrounds and orientations underscores the shared needs of these communities.

A Chance Encounter in Key West

An unexpected encounter occurred during the vibrant festivities of Fantasy Fest 2022 in Key West, Florida. While partaking in the festivities, The Group’s founder met a professional male-male couple from Michigan and learned about The Group and its commitment to crafting high-end experiences, most commonly for heterosexual couples.

Their chance discovery led to a meaningful conversation about the unmet needs within the LGBTQ+ community for upscale environments that facilitate connections, trust, and a sense of belonging. This chance encounter further emphasized the importance of fostering inclusive spaces.

With their encouragement, The Group began its investigation and ultimate launch of “Dinner With Men” during Aspen Gay Ski Week in 2024, a compliment to The Group’s occasional Just For Dinner: Women Only soirees.

Conclusion

The pioneering spirit of Tiffany and Rachel, complemented by insights from Joel Simkhai and the serendipitous encounter in Key West, has catalyzed a journey of inclusivity and connection within The Group. Their experiences and dedication to diversity have fostered a nurturing space for same-sex couples, mixed-gender throuples, and individuals from all walks of life. In a world where open relationships and LGBTQ+ identities intersect, The Group stands as a beacon of inclusivity, providing a platform for love, understanding, and connection to flourish. Through shared stories, acceptance, and support, The Group continues to thrive as a diverse and welcoming community where all are invited to explore and celebrate love in its many beautiful forms.

The post Inclusivity: The first (of many) Female-Female Couples in The Group first appeared on The Group.