Tristan Schukraft and Jennifer Coolidge attend the opening night party at The Tryst Puerto Vallarta on April 25, 2025 in Puerto Vallarta, Mexico.
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Jennifer Coolidge Almost ‘Got Lucky’ Hanging Out with the Gays at The Tryst Puerto Vallarta

Jennifer Coolidge nearly had a memorable night at the grand opening of The Tryst, Puerto Vallarta’s new luxury boutique hotel catering to LGBTQ+ travelers.

Photo: Presley Ann/Getty Images for Tryst Hotels

Jennifer Coolidge nearly had a memorable night at the grand opening of The Tryst, Puerto Vallarta’s new luxury boutique hotel catering to LGBTQ+ travelers. The event, held on Friday, April 25, 2025, was a star-studded affair that attracted numerous celebrities, including Coolidge, who shared her experiences and sentiments about the LGBTQ+ community during the festivities.

A Night of Glamour and Celebration

The opening night kicked off with a red carpet event hosted by Matt Rogers, setting the tone for an evening of elegance and excitement. Demi Lovato made a surprise appearance, performing her hit song “Cool for the Summer” on the hotel’s rooftop, energizing the crowd as DJ Leland spun tracks into the night. Other notable attendees included Erika Jayne, Cynthia Bailey, Sonja Morgan, Antoni Porowski, Julia Fox, Laverne Cox, Chrishell Stause, Sam Asghari, TS Madison, and Kate del Castillo, among others.

The Tryst, founded by entrepreneur Tristan Schukraft, aims to provide a space where LGBTQ+ individuals can feel celebrated and accepted. Schukraft emphasized the importance of such inclusive environments, stating that they allow people to be themselves without judgment and to connect with like-minded individuals.

 

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Jennifer Coolidge’s Reflections on LGBTQ+ Community

During the event, Jennifer Coolidge took a moment to reflect on her longstanding connection with the LGBTQ+ community. She expressed that her affinity for gay men and women began at a young age, noting that she was naturally drawn to them without being consciously aware of their sexual orientations. Coolidge described these early friendships as a mutual attraction, where she and her LGBTQ+ friends simply enjoyed each other’s company without labels or judgments.

Coolidge also shared her thoughts on being an ally to the LGBTQ+ community. She emphasized the importance of spending time with LGBTQ+ individuals, enjoying their company, and participating in events that celebrate their identities. Her presence at The Tryst’s opening was a testament to her commitment to supporting and uplifting the community.

 

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A Lighthearted Moment: “Almost Got Lucky”

In a playful exchange during the event, Coolidge joked about “almost getting lucky,” sparking laughter among those around her. While she kept the details lighthearted and vague, her comment added a touch of humor to the evening’s festivities. This moment highlighted Coolidge’s ability to connect with others through humor and her genuine enjoyment of the celebration.

 

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The Tryst: A New Haven for LGBTQ+ Travelers

The Tryst is more than just a hotel; it’s a sanctuary designed with the LGBTQ+ community in mind. Located in Puerto Vallarta’s Zona Romántica, the hotel offers 55 elegantly designed rooms that blend minimalist elegance with Mexican flair. Each room features private balconies, ultra-soft bedding, intimate mood lighting, Egyptian cotton towels, Grown Alchemist toiletries, and a mini bar stocked with favorites. The hotel also boasts a rooftop pool and bar, providing panoramic views of the city and the Pacific Ocean.

Beyond its luxurious accommodations, The Tryst fosters a vibrant social scene. Weekly events include the “wettest drag brunch in the world,” hosted by Pelayo in the hotel’s Courtyard, featuring a rotating lineup of drag queens, bottomless mimosas, and an international brunch menu. The rooftop pool and 8th-floor cocktail lounge, Ocho, transform into the ultimate party destination, featuring world-famous DJs, signature cocktails, and iconic Tryst gogo dancers.

The success of The Tryst’s grand opening marks the beginning of a new chapter in LGBTQ+ luxury travel. Following the Puerto Vallarta location, Schukraft plans to expand The Tryst brand with new properties in San Juan, Puerto Rico, and Fire Island, New York, in 2025. These upcoming hotels aim to offer upscale, inclusive experiences for guests seeking high-end accommodations with a vibrant, social atmosphere.

For Jennifer Coolidge, her appearance at The Tryst’s opening was more than just a red carpet moment; it was a reflection of her enduring support for the LGBTQ+ community and her appreciation for the joy and authenticity it brings. Her presence and words resonated with many, reinforcing the importance of spaces where individuals can be their true selves without fear of judgment.

As The Tryst continues to welcome guests and host events that celebrate LGBTQ+ culture, it stands as a testament to the power of inclusivity, community, and the shared human experience.

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