Gabby Windey knows how to make a statement, and she did just that at Cosmopolitan’s inaugural Love Ball, hosted in partnership with Bumble. Held at The Standard, High Line to celebrate Cosmo’s Love Issue, the event encouraged guests to embrace a sexy dress code—and the former Bachelorette turned Traitors star did not disappoint.
For the occasion, Gabby opted for a daring take on the naked dress trend, wearing a sheer black slip that highlighted her effortless confidence. The bold ensemble was complemented by a ruffled black jacket, strategically placed to add an element of intrigue while keeping the look sophisticated. Her choice perfectly embodied the event’s theme: embracing love, confidence, and fearless self-expression.
Gabby wasn’t alone in celebrating the night. Her girlfriend, comedian and writer Robby Hoffman, was also in attendance, as seen in intimate snaps shared on Instagram. One candid shot posted by Jess Neises captured a sweet moment between the couple, while another shared by model and activist Lauren Chan showcased a warm embrace.
Beyond her show-stopping fashion moment, Gabby has been opening up about her evolving perspective on love and relationships. In a recent interview with The Cut, she expressed gratitude for her relationship with Robby, sharing how therapy and personal growth have helped her embrace love more fully. “I’m so grateful for my relationship with Robby and that I’m getting over the things that would keep me from being with her,” she said, highlighting the role of therapy and self-reflection in her journey.
As for Valentine’s Day, Gabby revealed to People that she and Robby make a conscious effort to stay connected despite their busy schedules. Their routine includes morning coffee together, tackling word games like Wordle and Connections, and maintaining a no-phone policy during meals. “We’re lucky that even if she has a show at 8 p.m., we’ll have a 6 p.m. dinner. And no phones. I’m terrified of being in the relationship where we’re just scrolling and watching TV and not paying attention to each other,” she explained.
With her fearless style and heartfelt approach to love, Gabby Windey continues to be a standout both on and off the red carpet. Her look at the Love Ball wasn’t just about fashion—it was a reflection of her confidence, her personal evolution, and the love she’s celebrating every day.