Debra Lynette Robinson was celebrating Sismas, an annual holiday event honoring sisterhood among women, with 60 of her friends on Dec. 9, 2023. One of the women, Crystal Etienne, hosted the event at her Upper Brookville, N.Y., home, with Ms. Robinson’s best friend, Simone I. Smith, the founder of the event.

The group excitedly caught up while they sipped cocktails, Ms. Robinson said. “The room was full of joy, and we were dancing and laughing when Simone suddenly pulled me aside and told me she needed to talk to me,” she said.

Ms. Smith, a jewelry designer who is married to the rapper LL Cool J, led her to the front lawn. When she heard the R&B song “Good Luck Charm” by Jagged Edge playing over a speaker, Ms. Robinson knew this was no ordinary conversation. “My heart stopped,” she said. “It’s mine and Andre’s favorite song,” referring to her boyfriend, Andre Galloway.

Then, she noticed large glowing white letters on the lawn spelling out, “Marry Me,” and said she started shaking and broke out in tears. “Andre pulled up in a golf cart, walked over, and told me, ‘Everyone has a season, and this is our season,’” she said.

As Ms. Robinson’s fellow “sisters” watched the scene unfold, she said, “yes,” and they broke out in cheers and applause.

Mr. Galloway, 57, had orchestrated the proposal for several months with the help of Ms. Robinson’s friends. “Sismas is so meaningful to Debra, and I didn’t think there was a better time to do it than when she’s surrounded by the women who are everything to her,” he said.