Sterling Shepard proposes to girlfriend Carolyn Estephany 2 years after finalizing divorce with supermodel Chanel Iman

Sterling Shepard is ready to turn a new chapter in his life with model and influencer Carolyn Estephany. The two went public with their relationship shortly before the 2023 NFL season. Sterling announced on June 27 that he has proposed to Carolyn, and she has said, "Yes!"

The Tampa Bay Buccaneers WR popped the big question at Amanyara, a luxury beach resort located on the secluded shores of Providenciales in Turks & Caicos, which is certainly the perfect setting for such an occasion.

The proposal comes just two years after Shepard and his ex-wife Chanel Iman divorced due to "irreconcilable differences" in the marriage.

Shepard and Estephany celebrated their second anniversary in April 2025, with Carolyn posting a heartfelt tribute on Instagram. Shepard had commented on the post:

“I love you more mama."

Shepard's comment on Carolyn's Instagram post. (Photo via IG/ @CarolynEstephany)

The couple also made quite the stylish splash at the 2025 Masters in Augusta, Georgia. Carolyn shared photos from their outing on Instagram, captioning it:

“First time at The Masters go sports!”

She wore a crisp white long-sleeve with a red diamond logo, while Sterling rocked a dark blue polo with a white collar and a light blue pocket.

Shepard and Chanel Iman tied the knot in 2018. They share two daughters, Cali and Cassie, who they co-parent since separating in 2021.

Shepard also briefly dated Shaniece Hairston, the daughter of Basketball Wives star Evelyn Lozada, in late 2022. On the other hand, Carolyn Estephany was married before as well. She has a son named Lion from that relationship.

Sterling Shepard was drafted by the New York Giants in the 2nd round (40th overall) of the 2016 NFL draft after a standout college career at Oklahoma. He spent the bulk of his career in New York and joined the Bucs in 2024.

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NFL stars' partners reacted to Sterling Shepard and Carolyn Estephany's engagement news

The NFL 'WAGS' community reacted to the news pretty quickly. Hannah Brooke, who is engaged to New York Jets player Jermaine Johnson, wrote happily:

“YESSSS I AM SO HAPPY TO SEE THIS. Congratulations you two.”

Lauren Wood, the mother of Odell Beckham Jr.’s child, also shared her happiness by saying:

“Awwwyyyy. Congrats.”

Emily Engram, wife of Denver Broncos player Evan Engram, wrote:

“CONGRATS LOVE BIRDS❤️❤️❤️."

Source: (Via Instagram/ @Sterling Shepard)

Jameis Winston’s wife, Breion Allen Winston, also joined in on the fun with the comment:

“Ahhhh Congratulations you guys!”

We can rest assured that the couple's marriage will be a grand affair whenever it takes place.