Cleveland Browns quarterback Deshaun Watson recently announced his engagement to longtime girlfriend Jilly Anais, sharing the news on Instagram with a series of photos from a beachside proposal. The couple, both 29, began dating in 2019, and Anais, a singer, actress, and cookbook author, has stood by Watson through various challenges, including multiple sexual misconduct allegations.
Congrats! Browns star QB Deshaun Watson is now engaged to his girlfriend Jilly Anais.
Such a happy couple ❤️🥹 pic.twitter.com/DcrVUTMTCZ
— Dov Kleiman (@NFL_DovKleiman) March 16, 2025
Watson’s career has been marred by controversy, with over two dozen women accusing him of sexual assault and inappropriate conduct during massage sessions between 2017 and 2020. These allegations led to an 11-game suspension in 2022 and a $5 million fine. While two Texas grand juries declined to pursue criminal charges, Watson settled most of the civil lawsuits.
In addition to legal troubles, Watson has faced on-field challenges, including injuries that have limited his play to only 19 games since joining the Browns in 2022. He is currently recovering from a re-ruptured Achilles tendon, potentially sidelining him for the 2024 season.
In What Has to Be Described as a Masterclass of Playing the Long Game; After 6 Years of Dating, Multiple Admissions of Cheating, Double Digit Lawsuits and No 300 Yards Games, Deshaun Watson Finally Proposes to His GF Jilly Anais (Engagement Photos) https://t.co/xgVtdOs4O8
— Robert Littal BSO (@BSO) March 16, 2025
Despite years of criticism following the allegations, most social media reactions to Deshaun Watson’s engagement were positive, with many fans congratulating him and Jilly Anais on their next chapter. However, there was no shortage of negativity, as some users expressed skepticism about the timing and sincerity of the proposal. One comment read, “In what has to be described as a masterclass of playing the long game; after 6 years of dating, multiple admissions of cheating, double-digit lawsuits and no 300-yard games, Deshaun Watson finally proposes to his GF Jilly Anais.” Others were outright harsh, with one user remarking, “Boy is she dumb… he’s a serial cheater!”
Deshaun Watson is engaged.
Deshaun Watson is engaged. 💍
(📸: @deshaunwatson) pic.twitter.com/zfAU8iQxKV
— theScore (@theScore) March 16, 2025
Despite years of criticism following the allegations, most social media reactions to Deshaun Watson’s engagement were positive, with many fans congratulating him and Jilly Anais on their next chapter. However, there was no shortage of negativity, as some users expressed skepticism about the timing and sincerity of the proposal. One comment read, “In what has to be described as a masterclass of playing the long game; after 6 years of dating, multiple admissions of cheating, double-digit lawsuits and no 300-yard games, Deshaun Watson finally proposes to his GF Jilly Anais.” Others were outright harsh, with one user remarking, “Boy is she dumb… he’s a serial cheater!”
If you want a more in-depth look at some of the meanest reactions, check out these X (formerly Twitter) posts to see what I can’t put in this story-some people didn’t hold back on this topic.
Deshaun Watson gets engaged to longtime girlfriend Jilly Anais https://t.co/gwysUcg62w pic.twitter.com/hbKg58hfgT
— New York Post (@nypost) March 16, 2025
Despite the mixed public sentiment, Watson and Anais appear committed to moving forward together. As Watson continues his rehabilitation, the couple may use this period to plan their wedding, embracing a new chapter amidst ongoing challenges.
