From Breakup Rumors to Yacht Celebrations, Here’s All You Need to Know About Deshaun Watson and Jilly Anais’ Relationship Timeline

Deshaun Watson just got engaged to his longtime girlfriend, Jilly Anais. The Cleveland Browns QB’s fiancée posted a picture on her Instagram story with the caption, “Mrs. Watson loading…” to share the news. Now, many may wonder who Anais is following the reveal. Well, don’t worry — we’ve got you covered with all the details about her and Watson’s dating history below.

Anais is best known as a social media influencer and rising pop singer. She boasts over 2 million followers on Instagram and has released several singles, along with music videos to accompany them. Anais is also a model and an author, having penned a successful cookbook. She even has her own line of perfume and appeared in the most recent season of Selling Sunset. 

But when did Anais start dating Watson? Back in 2019, the then-Texans quarterback shot his shot via DMs. Soon after, they went on their first date — a morning workout session at a yoga studio. The two hit it off, had dinner later that day, and have been together ever since.

Earlier this year, though, it seemed like the two were headed for a breakup. Watson shared a TikTok post not too long ago, where he talked about loving someone but letting them go if they disrupt your peace. Many assumed he was referring to Anais.

However, the star QB quickly shut down the speculation a week later, posting intimate photos with her on a yacht to celebrate her birthday. So, it’s clear that the TikTok wasn’t about Anais.

Jilly Anais comments under her Birthday post from Deshaun Watson pic.twitter.com/dN9S1NgOeo

— Depressed Eagles Fan (@nfl_rocky) January 2, 2025

Furthermore, the couple continues to post about each other online. They’ve been together for years and have become deeply intertwined in each other’s lives. Anais has also stood by Watson through the controversy surrounding his sexual assault cases.

 

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In March 2021, a woman filed a complaint against Watson, claiming that he had sexually harassed her during a session. A month later, 22 additional women came forward and claimed the same.

The claims continued and even two more cases were filed last summer. But in December 2024, the NFL officially closed the case and stated that there was a lack of evidence to hold up the claims. The worst of Watson’s punishments was an 11-game suspension he had to serve in 2022. 

Despite the controversy, Anais has remained with Watson. It may come as a surprise to some, but the two seem genuinely happy, often sharing their adventures and escapades on social media. Now, they are celebrating their engagement. It’ll be a nice side adventure for Watson to focus on while he continues rehabbing from a double Achilles tear.