Still Going Strong: ‘90 Day Fiance’ Stars Robert and Anny’s Relationship Timeline

2019

After a chance encounter on Facebook, Robert booked a cruise that stopped in the Dominican Republic for one day. He would end up proposing to Anny just eight hours after meeting her in person.

“Anny and I only spent eight hours together,” the Florida native told producers in a 2019 confessional. “But it was the best eight hours of my life. So right then and there, I was like, ‘I have to have this shorty,’ so I asked her to marry me.’”

September 2019

While Anny imagined a lavish lifestyle upon her arrival in the Sunshine State, she was shocked when Robert took her thrift shopping instead. Already a father of five, Robert lived on a budget and couldn’t live up to his previous promises.

Anny also bumped heads with Stephanie Woodcock — the grandmother of Robert’s son from a previous relationship, Bryson. During their first meeting, the adult film star intrusively asked Anny what type of birth control she was on and asked her if she wanted more children. She would also later offer Anny $15,000 to leave Robert and return to her home in the Dominican Republic.

Despite the drama, the pair tied the knot during season 7, with their wedding playing out during a February 2020 episode.

July 2020

Anny and Robert welcomed their first child together, Brenda Aaliyah, on July 28, 2020.

September 2021

The reality TV couple announced they were expecting their second child together in April 2021. Dubbing baby No. 2 as their “quarantine baby”, an episode of 90 Day Fiancé: Pillow Talk featured their gender reveal, where they announced they would be welcoming a son. 

On September 8, 2021, their baby boy — named Adriel Hassan — made his way into the world. Weighing in at 9 lbs 3 oz, Robert gushed about his wife via his Instagram Stories, “Much love and respect to my wife who’s the true warrior.” 

April 2022

Sadly, seven months after the arrival of Adriel, Anny and Robert would reveal their son passed away after undergoing a medical procedure.

“This was the last pic an hour before my son’s surgery,” Anny wrote via Instagram on Saturday, April 23, in Spanish, which has been translated to English. “Life is unfair, I just wanted my kids.”

April 2022

On April 28, Robert and Anny laid their precious son to rest during a funeral. Anny reflected on the burial in a message via Instagram.

“Today was one of the worst days of my life,” the reality TV star, 32, wrote in Spanish via Instagram on Wednesday, April 27, which has been translated to English. “[I] had to say ‘goodbye’ to my so. Never in my life was I so ready to bury my son. It’s so painful and hard. I feel my heart being squeezed out of the pain I have, and it knows I can’t change anything to get back to my son. My angel Adriel. But it’s not ‘goodbye,’ but ‘I’ll see you again someday.’ I love you forever, my life.”

May 2022

In a bittersweet sequence of events, Robert and Anny reached an important milestone in their marriage just one month after suffering the heartbreaking loss of their son. In Touch confirmed the couple bought their first house together in Florida on May 4 for  $335,000.

April 2023

One year after Adriel’s passing, Anny shared a sweet tribute commemorating her 7-month-old son.

“A day like today, they gave the worst news that changed my life forever,” she wrote via Instagram on April 20, 2023, alongside a photo cuddling the little one. “Losing my son has been too painful, hard to understand because I had to live it and very few people understand me.”

The 90 Day Fiancé star continued, “A child is like half of our heart, and I do not wish my worst enemy to go through this because all material things in this life can be recovered but the loss of a family member … never.”

July 2024

Robert and Anny announced they were expecting their third child together nearly three years after the death of Adriel. “Super excited and emotion [sic],” Anny wrote alongside the announcement, which was translated from Spanish. “I didn’t think I would have another child again but thanks to God and life here I come … thankful great mind … It’s a boy.”

November 2024

Baby No. 3 arrived! Anny and Robert announced the birth of their son Eliel on November 6, 2024. “He’s here. Nine pounds, seven ounces,” Robert shared via his Instagram Stories at the time. “What a great day, happy birthday son.”