Brandy’s Dating History, Called-Off Engagement And Bond With Daughter Amid Concert Exit Row

R&B singer, Brandy is currently making headlines for walking off stage during a concert in Chicago on October 18, 2025. After a significant buzz around it, she explained the reason was her health issues. Brandy’s mid-performance exit was due to “dehydration and feelings of wanting to faint”, according to a statement she posted online. The incident happened during a show at the United Center for The Boy Is Mine tour. Amid the drama around her professional life, here’s a look into her private life, particularly her called off engagement with Ryan Press and her daughter, Sy’rai Smith.

Brandy and Ryan Press’ whirlwind romance

The relationship between singer Brandy and music executive Ryan Press lasted approximately two years, from late 2011 to early 2014. The ex-couple also got engaged; however, that was ultimately called off. Brandy and Ryan Press’ romance began in 2011, and they went public on New Year’s Eve of the same year, cuddling at a Las Vegas party. Brandy later stated she had given up on love before meeting Ryan; however, her views changed after meeting him.

Within a year, Brandy and Ryan Press decided to take their relationship to the next level. The couple got engaged around the Christmas holidays in 2012. Brandy confirmed the news, with a source close to her telling Us Weekly that the pair was ‘thrilled and happy’. Brandy told PEOPLE that Ryan “just loves me for who I am,” and that the proposal was a spontaneous thing. Despite such a strong bond between Brandy and Ryan, they eventually split. Know what the reason was for the end of their relationship.

Why was Brandy and Ryan Press’ engagement called off?

Brandy and Ryan Press called off their engagement in 2014 after they decided to take a step back and reevaluate the relationship. A representative for Brandy emphasised that the split was amicable, with the pair remaining friends. Brandy clarified that she and Ryan “just grew in different directions.” At the time of the breakup, Brandy’s rep stated that the singer was going through a period of change, mentioning her 35th birthday and the desire to become her own woman.

Brandy’s representative also shared that Brandy “wants to be married and have more kids but she is working on so many other things right now.” But since then, she had not dated anyone, as per reports. Before her brief romance with Ryan Press, Brandy dated another man, music producer, Robert ‘Big Bert’ Smith. They are also parents to a daughter named Sy’rai Smith. Brandy and Robert began dating around mid-2001, while working on Brandy’s Full Moon album. In the same year, they held a private, non-legal ceremony and pretended to get married.

Did Brandy and Robert Smith fake a marriage to avoid backlash around the birth of their daughter?

In February 2002, the couple publicly announced that they had quietly married the previous summer and that Brandy was pregnant. In June of the same year, their daughter, Sy’rai Iman Smith, was born. The pregnancy and birth were documented on the MTV reality series Brandy: Special Delivery. About a year after Sy’rai’s birth, Brandy and Smith officially announced their separation. In 2004, Robert publicly revealed on a radio show that he and Brandy had never been legally married; however, Brandy contested the statement. Amid all the chaos, Brandy and her daughter remained close and are each other’s ‘best friends’.

What are your thoughts on Brady’s failed relationships with Ryan Press and Robert Smith? Let us know.

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