Since her public meltdown over a decade ago, the star has been under a legal guardianship in which a conservator -- generally her father Jamie -- oversees her finances and everyday life.
According to makeup artist Maxi, the 38-year-old pop star would have possibly married and had a child with her boyfriend Sam Asghari if the conservatorship didn't keep her from doing so.
Spears has been dating Asghari since 2016. She shares two sons with ex-husband Kevin Federline: Sean, 15, and Jayden, 14.
"I can tell you what they’re still controlling to this day is whether she has a baby or not, whether she gets married or not, who her friends are, and those are some big things,” said the makeup artist during an episode of the "Calababes Podcast," per Us Weekly.
They added: "We’re talking about some 'Handmaid’s Tale'-type things to keep her from having a baby. Like, we’re talking … I can’t detail it and I’m not gonna specifically say, but I will say for sure, she would’ve had a baby by now. She would’ve probably been married to [boyfriend] Sam [Asghari, 26] by now. She would have groups of friends around her."
Reps for Spears and her father did not immediately respond to Fox News' request for comment.
While Maxi finds the situation to be "sad," they noted that Spears now "has more control over her social media."
Jamie made things difficult for his daughter and his beau in the past as well, Maxi claimed.
"At that time, she was under the conservatorship basically controlled by the father, but even at that time she was able to bring in Sam as a boyfriend," they claimed. "Now Sam was put through hell by the father and I can’t detail all the things that he went through, but he went through a lot of hell to even be with her."
Tensions appear to be high between the "Lucky" singer and her father, as she's reportedly been pushing back against the conservatorship in court as of late.
This summer, it was reported that Spears is "strongly opposed" to her father resuming duties as her sole conservator, while it was later reported that she has requested that a trust company take over such duties.
In August, the legal guardianship was extended into 2021.