Every son on I Love a Mama’s Boy promises his partner comes first. Four seasons on, one son finally broke free, one walked out mid-fight, and two never made it out of the front door. With Season 5 still unconfirmed, according to reports, which of these men is actually free? Five sons, ranked from freest to most trapped.
Matt McAdams: The Son Who Finally Got Out
Matt’s road to freedom was the longest on the show: four years with Kim inside his mother Kelly’s world, including a stretch living in Kelly’s house after the couple’s apartment burned down, then Brittany Taylor and the show’s messiest breakup — Matt later admitted seeing other women, confessing he “took a coward’s way out.”
Now Matt has sat in a podcast studio beside Kelly and his girlfriend Devon, all three smiling, and posted that he and Devon were “so excited for the future” and “mom’s ready for the ride.” The woman who once refused to share her son is now his cheerleader. Matt takes the top spot — but will Kelly’s support survive the first real disagreement?
Roberto Hernandez: The Walkout That Changed Everything
Roberto’s freedom came at a brutal price. His mother Nancy convinced him to demand a paternity test on his own daughter Kimi. The result came back 99.99 percent his — yet Nancy reportedly asked why it could not be 100 percent. Kristy’s reply became iconic: “Who is she that I have to prove to her?” Then she walked out, and Roberto followed his wife out the door instead of defending his mother.
According to reports, the couple later distanced themselves from Nancy and are still together. Roberto ranks second: he made the hardest choice on the show, but the test is a scar that never fully fades.
Shekeb and Josh: The Sons Who Never Left
Shekeb Sekander never got his move-out moment. Laila spoon-fed him breakfast, shut down every serious talk with “Momma gonna die,” and once brought Yussra, her pick for Shekeb, to dinner as sabotage. Emily asked for a $40,000 ring and got a $500 promise ring, with Laila hidden in the bushes to watch. When Shekeb finally shared plans to move out, Emily got kicked out instead. According to reports, the couple have since split for good.
YOU MAY LIKEThe Women Who Walked Away: 4 Exes Who Escaped I Love a Mama’s BoyJosh McAloon’s case is even more extreme: he never lived apart from his mother Tina in 12 years of marriage to Janelle, and when Janelle bought a Florida house with no room for Tina, Tina answered, “I’m his mother! I came first.” Shekeb lost the relationship; Josh never got the chance to build one outside his mother’s shadow. The two tie for last — the sons who never left.
Shahid: The New Guard Still Sharing Everything
Season 4’s Shahid is the warning sign for what comes next. He and his mother Dia share finances so closely that he said, “We used to be one.” Shopping for Nylah’s ring, he admitted he feared his mother finding out: “My mom gave me a budget of like $25 today.” Dia, meanwhile, judged Nylah on a first impression and questioned her intentions toward his money. Shahid sits just above the bottom: every early sign points the same way. If Season 5 arrives, he is either the next Matt — or the next Shekeb.
Verdict: Matt got out, Roberto walked out, Shahid is still deciding, and Shekeb and Josh never left. Who is the most trapped son in Mama’s Boy history — Shekeb, Josh, or is Shahid headed for the same trap? Has Matt really earned his freedom, or is Kelly just better at hiding the strings? Pick a side below.
