"She never thought she would be single at 50, and even though she’s outwardly insisting she’s fine about it, deep down she’s humiliated," a source told the tabloid.
"Jen thought she would be settled into a new relationship by now," they added.
Jennifer has been single since splitting with her ex-husband Justin Theroux in 2018.
According to ET, the actress is just fine with the single life and thinks she made the right choice in moving on from Justin.
"Her decision to move forward in life without Justin was one of the most difficult of her life but she now knows for sure, it was the right one. Since they split, her friends believe their plan to move forward in life without one another was the best decision for both of them. Neither of them is pining for each other but instead, finding themselves again," the insider said.
Her most other famous relationship was her marriage to Brad Pitt, who she split from in 2005 after seven years.