The latest sneak peek shows Issa going on a handful of unsuccessful dates and telling her best friend, Molly (Yvonne Orji), that she is tired of "this dating stuff" and wants her man back.
The eight-episode second season follows the aftermath of Issa's breakup with her ex-boyfriend, Lawrence (Jay Ellis) and her new challenging work assignments that put her new friendship with her colleague, Frieda (Lisa Joyce), to the test. Meanwhile, Molly confronts her future at the law firm and the complex realities of relationships.
"I'm done second-guessing myself," Issa says in the trailer. "I just want to feel good."
In May, ET spoke with Rae on the red carpet at the MTV Movie & TV Awards, where she mentioned that she is feeling "very secure" about the upcoming season.
"I love the stories we're telling, we're filming -- as you know -- and our actors are killing it. Jay [Ellis], Yvonne [Orji], they're killing it," Rae gushed. "Me and the writers put in work this season. We feel like we're really staying true to life."
Insecure returns Sunday, July 23 on HBO.
For more on what Rae had to say about season two, watch below.