See Issa Rae Flub Life, Love in Endearing 'Insecure' Trailer

Acclaimed HBO comedy returns for second season this July

Issa Rae stumbles through a series of bad dates and everyday awkwardness in the endearing new trailer for Season Two of 'Insecure.'

Issa Rae stumbles through bad dates and everyday awkwardness in the new trailer for Season Two of Insecure. The comedy returns to HBO July 23rd at 10:30 p.m. ET.

The clip opens with Rae – who plays a fictionalized version of herself – going on a series of bad dates marked by boring questions, spilled drinks and a make-out attempt that ends with an accidental head-butt. But amidst random hookups and enlisting her best friend Molly (Yvonne Orji) to coach her through her "hoe phase," Issa also finds herself sending nudes to her ex Lawrence (Jay Ellis) – and getting caught in the process.

While the Insecure Season Two trailer is packed with plenty of rom-com ridiculousness, it also teases the show's astute take on racism and sexism. When Molly, a corporate lawyer, finds out that a white co-worker makes more than her, their friend Kelli (new series regular Natasha Rothwell) quips, "That's why I make sure my white clients get less on their tax returns – it's reparations. Real talk, don't tell nobody because I'm gonna go to full jail."

Rae co-created Insecure with Larry Wilmore. The show's critically acclaimed first season earned Rae a Golden Globe Nomination for Best Performance by an Actress in a TV Series – Musical or Comedy.