In the aftermath of recurring and traumatic dreams about his now ex, Ladonna, Carl accepts an olive branch and an invitation from Elliot celebrating his new engagement to Ladonna. Carl has officially proclaimed he's 'done with sisters', so to demonstrate (and overcompensate) he brings one of his new prospects, Amanda to the event. Meanwhile, Carl's daughter, Corinne, is excited to introduce HER NEW BOYFRIEND, ERIC and enthusiastically brings him to the affair to introduce him to Carl's 'tribe'. He's white. Carl isn't pleased and takes it personally. After all, don't daughters always choose men just like their fathers?
Carl"s lingering "nightmares" of reconciling with Ladonna persist. - leading him to confide these dreams to James (Dick) Black who then leaks it to Oscar, Kent, Kevin and Mark Christopher at the DEBONAIR CIGAR LOUNGE. The consensus? Carl needs to meet with a professional. Enter the beautiful and very capable "Dr. Abigail Whitmore" to rescue Carl from this persistent hell space and to guide him back to the 'sisters' after swearing them out of his life. Because of Dr Abigail's beguiling beauty and stunning intelligence, it takes Carl some time to grasp the fact that it's therapy and not another opportunity to "smash".
After the "Amanda" travesty in the season opener and a successful therapy encounter with Dr. Abigail, Carl decides to have a go with black women again. The wonderful Latonya Black has his interest as does another beauty named Christine. Carl has found his sea legs with several dating options with harrowing results. Christine surprises Carl by inviting one of her dear friends who turns out to be Carl's ex, Trisha who arrives with her husband Tony. Drama, shenanigans and repercussions ensue.
Carl is invited to hear Christine sing at a newest and hottest Showcase spot in LA. It's the newest place to be on Friday Nights. Upon arrival, Carl runs into his friend, comic Dino Shorte. Their conversation ends in contention as Dino challenges Carl to do 5 minutes of stand up comedy the following week for A huge wad of cash. Not to be outdone, Carl accepts the challenge but has no idea what to do, even as he fronts that anyone can tell jokes. Carl is a trained thespian. He can do this. Panicked, Carl seeks to find somebody to give him a quick tutorial on how to "bring the funny". Meanwhile, Ajai and Tony are on their last relationship moments as Ajai finally takes to the comedy stage with some surprises up her sleeve.
Carl and Latonya have planned a casual coffee date. Carl arrives early at the establishment where he encounters Hollywood actors Miguel, Vanessa and Tico and from this seemingly benign encounter comes high drama and confrontation with two GEN Z young ladies who fail to give Carl the respect he feels that he deserves.
After a series of miscues, miscommunication and mishaps, Carl is thrust into a time of a reflective crossroads; a time where he will have to FACE HIMSELF and his past. Carl's future and his happiness counts on it. Ladonna, Elliot and Latonya are all entanglements which must be expeditiously resolved.