A Reminder of How Much Insecure Season 2 Played With Our Feelings

Fresh from her breakup with Lawrence, Issa decides that the best way for her to get over him and their mess is by hooking up with a bunch of different guys. She asks Molly for her help, which she readily provides as any good best friend would, and starts a "ho-tation." With the use of dating apps, she begins to meet several men, though none form truly lasting connections. Her romantic screw-ups are hard to watch but so funny, you can't look away. She does manage to hook up with neighbour Eddie in episode three, though it's up to you if you consider that a win for her.

Season two starts off with Molly deciding to focus on her career rather than her love life. After accidentally getting the pay stub of her white coworker Travis, Molly learns that he makes more money than her, despite not being nearly as good at his job as she is. She starts looking into transferring to the Chicago office of Merrill, Johnson, and Schwartz after a colleague does so and she connects with a visiting lawyer, Quentin (Lil Rel Howery). She also sees a therapist on and off, who attempts to crack through her defences and confront Molly about her obsession with life looking a particular way.

Though Molly briefly dates a man she meets at a club — Lionel, played by Sterling K. Brown — she stops seeing him because she doesn't feel the spark. As she continues to waffle on the decision to transfer offices, she begins spending more time with Quentin, eventually sleeping with him. She admits that Quentin is a great guy who could be good for her, but she decides not to continue seeing him because she can't help but be self-destructive.

As the season opens, Issa and Frieda are working together to get kids at East 41st Street High School interested in their after-school programs. As usual, the kids find the We Got Y'all crew lame and not worth their time. In episode two, it seems like they've gotten a break when the school's vice principal, Mr. Gaines (A. Russell Andrews), offers to help. The problem is, Mr. Gaines is incredibly biased against his Latino students.

Frieda pushes Issa to include his discrimination in their report, but after having fought to keep East 41st included in the program, Issa doesn't want to bring any bad news to her boss. The tension between them bubbles up, and in the end, Issa takes the fall when their boss learns of Gaines's prejudice. Her attempt to make up for his discrimination by hosting separate sessions off campus leaves We Got Y'all open to a lawsuit, and Issa is told that her position is under review. This paves the way for Frieda to get ahead, leading to her promotion as director of student outreach.

Lawrence moves on to Tasha after breaking up with Issa, but their relationship quickly fizzles out by episode three. The opposite of Issa in most ways, Tasha is bubbly and more of a cheerleader for Lawrence. She praises Lawrence for average things and is very obvious about how much she wants him. However, it's clear from the beginning of season two that Tasha wants something serious with Lawrence, while he just isn't ready. She invites him to her family barbecue, which he attends for a few minutes before bailing to hang out with his coworkers.

When Tasha finally calls him after fielding questions from her family about him all day, the two break up with a stormy fight. Tasha tells Lawrence that while she knows they weren't serious, he didn't need to play the role of dutiful boyfriend with her family, only to ghost on her for the rest of the gathering. In a line that many viewers felt deep in their hearts, Tasha tells Lawrence that the worst thing about him is that he swears he's a good guy when he's actually "just another ass."

Kelli spends most of season two throwing out the funniest lines of any character on the series. Somehow she always manages to make any scene 10 times funnier, even if it's just her walking into a room and spotting someone fine to talk to. In the fourth episode, "Hella LA," Kelli, Molly, and Issa attend a day party where each wanders off for their individual adventure. Kelli winds up meeting a guy she refers to as Sweetie, because she can't remember his name. He tags along with the crew to a food joint, where, in a way that's very obvious to everyone else sitting next to them, he starts fingering her under the table. Needless to say, the two definitely connect. Kelli brings him as her date to Derek's birthday party in the next episode, and though we don't hear about him again, we'll always have that food joint.

Tiffany is that friend we all love to hate, and much of her role in season two is to make us do exactly that. Her cruel call-outs are common throughout the season, but it isn't until the final half that we get some peeks into the "perfect life" she's constantly referring to. We already know some indiscretion occurred between the couple, but Tiffany lets it slip that Derek temporarily lived in a hotel before she let him come back home the year before. Derek also has a conversation with Lawrence about a coworker of Tiffany's named Fred that she "had a situation" with. Despite the clues that point to a fractured marriage, the two reveal they're expecting a baby in the finale.

Issa and Lawrence have had some of the most frustrating scenes to watch because of how hardheaded and stubborn the two of them are, but season two sees an official close to the former lovers' story. The season begins with the aftermath of their explosive breakup in season one, with Lawrence dating Tasha and Issa attempting to get back into the dating scene. The two end up sleeping together after Lawrence comes to Issa's place for his mail. They subsequently avoid one another until they're forced to be civil for Derek's birthday party. A heated argument occurs, and the two exchange dangerously low blows. They don't speak again until the final episode, taking place a month later.

In a surprisingly mature move, Issa and Lawrence both apologise for their parts in the erosion of their relationship. They acknowledge how they both messed up and they will always still love one another, and they hug through their tears. As Lawrence turns to leave and say goodbye, we see a vision of the life they could have had — one where they forgive each other, get married, and have a beautiful baby — before Issa snaps out of it. She says goodbye and finally, finally means it.

From the moment we meet Molly's childhood best friend, Dro, we know he's trouble. The two first run into each other at a local cupcake shop, where we also meet Dro's wife, Candice. A few days later, they meet up again at a day party and Dro drops a bombshell on Molly while slow dancing together: he's in an open marriage. The sexual tension is rife between them, and honestly, everyone probably had a moment of wanting to tell Molly to just GO FOR IT! The man is fine. Molly initially resists out of respect for Candice, but soon the two are regularly having sex, and she is clearly catching feelings.

Dro continues to assure Molly that his marriage is indeed open and his wife knows about their relationship, but that doesn't make it easy for her. When Molly and Candice come face to face at Derek's birthday party, Candice doesn't seem to have the slightest clue that Molly is sleeping with her husband. Molly is clearly put off, though she still sneaks off to the bathroom for a quickie with Dro. When it's over, he tells Molly to fix herself up and wait awhile before exiting the bathroom, so he isn't seen leaving with her. The experience seems to shake Molly, who texts Dro saying she can't continue their relationship. But of course, during the last moments of the finale, we see Molly opening the door, wearing lingerie, for none other than Dro.

Issa and Daniel make a lot of missteps in season two, including a hookup that leads to an eye injury. When Issa attempts to add him to her "ho-tation," Daniel's genuine feelings for her put a stop to their messing around, and the two fall out. Later they reconnect, seemingly unable to stay away from each other. Gentrification strikes Issa's apartment complex, and she's given notice to leave. Though both her older brother and Molly offer their places for her to stay in, Daniel is the person she ends up living with. The last minute of the finale shows her rolling up to his door, after spending the night with Molly, and telling him, "I'm sleeping on the couch."