HBO’s Insecure: The Main Characters, Ranked By Likability

HBO’s Insecure is an award-winning show that stands out as one of the few that do representation right. Not only that, but it also introduces a wide array of complex characters, each of them flawed in some way or another. Their insecurities especially shine through in romantic relationships and of course, friendships. After all, the show is, at its core, a story about two best friends, Issa and Molly.

Insecure does a great job at showing that the world is simply not black-and-white. Take Issa’s and Lawrence’s relationship, for example. While betraying your partner is a big no-no, can anybody really judge Issa considering the fact that Lawrence made no effort to keep the relationship afloat? There are countless of these kinds of moral dilemmas in the show and characters who are better at navigating interpersonal struggles rank higher when it comes to how likable they are.

10 Dro

He might be good-looking and charming, but no character has as little regard for other people as Dro. From the get-go, Molly didn’t feel comfortable with their little arrangement, yet he pushed her and manipulated her into coming back for more.

When Molly finally drew some boundaries and told him to give her back her keys, he made a whole scene. The scene at the baby shower suggests that Dro doesn’t care one bit about Molly, even though he definitely made it seem otherwise for a little while.

9 Molly

Despite her success, intelligence, and fashion sense, Molly is a character who is really hard to like. She’s mean, needy, and frustrated. All those frustrations are slowly, but surely turning into resentment. She’s also incredibly defensive; so much so that she couldn’t even handle seeing a therapist at first.

That being said, Molly has a lot to offer. She always helps her friends out, she’s loyal, honest, and thoughtful. She could end up with a lot of characters, but the truth is that she needs to be content on her own first. Hopefully, she will grow in season 5, but a character that stubborn is unlikely to change within a span of one season.

8 Condola

Unlike Issa and Molly, Condola seems to have her life in order. At first, there were no reasons not to like her. After all, she was friendly, mature, and transparent. But when she told Lawrence she was pregnant, fans quickly connected some dots and realized she’s not as innocent as she seems.

Condola told Lawrence right away that she wants a family, not another marriage. Meanwhile, he was sure that they were being careful, which suggests they had a conversation about safe sex. She instantly lost face in the eyes of the show’s fans, even though she seems sweeter than honey at first glance.

7 Tiffany

Tiffany is the one friend who doesn’t seem that invested in the group. She’s not a part of the fake Instagram account that Issa, Molly, and Kelli have and she didn’t turn to them to organize her baby shower.

Tiffany is a bit of a mystery. At the end of season 4, she finally showed her vulnerable side, which instantly made her a more likable character.

6 Nathan

Fans welcomed the good-looking newcomer with open arms. Issa and he had one of the best dates in the show. He inspired Issa to think bigger and to eventually quit her job.

Nathan lost a lot of likability points when he suddenly ghosted Issa and left her wondering what had happened. Fans got attached to the resident sad boy, too, and the wounds he left still haven’t healed.

5 Daniel

Even though cheating is unforgivable, it’s not hard to sympathize with Issa who succumbed to Daniel King’s advances. After all, the charming producer was her “what if guy”.

He didn’t even know the whole extent of Issa’s relationship situation in season 1, which led to that uncomfortable confrontation at Issa’s fundraiser. Later on, when Issa was in financial trouble, he let her stay on his couch anyway.

4 Issa

There’s no denying that Issa is a bit of a mess, but unlike Molly, she learns from her past mistakes and owns up to them. She started out as the one who has it all figured out but underwent a massive transformation during which she lost everything she once took for granted.

Now, she’s finally living up to her potential as a creative type who has a secret talent for spitting bars. She’s also got a lot of potential romantic partners lined up. Ideally, she will stay single and keep working on herself when the show wraps up.

3 Lawrence

Insecure is a show filled with nuggets of wisdom about dating life. As Issa said in the wake of her break up with Lawrence, she wanted her man back. No wonder, his glow-up was unreal! He went from being a complacent couch potato who neglected his girl to the most dapper man in town.

He was one of the most grounded and honest characters in the show. He doesn’t have it in him to manipulate people or to bend them to his own will. The only person he led on was Tasha, and even then, he didn’t do so purposefully.

2 Tasha

Tasha, Lawrence’s rebound girl, deserved so much better than to have an emotionally unavailable man come into her life and use her to have his ego stroked. It was hard not to feel sorry for her.

Unlike Issa, she believed in Lawrence and she wanted so desperately to be loved that she settled for him coming over for the weekend and never taking her out on a real date. Luckily, Tasha soon came to her senses and realized that Lawrence is in no way capable of giving her what she needs and deserves.

1 Kelli

This hilarious lady is always bursting with energy and bringing good vibes to the group. Her behavior is often embarrassing, but she owns it. In her own words, “the Lord knows that she gets turnt”. She doesn’t concern herself with romantic relationships like the rest of Insecure characters.

Hopefully, the last season will give Kelli more substance rather than just have her as the show’s main comedic relief. She deserves as much: she is the most likable character on Insecure.

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