Issa Rae is a genius and an absolute star for giving us Insecure, one of the best shows on HBO. Comedy, excellent, lovable characters, drama, scandal, friendship and romance— a 10/10 show. And what’s even better than watching the show? Talking about it!
Analysing the characters and dogging them for their bad behaviour (looking at you Molly) is one of the best parts of experiencing Insecure.
The love interests on the show are gorgeous, bums, chaotic, toxic, sweethearts; an array of the best to worst sort of men a woman can encounter.
We’ve ranked some of the love interests on the show from worst to best, and even if you disagree with most of this list, you’ll have to agree that the best and worst spots were duly earned.
10. Dro, A.K.A Open Marriage Bae
Of all the men who featured on Insecure in different capacities, Dro is the undeniable worst. Dro is that man that you know is bad for you, your friends know he’s bad for you, but you’re still hung up on him for some reason regardless. The “bad habit boyfriend”.
He’s a gaslighter, a man-child, and his height is his only redeeming quality.
Dro uses his open marriage as a crutch for his bad behaviour. He disregards Molly’s feelings and has the audacity to feel a way about her catching feelings; what did he expect?? He also hooked up with Molly in the bathroom while his wife was at the dinner table, and that is irredeemably trash behaviour, open marriage or otherwise.
He’s the type that’s sweet when he wants to be and affectionate only to draw you back in when you’re finally coming to your senses.
9. Lawrence, A.K.A Work in Progress Bae:
Lawrence had the best glow-up and character arc of any Insecure character aside from Issa. A sweet boy with caveats and a cute smile, but also really badly behaved when you examine it.
Issa and Lawrence had a 4+ year history, and in that time he became a lazy and complacent boyfriend. Laying on her couch all day, daydreaming, freeloading and then he had the guts to do nothing on her birthday? Bad of him. Like yes, we get it, he was down on his luck and depressed. But Issa deserved better.
He also suffers from “good man syndrome”. He tries not to be an asshole but needs to try harder. He needed to stop lauding himself for doing the bare minimum and being a quote-unquote good guy. Because a lot of the time, he really isn’t. Like with Condola. And Tasha who he led on. He’s also recently a baby daddy, is a drama and mess magnet, and he called Issa a “fucking ho” outside a dinner party in season two.
With Lawrence, Issa was in love with potential and was essentially on a build-a-man project; never a fun place to be. He did have abundant potential to be good, but a lot of the time, he wasn’t. And that’s disappointing.
8. Eddie, A.K.A Neighbour Bae:
Eddie, Issa’s neighbour was a very convenient lay. Always has weed and lives right downstairs? I see the vision. Sleeping with your neighbour though? Bad idea. He also wasn’t very upfront about the fact that he was seeing other people, but again, it was a filler thing, a fling at best.
Issa’s short-lived casual sex era was necessary for the phase she was in. Neighbour bae did what he was supposed to do, that arrangement was for one thing and one thing only.
7. Daniel, A.K.A Bae That Got Away:
Daniel is the ultimate f-ck nigga. Here for a good time, and not a long time. As Issa said, he was an “itch she needed to scratch.” Ouch.
Daniel is a fine man. Great teeth, great beard, good with children, great friend, and his body? Whew. He was Issa’s “what if?”, side bae who was also a friend material.
His bad behaviour (like sleeping with someone else while Issa was in the apartment, showing up to her work thing unannounced and nutting in her eye) aside, Issa and Daniel had a great connection. He truly saw Issa’s potential and believed in her. He was there for her at her lowest, and their reconnection was instrumental in her finding herself again post-Lawrence.
Issa felt unappreciated and taken for granted in her relationship with Lawrence, and Daniel provided a spark that was missing in her life. He was selfish though, and wanted her only on his terms.
He was good at communication and was open and honest (compared to some men on this list). He was definitely not “the one”, but he was a dependable friend and a much-needed rebound.
6. Chris, A.K.A Faux Bae:
Compared to Molly’s history and roster, Chris seemed like a refreshing change. Smooth talker, great at parties, Jidenna.
Truly, she jumped the gun on some things, but he did not have to be so mean about it omg. Showing up to her co-worker’s engagement party and introducing himself as her boyfriend when he fully intended to dump her afterwards? Mean, plain and simple. “I thought you needed a win” is such an evil thing to say. I’d be inconsolable. But at least he was honest, and Molly really needed to chill.
5. Nathan, A.K.A Ghost Bae:
Dreamy eyes, intense, sexy voice, and will throw a punch for Issa. He seemed like the perfect man, but then he ghosted for a whole month, an unforgivable offence. And we were rooting for him too.
The show addresses Nathan’s mental health struggles; his depression and bipolar diagnosis to explain his sudden absence. But it still didn’t make it okay for him to disappear for a month after Issa was so vulnerable. Besides, you don’t have sex with someone on a ferris wheel at Coachella and then just ghost. I can’t even imagine how Issa felt at his disappearance, even though we (obviously) saw it on the show. And then to show up with flowers unannounced on her birthday? No, thank you.
Nathan is a sweetheart, and we definitely understand what he was going through and sympathise with him, but vulnerability after the fact was just not enough.
4. Andrew, A.KA Boyfriend Material Bae:
Andrew was the sweetest man Molly ever dated, she fumbled so badly. He was dedicated, devoted, willing to be vulnerable and honest, called Molly out on her (abundant) bullshit and was an all-around decent guy.
He could be guarded, but he was willing to try for Molly, even when it was uncomfortable. He was a good match for her because he did not let her push him around and highlighted the things she needed to work on for herself and her romantic relationships. It’s sad that he gave up in the end, but it’s understandable. Molly was pretty chaotic.
3. Calvin, A.K.A TSA Bae:
Calvin was that person that you sleep with just because, but he was a gem. He showed up when Issa needed him and helped her out by doing security for her block party fundraiser.
He was funny, available, gave her confiscated TSA items, post-sex weed and Hennessy. We stan a supportive king. He’s a good man Savannah.
2. Jared, A.K.A Bisexual Bae:
Jared deserved better. With his puppy dog eyes, openness, and honesty, we thought he could be it for Molly, but apparently not, because Molly just had to be homophobic on top of all her other questionable character traits.
He was a gorgeous man, in touch with his emotions, confident and self-assured — but Molly is Molly, and there was always something with Molly.
1. Derek, A.K.A Tiffany’s Bae:
Derek was a good friend and a great husband, probably the best man on the show. He called Lawrence out post-breakup with Issa and made him see the role he had to play in it. He evolves and grows with fatherhood, and he’s nothing short of sweet to his wife. Bare minimum maybe, but look at this list and tell me he’s not the best of them.