I Ranked All Of Issa And Molly's "Insecure" Lovers From Most To Least Likely To Gaslight You

·7 min read

I’m still crushed that Insecure is ending. The hit HBO series granted us an iconic cast of characters that made Los Angeles feel cool again.

HBO / Via giphy.com

And I know the backbone of the show is the relationship between besties Issa and Molly. But y’all.

It also blessed our screens with some fine ass males.

HBO / Via giphy.com

The final season drops this Sunday on HBO and I just know we're going to see most, if not all, of the boys Issa and Molly have ever "loved." I have thoughts on all of them.

So from 'nay' to 'bae,' here's my ranking of all the male flings from Insecure:

Warning: an abundance of spoilers and hot guys with problems ahead.


Sarunas J. Jackson as Dro and Molly in "Insecure"

Pros: Tall.

Cons: Everything else.

Dro is as mature as three toddlers on each other's shoulders wearing a trench coat to pass as an adult (and as tall as that too). It's cool that he's in an open marriage, but he constantly uses that as an excuse to not mind Molly's feelings. That makes me hate him more than I hate Molly.

I already didn't like Dro when I looked up how tall he was. But when he hooked up with Molly in the bathroom while his wife was back at the dinner table? Trash. And then he has the audacity to get mad at Molly for developing feelings! Like does he not know he's sleeping with? Ass.



(Top) Kendrick Sampson as Nathan brings flowers for Issa and is intercepted by Molly (Bottom) Nathan returns later that night to meet Issa outside her apartment

My opinion on Nathan is in the first syllable of his name: NAY.

Pros: Dreamy eyes. Sexy voice. Willing to throw a punch for Issa.

Cons: Will ghost at a moment's notice.

I appreciate that the show took care in addressing Nathan's depression and bipolar diagnosis to explain his sudden absence, but that doesn't make it okay to disappear for a month. You don't just have sex with someone on the ferris wheel at Coachella — while on ecstasy — and go AWOL after that. Even if it's about you, that's still hurtful. And then you wanna show up with flowers on her birthday? Nah, man.

I love that Nathan is trying to be better, but he can leave Issa out of that journey.



(Top) Jidenna as Chris in "Insecure" gives Molly a hard time at a party (Bottom) Chris and Molly in bed post-sex

Oh, this piece of work from The League dating app. I had to look up his character name because I truly thought it was Jidenna.

Pros: Smooth talker. Great plus-one. Classic man.

Cons: Thinks low of Molly. Too real.

While I do think that Molly needed a nudge towards not moving so fast in a relationship, this dude was so cold-blooded in delivering the truth that it felt like a shove to the ground. I mean, showing up to her co-worker's engagement party and introducing himself as her boyfriend when he fully intended to dump her afterwards? That was mean. "I thought you needed a win" is truly a line that will haunt me forever.

At least he was honest.



Jay Ellis as Lawrence in "Insecure" with Issa

Lawrence undeniably has the best glow-up of all the characters so far. And him and Issa still have great chemistry together. But honestly? He comes with caveats.

Pros: History of 4+ years with Issa. They like a lot of the same music and movies, like The Last Dragon. New goals. Same ole' goofy smile.

Cons: Fed off Issa for years. Gets jealous easily. Vindictive. Thrives on being a "nice guy." Moving to San Francisco. About to be a baby daddy.

I don't think I'll ever fully forgive Lawrence for slighting Issa and revenge-banging Tasha in the season one finale. Or for calling Issa a "fucking ho" outside a dinner party in season two. And just when things are finally looking up for him and Issa, he's really about to have a child with Condola-virus?! Uh-uh. The devil wears drama and Lawrence is dressed head-to-toe in it. Sorry #LawrenceHive.


6.Eddie the Neighbor

Leon Thomas as Eddie takes off his shirt after Issa's removed her top in "Insecure"

If I found out I lived above Andre from Victorious, I would also pretend he left his iPhone charger at my place.

Pros: Knows how to take a hint. Watches Gossip Girl. Will smoke you out.

Cons: Skipped season five of Gossip Girl. Won't wait around. Not direct.

Him and Issa had a bumpy start in the bedroom, but they quickly found their groove. There's something really convenient about sleeping with your neighbor, albeit complicated. It's cool that he helped Issa get back into her "ho-tation," I just wish he could've been a part of it longer. He moved on pretty quickly, which sucked for Issa and her casual sex era, but honestly, good for him. It's just lame that he tried to cover it.



Lil Rey Howery as Quentin jokes with Molly and later hooks up with her on the couch in his office in "Insecure"

Molly's old co-worker from Chicago who has "the body of a pastor."

Pros: Educated. Smart sense of humor. Same career as Molly. Patient. Listens. Gives great advice.

Cons: Lives in Chicago.

I feel like Molly and him had great rapport. Quentin cared about Molly and encouraged her to move forward in her career and join a new firm that actually valued her. He was so warm to her that she pulled him out of the friend zone and grinded on him on an office couch. They really could have learned a lot from each other. Unfortunately, she was too hung up on three boys in a trench coat — oops, I mean Dro.



Alexander Hodge as Andrew comforts Molly as she rests her head on his shoulder in "Insecure"

Pros: Gives 100% to his girl. Talks things out. Challenges Molly. Happy to help his partner's friends.

Cons: Bottles up his frustration. Guarded at times.

What I like most about Andrew is his commitment to being honest, even when it's uncomfortable. He didn't let Molly push him around in the beginning of the relationship, which is why he was so good for her. That's why it was sad to see him eventually fold towards the end of their relationship, as if he was done fighting. Then again, Molly does have a lot going on.

Merie W. Wallace / Via HBO

3.Calvin aka "TSA Bae"

Reggie Conquest as Calvin aka TSA Bae in "Insecure" provides Issa with free security, marijuana, and alcohol

Pros: Funny. Supportive. Offers free security. Shares what he confiscates.

Cons: None.

Our first impression of Calvin is him trying to find a sex position that pleases Issa and he doesn't stop until he lands it. I love a man that likes to solve puzzles. He also gifts her weed and Hennessy post-coital. Um, hell yes. He even works security for Issa's block party fundraiser and I have a feeling he's the one that offered to do it. He supported Issa and shared his treasures with her. Good man.



(Top) Y'lan Noel as Daniel appears shirtless in Issa's imagination in "Insecure" (Bottom) Daniel and Issa are all smiles at a late night diner

Pros: Stunning. Great teeth. Good with kids. Best beard on the show. Believes in Issa.

Cons: Started out as the other man. Too proud. Insecure.

Chiseled chest aside, Daniel is up here for me because I felt like he truly saw Issa. Their reconnection is what set the whole series in motion. He hyped Issa up and believed in her and her music. I get that it may have felt like he only kept Issa around when it was convenient, but let's not forget how Issa told him he was an "itch she needed to scratch." That even stung me.

I still can't believe Issa dumped Daniel for nutting in her eye. This episode gaslit the hell out of me because honestly? That sounds like my kind of night. Then again, I'm not a woman. Or Issa.



Langston Kerman as Jared eats Cookie Crisp cereal before screwing Molly against the wall in "Insecure"

Pros: Loyal. Honest job. Open to new experiences. Not afraid of independent women. Will share his cereal. Can give you a ride.

Cons: Nothing.

When Jared slid over his box of Cookie Crisp over to Molly, I fell in love a little bit. He was a sweet and dominant dude. A real catch. So Molly calling it quits with him just because he slept with one man in the past was beyond infuriating. She missed out on a really good guy. I wish he would return...

At least I'll think about him every time I run some errands.


Who do you want Issa and Molly to end up with, if anyone at all? What guys do you wish would return for the final season? Be thirsty with me in the comments.