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“Insecure” Men Ranked From Worst To Best

Instagram @kendrick38

Since 2016, Insecure has been a hit for HBO. Following the Success of Issa’s “Awkward Black Girl.” There were high hopes that “Insecure” will also be a hit. The show is great for many reasons but the best is Issa’s evolving love life. She’s her own protagonist and antagonist. Although her best friend Molly is also always a protagonist, I digress. This evolving love life leads to a hefty list of men as well. With four seasons, and new and old men in each. We will get to dive in and see the worst and best. Since she has a new beau every season this will be fairly easy.

The Worst

10. Dro

Instagram @ronejae

The WORST character to ever walk the show. (After Molly of course.) This man was horrible. He teased Molly with the idea of a real relationship despite him being a married man. He is the definition of gaslighting. Leading her on was immature. His marriage was immature. He just sucked.


9. Chad

"Insecure" Chad

Courtesy HBO

Lawerence’s best friend. I find him calming to watch because he’s the normal one. He doesn’t pretend to be anyone else. He always tells his friends like it is. Everyone needs a Chad.


8. Eddie aka “The Neighbor Bae”


After Lawerence first moved out of their apartment, Issa met Eddie. She was struggling to get back into the game and just when Eddie came along she felt like herself again. She pretended to need a phone charger and made her move, then got in the groove. Luckily, that little fling didn’t last long. Eddie wasn’t a character we needed.

The Okay

7. Nathan aka “Ghost Bae”

Instagram @kendrick38

Ugh, beautiful Nathan. It was love at first sight for all of us. Nathan was just what Issa needed at that time. She was still figuring out things and trying to get better with herself. However, after weeks of perfectness, he ghosted her! It should’ve been easy to catch on that something was wrong. Especially since he was very mysterious from the start. But, depression is no joke. Sometimes you have to go away. He still could’ve talked to Issa about it though. It isn’t a reach to say that he helped her become a little Insecure.


6. Daniel aka “The Bae”

"Insecure" Daniel

Instagram @Insecurehbo

Now all of the men were toxic in their own way. That is true. But Daniel, his toxic trait was how well he knew Issa. He knew Issa like the back of his hand and accepted her flaws and all. They did start off very shady. That was also probably why their relationship didn’t go well. She called him an itch and he slept with people in the next room. They may never end up together and that’s okay.


5. Lawerence aka “Unmotivated Bae”

"Insecure" Law

Instagram @Insecurehbo

My sweet Lawerence. Now let’s be clear. He isn’t the worst guy Issa has dated. In fact, he’s one of the best that’s why he’s in this section. At the time though, he was the least motivated and the most broke. Let us keep in mind he was broke because he wanted to be. Not because he couldn’t get a job. He was not carrying his weight in their relationship. Not emotionally, physically, mentally, or financially. It was honestly embarrassing. It took her cheating with Daniel for him to get it together. Which, when he did it was a phenomenal job. He became bae again. In season 4 we did have hope for them but like always, something or someone I should say is always in the way.

The Better

4. Calvin aka “TSA Bae”

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📸 @mikebryknyc with the snaps! 🕺🏿

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So our first meeting with Calvin was.. different to say the least. He definitely wasn’t what we were expecting but we should know by now Issa doesn’t have a type. She really was using him for just sex and he seemed perfect for the job. He was supportive of her events. None of her other male friends has done that before. So he’s a good one.


3. Derek

Courtesy HBO

He was an honest friend to Lawerence. He also matured right before our eyes. His traditions expanded as the season progressed. This easily made him a new fan favorite.


The Insecure Best

2. Andrew


Andrew is our top bae. He was always honest with Molly. Their interactions were mutual and he always remained strong in their relationship. Despite their rocky start, Andrew was perfect for Molly. However, Molly ruins everything so all good things come to an end.


1. Jered

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Fart… but make it fashion 📸 x @moreguinness

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He deserves the top spot for many reasons. Loyalty, confidence, and forgiving. Jered gave Molly a chance after chance. Molly let her insecurities influence their relationship. He didn’t graduate from college. He works at Enterprise. So what? Molly was just nitpicking. Luckily, Jered saw his worth and realized Molly didn’t deserve him.

Insecure had a lot more men and a lot more drama. Hopefully, in season 5 Issa finds her true happy ending.


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