Watching Issa struggle to find love throughout the last five seasons has been entertaining to say the least. Issa’s pursuit of love and sex after getting out if an long-term relationship has led this pretty yet awkward to a bevy of hot guys. Now that we’re halfway through the final season of Insecure on HBO and Issa has found herself in yet another relationship with another seemingly great guy. It’s on my right that we take some to reflect on our heroine’s relationships by ranking her exes from worst to best.
1. Felix
Do you remember when Issa met Felix (Boderick Hunter) after matching with him on Tinder during her self-proclaimed his phase? If there was a trash can button in the television screen we would have definitely dumped Felix in it. Sure, he was gorgeous but his personality was atrocious. Felix criticized everything and everyone including Issa. He didn’t deserve her at all.
2. Eddie
Eddie (Leon Thomas III) was Issa first attempt at moving on after Lawrence officially moved out their apartment. Clearly, Issa was thinking with the amygdala side of her brain which is responsible for arousal and sexual desire. Feeling incredibly lonely and horny in her new single hood, Issa finessed her way over to Eddie’s apartment by asking to borrow a charger since they were neighbors. Yes, I said, neighbors. Clearly. I saw didn’t get the memo that explicitly states that neighbors are off-limits.
Fortunately, Issa and Eddie’s session was nothing more and nothing less and the sex wasn’t Exactly spectacular. Whew, close call!
3. Nathan
Nathan (Kendrick Sampson) was a Greek God, a total hunk, and every other adjective you would use to describe a handsome man. His southern twang and ocean blue eyes could turn any woman into a puddle. Unfortunately, Nathan and Issa’s relationship or lack of thereof came to an abrupt end when he ghosted her which was downright cruel because they had already begun connecting on a really deep level.
Nathan’s sudden departure had Issa breaking into his apartment to get answers. Even though Nathan was handsome he brought a measure of toxicity to Issa’s life that she definitely didn’t need. Ghosting is a sign of emotional immaturity and that is a major red flag. However, we do find out in the Season 3 finale that Nathan was dealing with some mental health issues. But c’mon he could have at least let Issa know that he needed to take a step back.
4. Calvin
Calvin was a TSA agent. Calvin and Issa met in Season 4. Calvin isn’t exactly Issa’s type but he’s good in bed and that’s enough for her at the moment. Calvin was actually sweet and probably more supportive then all of the men we’ve seen Issa with over the years. At Issa’s block party he worked security for free and he even hyped up the block party to get more people to come.
5. Ben
Can we take a moment to admire the awesomeness that is Luke James? Like James played Ben on Season 2. I saw and Ben met on Tinder. Ben had the potential to be a good boyfriend but he caught Issa at a really vulnerable time. She wasn’t all the way over Lawrence and her head wasn’t really in the game.
6. Lawrence
Lawrence was the brokest guy that Issa ever dated but at one point they were deeply in love. While Issa is often painted as the villain in her and Lawrence’s demise, the truth is that they had settled into a toxic rhythm where Lawrence failed to show up financially and emotionally. When Issa cheated on Lawrence with Daniel he broke up with her and had one of the biggest glow ups in television history. He got a great paying job at a tech company and got his own place. Issa and Lawrence will always have a special bond but they have both moved and getting back together would be beating a dead horse.
7. Daniel
Issa risked it all for Daniel. Daniel is undeniably handsome and he just may be “the one that got away”. Out of all the men in Issa’s life, Daniel really knew Issa and accepted her for who she was because they were really good friends before anything. Daniel was even there for Issa and let her sleep in his couch when she got evicted after she was cruel to him after their hookup and told him that “he was just a itch that she had to scratch.” Daniel was a catch and as much as we wanted it to work between him and Issa, the shady way their intimacy started ruined the possibility of a good relationship.
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