In 2016, Issa Rae's Insecure hit HBO, and longtime fans of the writer and showrunner had high expectations following the success of her web series Awkward Black Girl. Issa being Issa, Insecure became a smash hit in no time, with episodes artfully exploring the complexities of Black millennial life.
One of most fascinating storylines in the HBO original series is the ever-evolving love life of its protagonist, Issa. From Insecure's debut season to now, Issa's pursuit of love and sex (and we're talking really, really good sex) have led her to a bevy of impossibly good-looking men. I know we said that Insecure is relatable content, but I don't know — most of my exes didn't look that good.
With the fourth season of Insecure officially underway, we have to look into our plucky heroine's past to predict what lies ahead in her future. Issa's probably going to meet someone new and very fine this season, but but given her dating history, her new man will either be the best she's ever had or the worst. And that's saying something.
If there is a new beau in the picture, he's going to have a lot to prove — where will he will he stack up against Issa's exes? Ahead, a comprehensive ranking of the men our heroine has been romantically (and otherwise) entangled with since the very beginning of Insecure.