"You all over the place."—Issa Dee's latest significant other Nathan sums up Insecure's beloved lead character pretty accurately in a recent episode of season 5. HBO's hit comedy series, created by and starring Issa Rae, follows the friendship, love lives, personal lows and highs, and professional endeavours of two thiry-something Black women. As they navigate the tricky terrain of living and working in Los Angeles, best friends Issa (Rae) and Molly (Yvonne Orji) face the challenges of being Black women who, against all odds (and stereotypes), dare to push forward and be the best version of themselves.

Rae initially garnered a following with her successful webseries Awkward Black Girl, so longtime fnas of the writer/actor/showrunner had high expectations when Insecure got picked by HBO in 2016. Of course, Issa being Issa, Insecure became a smash hit in no time, with episodes artfully exploring the complexities of Black millennial life. "A lot of people have asked me over the years how much I identify with the character, and in those first couple of seasons, I felt like Issa was the younger version of me," said Rae to Vogue about her show's protagonist. "By the time I had done the show, I knew who I was, and I was confident in the path that I was on, and we were creating this character who’s not yet. So much of your 30s is about establishing yourself and understanding what your purpose is and finding your passion. The short answer is: It just mirrors my own journey."

Insecure has effectively woven together multiple storylines over the course of its run, but perhaps the most fascinating one remains to be the ever-evolving love life of its protagonist. From Insecure's debut season to now, Issa's pursuit of love and sex have led her to a bevy of good-looking men. As the fifth and final season comes to a close, we look back at—and rank—all of the supporting players that Issa has dated over the years.

Related: Issa Rae is Spider-Woman in Spider-Man: Into the Spider-Verse 2

6 Felix

Hunter_Felix_Insecure_IMDb
Via HBO

Sometimes, looks don't match personality. Such was the case with Felix (played by Broderick Hunter), a guy who matched with Issa on Tinder at the beginning of season 2. Despite his good looks, Felix was hypercritical of everything and everyone—including Issa. Fans of Insecure's hero can agree that Felix didn’t deserve her.

Related: Little Review: Marsai Martin Shines in Silly Update of Big

5 Eddie

Thomas_III_Eddie_Insecure_Boombox-1
Via HBO

He'll smoke you out, watch Gossip Girl with you and know how to take a hint. However, he might not wait around, and sometimes he isn't exactly direct. Meet Eddie (played by Leon Thomas III), who had a bumpy start with Issa in the bedroom, but they quickly found their groove. Sleeping with your neighbor can be convenient — but also complicated. Issa found herself in bed with Eddie after finessing an invite in the name of borrowing a phone charger. Things with Eddie didn't last too long, which is probably for the best. Felix played his role.

4 Calvin

Conquest_Calvin_Insecure_HBO_IMDb
Via HBO

"Brrrat!" Imagine dating someone whose catchphrase is that machine-gun sound effect music artists occasionally include in their songs. We were first introduced to Calvin (Reggie Conquest) in the season 4 premiere, and he wasn't what most Insecure fans were expecting. But Issa doesn't really a have a type, it seems. — good sex seems to trump all other attributes. And Calvin was certainly good for that.

Calvin — AKA "TSA Bae" — was also supportive. At one of Issa's mixers, for example, Calvin puts his skill set as a TSA employee to work by providing free security. He even makes sure to hype up the party to all the guests.

3 Nate

Rae_Sampson_Insecure_HBO
Via HBO

Along with dreamy eyes and a sexy voice, Nathan (or just "Nate") is even willing to throw a punch for Issa — as we found out in season 5's recent episode. But Nathan will ghost at a moment's notice — before even alerting those close to him that he suffers from bipolar disorder. It was heartbreaking that his AWOL nature first affected Issa after their intimate moment on the Coachella ferris wheel. Nathan finds himself in middle of our ranking, and he can thank his character for the mediocre scoring. Ghosting is arguably a sign of emotional immaturity. He seemingly had good reason for needing to take a step back — but could have at least let Issa know first.

Related: Nathan Fielder Is Creating a New Comedy Series at HBO Called The Rehearsal

2 Lawrence

Ellis_Rae_Insecure_IMDb
Via HBO

"With the character of Lawrence, you see that he really is trying," said Rae to Vox about her on-again, off-again boyfriend in the show. "He’s taking a similar journey to Issa, of getting his confidence back. That’s one of the storylines I really like on this show: this simultaneous journey they’re both taking on to be better."

Lawrence seems to have the best "glow-up" of all the characters so far. And him and Issa still have great chemistry together. But this is Insecure we're discussing, so it's no surprise that he comes with caveats. It works in Lawrence's favor that has at least four years with Issa under his belt. They like a lot of the same music and movies, including The Last Dragon, and they have similar goals.

However, let's not forget that Lawrence previously fed off Issa for years. Remember when he wouldn't leave their apartment, or change out of sweatpants? He also falls victim to jealousy and vindictiveness, as exemplified by his revenge-sex with Tasha in the season 1 finale and his calling Issa a "f***ing ho" outside a dinner party in season 2. Plus, there's the newly added baggage that was first revealed in the season 4 finale: He had a baby with Condola,

It was only after Issa cheated on him with Daniel (Y'lan Noel, discussed below) that Lawrence was able to grow up. He left Issa and their shared apartment (and his iconic Best Buy uniform), finally got a haircut and got a great job working at a tech startup. But he's also prone to jumping the gun and acting selfishly, as displayed by his confrontation with Nate in the latest episode this season.

1 Daniel

Rae_Noel_Insecure_IMDb
Via HBO

He's easy on the eyes, and he truly believes in Issa. It's too bad Daniel (Noel) started out as "the other man," and that he suffers from excessive pride and insecurity. It's also unfortunate that a certain oral-sex fiasco led Issa to dump Daniel, and that she felt the need to call him an "itch she needed to scratch."

It's clear that Issa's exes are, for the most part, visually stimulating—but what pushes Daniel over the edge is the strength of his connection with Issa. He really knows her and accepts Issa for exactly who she is. The shady origins of their relationship may have doomed Issa and Daniel's connection from the jump. They couldn't quite get into the swing of things once they were both ready to make it work. For now, as we await the events of Insecure's finale, we can hold on to memories of Issa's epic first kiss with Daniel in his studio.