Here's Where We Think the Incredibly Messy Relationships on 'Insecure' Are Headed

The characters of 'Insecure' are all over the place romantically. We have some predictions about how things will end up for them this season.

issa lawrence insecure
HBO

Image via HBO

issa lawrence insecure

Warning: Spoilers for seasons 1 and 2 of Insecure are all up and through this article. 

HBO's Insecure has sparked many heated debates here at the Complex office—and probably at your workplace/favorite bar/Twitter feed too. Conversations about the show largely center around the characters and how they're out here getting it how they live (shouts to the Hot Boys). But mostly, fans of the show come together to collectively pull our hair out over the many ways they're fucking up. The brilliance of Insecure is the relatability: we're so invested in these people because we see ourselves in them. We don't want them to do anything we wouldn't do—but we can't front like we haven't done our fair share of dirt.

Last Sunday's episode ended with Molly giving into the married Dro's advances, and it set off an avalanche of speculation: is Dro really in an open marriage, or did Molly just do some foul shit? That got us wondering about the other characters, too: is Issa honestly about that Hoe Phase life? Is Lawrence gonna try to win Issa back, or go crawling back to Tasha? Is Daniel catching feelings?

In an attempt to answer these burning questions, we've gathered Complex's pop culture critics and fans of the show to predict where we think our favorite characters are headed this season on the romantic tip. Read up.

Issa

Issa is really trying to be on her single-and-ready-to-mingle vibe, but she ain't about that life—at all. She's a wifey type through and through, so I do don't see her "ho-tation" phase lasting that long. If she doesn't somehow get back with Lawrence, which would be too safe of a play for the writers, I see her eventually settling down with Daniel or the Latin lover from last week. But knowing Issa's goofy ass, she'll probably fumble both options and keep making dumb decisions like Neighbor Bae. In my heart of hearts, Issa and Lawrence will eventually wind up back together—but that'll get dragged out until next season, at the earliest. —Anslem Rocque

Issa is lame AF for this Daniel thing. It was nice of him to rescue her from loneliness/awkwardness at the Kiss-n-Grind party, but that was NOT a sign for her to pursue anything with him—especially because she is not cut out for "casual sex." When Daniel shows her what the game really is, she's going to get her feelings hurt. My only advice is if Issa's going to have a "ho-tation," she needs to invest in some cuter panties and ditch those parachute bloomers we see every week. —Dria Roland

I don't care how much she wants it to be a thing, Issa's not emotionally ready for a "ho-tation." She wants to be free after feeling bogged down by sleepy Lawrence for a while, but truthfully she just wants to fill that void that he left. Issa appears to be more relationship-orientated and is probably better with Lawrence than without, but with neither of them trying to really work through their relationship problems and just acting out of their feels, it's going to be a long road of fuckery before they finally hash their problems out. —Khal

Issa's doing the absolute most in her attempt to move past Lawrence, and she's not fooling anybody. Her conversations about her "ho-tation" feel incredibly forced. I literally cringed when she said that. She's been doing a pretty decent job of masking her true emotions this season, unless she really is just over Lawrence and doesn't want to commit to anything serious moving forward. And if that's how she really feels, she needs to leave Daniel's sweet ass alone, and keep the casual sex to Neighbor Bae and other randos. Daniel doesn't wanna do anything but love her up and hold her down, even after Issa called him "an itch" she "needed to scratch." He must really feel something... damn. Issa, if you're listening: LEAVE DANIEL ALONE. —Kiana Fitzgerald

Molly

Molly... hooboy. Let's talk. Baby girl is going through it. She gave in and gave it up to the very ​married Dro, who claims he and his wife are in an open marriage. Only thing is, we haven't seen or heard from said wife in quite a few episodes. How convenient for Dro, to be able to sleep with someone he's probably had his eye on for years, guilt-free, right as his wife is out of the picture. My gut is telling me that this marriage is not open. And if it is, I have a feeling it wouldn't be open to a long-time friend like Molly. But let's say it is: where does Molly go from here? Was this a one-time thing? Or is she gonna become a regular partner in this open relationship? I'm gettin' stressed just thinking about it. —Kiana Fitzgerald

Poor Molly. I knew she'd fall into Dro's clutches at some point. And while my heart tells me he isn't lying about his, ahem, arrangement with his wife, my head is telling me that he's lying his ass off, and just wanted to finally sleep with Molly. Molly's already been hella self-destructive over a season and a half, and wasn't in the right place as season two began, so a broken heart could send her into a whirlwind that no one—not even Sterling K. Brown—can fix. —Khal

Damnit, Molly! Sterling K. Brown (Lionel) did nothing to deserve this. He's successful, handsome, kind, clear about his interest—all the things we thought Molly would want... and yet. Here's where this is going: Molly is going to end up with the friendly, funny coworker in Chicago (played by comedian Lil Rel). Is he the eye candy we've seen her drawn to in the past? Nope. But I think Molly is inching toward the realization that character and compatibility are most important. She'll find both in him. —Dria Roland

After straightening out her personal life, Molly done fell back into old tricks and into bed with a married Dro. It still remains to be seen if his unconfirmed "open marriage" is a real thing, because his constantly MIA wife is never anywhere to be found (we ain't seen her since the ice cream shop). In the aftermath of this tryst and her father's own infidelities, Molly is going to have a lot of emotions to unpack. But I think the biggest plot twist for her would be to end up pregnant by Dro. We never see condoms on this show and being knocked up by a married man would not only be a realistic wakeup call, but the eventual decision to keep the baby or not would make for some true character reflection. —Anslem Rocque

Lawrence

It's only a matter of time before Lawrence has sex with one or both of those female coworkers he's always with. You'd think he'd learn his lesson after the grocery hoes, but he's absolutely going to shit where he sleeps. This won't turn out well for him. I'm trying to give him the benefit of the doubt because he's youngish, has been in a relationship for five years, and is flailing a bit due to some genuine naivete. I do think he will realize the single life is not for him—perhaps he's seen that already, if him sitting outside his old apartment was any indication. But I gotta say it: I don't think he and Issa were cute together. As long as Tasha doesn't pop back up, I'm good with wherever this man ends up. —Dria Roland

Fuck boy No. 1, reporting for duty. I honestly haven't seen it for Lawrence since I saw him laying on that couch in season 1, feeling sorry for himself. Issa held him down for years, and he ended up taking too long to make something of himself, pushing her away in the process. Now, I'm not saying Issa isn't to blame for cheating—no question, she is. But ever since the breakup, Lawrence has been on a losing streak with women. He messed Tasha's life all up, for no reason other than the fact that he's selfish; and he got turned out by a couple of weirdos who picked him up at a damn grocery store. Now he's low-key stalking Issa via Kelli's social media? Come on, bruh. You got a solid job and a nice apartment, that's great. You glo'd up aesthetically, that's fabulous. But you still gotta get your shit together. —Kiana Fitzgerald

Hurt people hurt people. While Lawrence was spending X amount of time laid up on Issa's couch feeling sorry for himself, she stood by him... until she slipped up. And while she fucked up, Lawrence has been a proper fuccboi to Tasha, to Issa, and ultimately, to himself. He wants Issa back, but he's too hurt to admit it, or get out of this "I got money let me cop a Jag to feel better" phase. He's not worked on himself, and will more than likely get sweaty with one of the women at work (probably the blonde one). —Khal

After sowing his wild oats for a few months, Lawrence is back to pining over Issa. I feel like it's more of a matter of all his other options not panning out (i.e. Tasha, the Sunken Place girls from the grocery store, etc.) and he's trying to get that old thing back. But it might be too little too late—for now. He's probably going to continue his social media stalking and even run into Issa with Daniel or one of her other "ho-tation" tributes—much like she planned at the failed house party—and get even more in his feelings. Lawrence might pull a Molly and find comfort in the open arms of one of his co-workers, but office romances are a recipe for disaster and more drama we'll be tuned in for. —Anslem Rocque

Bonus predictions

Issa and Lawrence

Both Issa and Lawrence need to accept that they are BAD at being slutty. I mean look at them: Issa got in a car accident because of a dick pic (which, fair enough) and Lawrence was in a Get Out threesome. I just don't think they need to get back together in order to do this; they can figure this out on their own without backsliding. But I do think that this will happen in very different ways. I think after getting this realization that DUH, Daniel has feels for her, Issa is going to rethink her whole roster situation. And I also hope that Issa pursues Nico—the hot comic book-loving guy that she had that great date with—because he's hot and also seems like a grownup and that would be good for her. As for Lawrence, he is just making bad decision after bad decision after being such a douche to Tasha (#teamtasha) and the aforementioned Get Out threesome. I don't think it's gonna stop there, either. I bet that he ends up sleeping with one of those coworkers that we met at the very drunken tech mixer they all went to; it's just going to spiral from there. And making more of those bad choices is what's gonna lead Lawrence to his come-to-Jesus moment. —Kerensa Cadenas

Tasha

She might be over her crush on Lawrence and his fuccboi behavior, but we ain't seen the last of Tasha. She's going to pop back up at some point and throw salt in Lawrence's wound when she's glo'd up with the next dude—hopefully, someone who appreciates her stable income, home-cooked meals, and bedroom magic. She might have been the rebound chick, but I see her bouncing back first and better than ya boy L. —Anslem Rocque

Chad

Never mind Dro and Candice; where the hell is Chad's fiancée? This man flirts with everything walking, but was trying to tell Lawrence last season about proposing. Where is his woman? Does she know she's engaged to a dog? Will they make it down the aisle? Will he hip his young friend Lawrence to the game? —Dria Roland

Daniel

Daniel, Daniel, Daniel. There are so many guys like Daniel who don't want to admit it. For whatever reason, they put up a front like they are really collected and chill with riding solo dolo, to the point where they put off even trying to connect with someone who's obviously feeling them. That seems to be Daniel's issue, as he totally missed the boat with Issa back in the day. Her relationship status in season 1 ruined any chance of them actually becoming a thing, and now, when Issa's playing the field, he's getting attached. Dude should truly run, but most people take the easy way out when it comes to matters of the heart. He'd rather hide his real feelings and enjoy his time with Issa than admit that he's digging her and wants to see where it can go. He's going to get hurt, and it's not going to end well—especially because he already lied. Good luck, but you fucked up, Daniel. —Khal

Kelli

Okay, I know I'm not the only wondering about Kelli's romantic fate. She's hands down the most carefree of the friend group, and doesn't seem to be trying to settle down anytime soon. That being said, I feel like Sweetie—you know, the dude who gave her finger service under the table at a diner—might be a potential long-time suitor. He seems like he has just enough fire in him to keep her excited. Pshh, who am I fooling? Kelli can't be contained. —Kiana Fitzgerald

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