The newly dropped trailer for the fifth and final season of Insecure just dropped and we are feeling the glowed up and growed up teas felt all throughout the two-minute preview of what's to come. Since its debut in 2016, we have laughed, we have cried, we went back and forth about being Team Lawrence, we've gotten annoyed AF by the Molly in our lives, but most of all, we have collectively felt seen in a visual representation of what it means to be a Black woman navigating through life and its many uncertainties. Season 5 of Insecure, which is set to premiere October 24 on HBO Max, is sure to be the homegoing we didn't know we needed.
But in the meantime in between time, let's get caught up on everything you missed in the trailer of what's to come this season on Insecure.
Are Molly and Andrew still together?
HBO/YouTube
At the end of season four, we were left on a cliffhanger of how the conversation between Molly (Yvonne Orji) and Andrew ended. Though their witty banter was cute, that got old real quick as the two had to make adjustments in their lives to balance love and work, but also to manage relationship pains that naturally came about as you are embarking on a new relationship with someone. While Andrew seemed willing to move, Molly seemed a bit stuck in her ways, a reality that also seemed to show its hand in her rocky friendship with Issa (more on that in a few).
From the looks of the trailer, Molly and Asian Bae are no longer a thing.
Molly is putting herself first.
HBO/YouTube
You know what they say, when a woman cuts her hair, she changes her life. From what we saw in the trailer, Molly the character is borrowing some real-life self-love juice from the actress that plays her, Yvonne Orji. Yvonne did a big chop and rocks her natural hair quite often off the screen. Molly ditching the wigs and weaves (some of the time) to embrace her natural hair in the series as well, which we love to see!
She also mentioned to her mother that she is not looking to date, she is focusing on her damn self. Since the start of the series, Molly has always placed a huge emphasis on "having it all" and that included having a time clock on having a man. To see her take a step back to prioritize herself is a huge step. Yasss sis!
Issa and Molly are working on their friendship.
HBO/YouTube
Something that fans loved and were divided on was the friendship breakup Issa Dee and Molly were going through in much of season four's overarching storyline. But, it was really real. As the two friends' lives grew and their priorities shifted, it was like they forgot to have important conversations and then their friendship suffered as a result. In the trailer, Molly can be seen asking Kelli (Natasha Rothwell) how she and Tiffany navigated a similar season in their lives. It's a testament to the fact that sometimes friends can outgrow each other, yes, but if there is effort, it might be possible to grow together.
Tiffany seems back to normal again.
HBO/YouTube
After a bout of baby blues that was explored during an episode last season, Tiffany (Amanda Seales) seems to have bounced back to being her bad and bougie self. Based off her quips in the trailer at least. Last season, she was notably detached from her little one after giving birth, so much so Kelli had to step in and fill in in areas Tiffany couldn't be a part of due to her postpartum depression. She also seems to be settling into her role as a mother.
Kofi Siriboe is in the building.
HBO/YouTube
Kofi Siriboe has been pulling double-duty starring in Queen Sugarand hit Netflix movies like Really Love. This year, he starred in Doja Cat's "Streets" music video and has been making movies as a business owner with his brand, We're Not Kids Anymore. And now sir is about to be guest-starring in the final season of Insecure? Issa Rae, you are a visionary!
Issa is still insecure about her place in the world.
HBO/YouTube
Despite the professional glow-up of Issa's character walking away from the comfort zone of her job (We Got Y'all) to pursue the dream that set her soul on fire, sis is still battling life's many uncertainties. She leveled up by pulling off an incredible event last season and from the looks of it, that move has opened career doors. But as Issa said in the trailer, she's ready for her life to be in the place where she isn't so unsure about everything. Girl, aren't we all?
Some of the career doors that are opening for her are making her feel like she's playing a role versus walking a path where she's successful in reality. It's something that a lot of us are sure to find relatable, myself included, but what's beautiful is amid the self-doubt, there are pockets of joy as she acknowledges where she's come even if she still has a way to go.
What's up with Issa and Lawrence?
HBO/YouTube
Umm, we don't know for sure if Lawrence (Jay Ellis) and Issa are still a couple. But with that earth-shattering announcement he revealed in the season four finale, we can't imagine that their second chance at love survived it. But it's quite possible that the two are doing their best to work through it. Personally, we really see it for her and Nate (Kendrick Sampson). Just saying.
Only time and the season premiere will tell us definitively where she and Lawrence stand post-baby gate.
But also, whose baby is that?!?!
HBO/YouTube
Chile, we don't know. But we have our best guesses... Sips tea.
Watch the official trailer for 'Insecure' Season 5 below:
Featured image by HBO/YouTube
- Everything We Know About 'Insecure' Season 4 - xoNecole ... ›
- Insecure Season 5 Premiere Episode, Takeaways - xoNecole: Women's Interest, Love, Wellness, Beauty ›
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Her captivating command of the pole left many of us intrigued, perhaps even tempted, to explore pole dancing ourselves after witnessing the mesmerizing performances at Mercedes Sunday. But it wasn’t just her physical prowess that kept us hooked. Mercedes is a character of depth—empowering, complex, relatable, and deeply human.
These are qualities that Brandee embodies both on and off the screen.
(L-R) Marque Richardson and Brandee Evans on 'UnPrisoned' Season 2
Courtesy: Hulu
A Memphis native, Brandee is no stranger to dance. She boasts an impressive career as a choreographer, having worked with renowned artists like Katy Perry, Monica, Ke$ha, and Ledisi. But while it has been a significant part of her journey, Brandee has her sights set on more—expanding her acting career beyond dance-inclusive roles. This ambition nearly led her to pass on the opportunity to appear alongside Kerry Washington in Hulu’s UnPrisoned, where she plays Ava, Mal's (Marque Richardson) new girlfriend.
“When Kerry Washington slid into my DMs, I nearly said no,” Brandee revealed with a laugh. “She mentioned pole dancing, and I told myself and my team that once I was done with Mercedes, I wasn’t going to do that again.” Fortunately, Washington assured her that the role would be vastly different, leading to what Brandee described as an invaluable masterclass in comedy under the guidance of Washington herself.
“Kerry is a force of nature,” Brandee reflected. “She’s everything you’d hope she’d be—strong, compassionate, and incredibly talented. Working with her was like a masterclass in acting.” This opportunity was no mere stroke of luck; it was something Brandee had manifested years earlier. But make no mistake–she credits her faith and praying hands for her success. “I’m praying, you know what I mean? I’m asking God for what I want and working for it too,” she said.
"When Kerry Washington slid into my DMs, I nearly said no."
(L-R) Brandee Evans, Kerry Washington, and Marque Richardson on 'UnPrisoned' Season 2
Courtesy: Hulu
This role marked Brandee’s first foray into comedy, and while she was eager to embrace the challenge, she found herself in the hands of an incredible mentor. “Kerry was always so kind in her critiques,” Brandee noted. “She’s not a diva by any means. She knows exactly what she wants, but she’s gentle and encouraging in bringing it out of you. That’s something I’ve taken with me to other sets—I want to lead with the same kindness and openness that Kerry showed me. It’s a lesson I’ll carry for the rest of my life.”
Brandee speaks with profound respect and gratitude for her peers and fellow actresses as many have shown her genuine sisterhood and support in an industry often notorious for its competitiveness. “Danielle Brooks sent me a prayer the other day, and I was just so touched. Those are the moments that people don’t see,” she shared. “I call Sheryll Lee Ralph my fairy godmother, and Loretta Devine is like my auntie. Being able to pick up the phone and seek advice from these incredible women is a true blessing.”
And she pays it forward.
Brandee Evans
Courtesy: Hulu
But her commitment to supporting others extends far beyond her career. As an advocate for health and wellness, she empowers women to prioritize their well-being. “Azaria [Carter], who plays my daughter on P-Valley, mentioned wanting to start a weight loss journey and get more fit. I told her, ‘Well, let’s work out together,’” Brandee recounted. But her dedication to healthy living goes beyond physical fitness, encompassing a holistic approach to wellness. “When she came to my house and tried to microwave something in plastic, I said, ‘Let’s use glass instead. At 20, I wasn’t thinking about that, but let me share some tips now so you’re not battling fibroids in your 30s.’”
Because she was.
While filming the first season of P-Valley, Brandee faced enormous stress—not only as a caregiver for her mother, who was diagnosed with multiple sclerosis, but also due to the physical demands of the role. Yet the impact on her body was far greater than she expected. “I was literally on my cycle every day while playing a stripper, which is far from ideal,” Brandee revealed. It was Harriet D. Foy, who plays her mother, who urged her to get checked for fibroids.
"I was literally on my cycle every day while playing a stripper, which is far from ideal."
Brandee Evans graces the 2024 ESSENCE Black Women In Hollywood Awards Ceremony.
Arnold Turner/Getty Images for ESSENCE
The statistics are staggering—80% of Black women develop abnormal uterine growths by age 50, making them more likely to suffer from fibroids than any other racial group. But like many, Brandee was initially unaware of these growths and their debilitating effects, and the prospect of surgery was daunting. “I was scheduled to have a myomectomy on my birthday, but I thought about what it would mean for my career. How am I going to climb the pole? The healing process is similar to a C-section.” Determined to avoid surgery, she committed to healing herself naturally.
After a deep dive, she sought treatment at The Herb Shop of Vinings in Atlanta, which ultimately led to a remarkable recovery. “This man saves lives. His name is Jeff, and I call him my doctor.” Brandee shared. “I started detoxing my body with herbs and following his program. During my follow-up with the gynecologist, they said, ‘We don’t know what you’re doing, but your fibroids are shrinking.’”
Emerging on the other side of this journey not only fibroid-free but with a regulated cycle and a renewed outlook on life, Brandee is now focused on sharing her story and advocating for women’s health. “I know y’all want to hear about P-Valley, but I want to talk about regulating your period,” she said with a laugh.
Of course, she didn’t leave fans hanging when it came to what to expect in the upcoming season. “It is worth the wait. The world is about to go crazy. Oh, the world is about to lose it,” Brandee teased. “Y’all might be mad at us right now, but baby, it’s going to be worth it.”
All episodes of Season 2 of UnPrisoned are now streaming on Hulu.
Featured image courtesy of Hulu
You will see everything from Bored Panda’s “33 Older Adults Share Their Feelings On ‘The One Who Got Away’ Now That Time Has Passed” and BuzzFeed’s “’I Still Think Of Her Daily’: Older Adults Are Sharing If They Still Have Feelings For ‘The One Who Got Away’” to data which says that close to half of Americans have not only thought about an old crush or past love, they’ve also used the internet to look them up (uh-huh, y’all be careful out here: “Baby Bliss Is Ruined After MIL Gleefully Reveals Her Son Went On A Date With An Ex Before Wedding”).
Hmph. It makes me think of when one of my now good friends found out, a couple of years after my first book came out, that he actually did some mild producing for one of the characters in it — my own first love. As I shared some of the story, Shannon started singing a throwback R&B hit that he co-wrote, co-produced, and also recorded before Heather Headley did. The title? “In My Mind” (Heather’s version ishere; Shannon’s version ishere). As life would have it, it was in heavy rotation during the time of that very conversation.
Damn. My book came out in 2004. 2006 is when Heather’s cover of “In My Mind” was released. And you know what? In freakin’ 2023 (November, to be exact), I ran into my first love…again. The brief backstory is we both had separately debated going to a certain restaurant for a quick bite and then saw each other — and being that he has never married and neither have I (because only a guy who hasn’t been married before is personally an option for me), there we went…again…running in the flowers of nostalgia while trying to see if we can figure something out. *le sigh* Then add tax.
Oh, the one who got away. If that’s really how you truly feel about someone, when they do come back around into your space, it can be quite a doozy. And if/when it happens, you may be worrying yourself sick trying to figure out what to do about it. Listen, all I can do is tell you what I’ve learned from my own personal experience and observation of other people’s journeys. Here’s hoping that, by asking yourself the following questions, you, your mind and heart (and body, if it comes to that) will find the answers that you seek.
*P.S. Where’s your journal at? You’re gonna need it.*
Did He “Come Back” — or Did You Go Looking for Him?
GiphySomething that I used to say often is, “If you look ‘him’ up on Facebook, it’s you; however, if you run into him in Kroger, it’s God.” What I mean by that is, whoever you consider to be the one who got away, I’m not sure how “meant to be” it is if you’re only reconnected to him now because you went and sought him out. And no, I’m not coming from the angle that “men are hunters” (I hate that saying) and women should never pursue men (Ruth and Esther in Scripture did; it turned out fine for them — check out “6 Things Church Taught You About Dating That Weren't (Fully) Biblical”).
What I’m saying is when folks shift out of your life and seem to be fine with not reconnecting, there’s got to be a reason for that because they have the same internet that you do. Shoot, even if it’s not something as serious as they’re married if they do think of you fondly on some level, if they really wanted to reconnect, why haven’t they tried?
And here’s the thing — I know someone who once was almost desperate to become someone’s wife. So much, in fact, that she decided to seek out a college ex (sex buddy). He replied to her, eventually they did reconnect —, and although they are “together,” it’s been well over a decade and no ring. Clearly, he wasn’t looking for her or a wife and, as a result of her reaching out, somehow, she convinced herself to settle; now she’s out here believing that she doesn’t want to be married either.
Could it have played out the same way if he had reached out first? Eh, possibly. However, what I have noticed (and no, this isn’t gender-specific) is that oftentimes, the individual who makes the first step is more inclined to compromise than the one who is on the receiving end. That said, this guy wasn’t acting like the human version of Kermit sipping tea while looking out of the window as he wondered how to find her…she did that. And so, since she wanted him, she was more willing to do what he wanted in order to remain in contact with each other. SMDH.
Moral to the story on this one: When two people want the same thing, it’s all good. Oh, but when you convince yourself that settling is better than nothing at all, as writer Maureen Dowd once said, “The minute you settle for less than you deserve, you get even less than you settled for.” INDEED.
All I’m saying when it comes to this particular question is if he got away and he also isn’t taking the initiative to come back, consider why — shoot, why not even ask him? ‘Cause listen, if you took the time to reach out, you might as well get as much intel as possible on the front end. Clearly, he was fine not finding you. Why is that the case?
Did He “Come Back” — or Did the Universe Orchestrate a “Chance” Meeting?
GiphySome of the close-to-day-ones might recall reading another article that I penned for the platform entitled, “Why Every Woman Should Go On A 'Get Your Heart Pieces Back' Tour.” In it, I actually mention my first love and how, back in 2015, we had a run-in. I also said that, after that season, I was over him. Okay, but now it’s 2024, and I just told you that he almost got me AGAIN. I think for me, it’s two-fold. One, he’s never been married, and two, I never go looking for him. It’s always grocery stores or restaurants — random-ish, and honestly, I think because I am such a “signs and wonders” kind of person that is what brings me to a state of “cause for pause.”
Anyway, I think we all can agree that, on a lot of levels, on so many levels, I am an open book. The particulars on this, though, I’m going to keep to myself because I’m still processing some of it (and some stuff is still just my business). I will say this, though: If you are someone who recently had a run-in with your own the-one-who-got-away and you had absolutely nothing to do with initiating it, there are some quotes that I want to encourage you to keep in mind:
“Even if we have ourselves so fully convinced that we are on the right track because we desperately want to believe that the specific direction we have chosen is the ‘correct one,’ if the universe disagrees with our choices, it will not be shy in telling us so.” (Miya Yamanouchi)
“A coincidence will always be a coincidence until its significance is realized.” (Angie Corbett-Kuiper)
“Follow your bliss and the universe will open doors where there were only walls.” (Joseph Campbell)
Does the run-in automatically mean that the two of you are destined to be together? I’m not saying that. What I will say is when you factor in all that happens in the world and how going left instead of right or being 30 minutes earlier or later could’ve prevented you from seeing “him”— yes, the universe is trying to show you something.
Even beyond the guy, spend some time pondering what that could be…, which brings me to the third question.
Is He to Be Your Lover Again — or Is He Just to Show You Something?
GiphyListen, just because I am a marriage life coach and I write on relationships for a living, that doesn’t mean I don’t have my own accountability crew (we ALL need that). The thing that I adore about mine is most of them are just as “straight no chaser” as I am. And so, whenever my first love comes back up, they are always on some, “Can one of you get married already, either to each other or someone else, so we can wrap this thing up?” — and chile, when this last encounter happened, due to some other details of the story, my male and female friends alike were like, “You can’t make this sh-t up!” (you really can’t).
That’s why, I have learned the hard way, to not make some heavy declarations (anymore) until everything really is all said and done.
At the same time, what I will share is because my first love has a tendency to run into me, pour it on thick, and then simmer, this time, I did some real soul-searching to figure out how much of the emotional acrobatics (on my part) was about 19-year-old Shellie still needing to get some things off of her chest more the woman who I am now still being “in love” with him. And boy, was that needed.
Back in 2015, I was pretty much just on, “So, are we getting married or what?!” This time, it was more like, “Why do you keep affecting me this way?” I mean, I get some of why: when your first love is pretty much your first everything, and you are also his first love, the bond is…significant. At the same time, though, because my question was different in 2023, the answers were too.
And the reality is there were still some things that “19 me” needed to work out so that she could catch up to who I am now. And on this side of realizing that, I get just how necessary that was because, first love, some other guy or no (future) husband at all — for myself, I needed to address and respond to some things…within myself.
So yeah, that’s another thing to ask about your own situation: before automatically romanticizing everything and assuming that the two of you are destined to be, ask if he’s to be your now-lover or now-teacher. You’d be amazed how that one question alone can shed a lot of light on what is actually transpiring in this season of your life.
Are the Two of You Supposed to Be Together — or Is There Just Some Closure/Clarity That’s Needed?
Giphy(Side note on this GIF. Erica Ash played the hell out of her role on Survivor's Remorse. RIP, sis.)
There’s another guy from my “get your heart piece back” tour that I reconnected with that I am SO GLAD that I did. One reason is that I carried a lot of, let’s go with the word “burden” of feeling that I made some poor choices (especially when it came to bad timing) that really did cause him to be someone who I filed as “letting him get away.” Another reason is that the way that things ended between us was so abrupt that I always had some questions (he basically called me up one day, said I was like “crack” to him, that he didn’t want to be addicted, and so we couldn’t talk anymore).
And still, another reason is I felt like although things ended, we never really got closure — and yes, something that I am a huge fan of is closure…because without it, sometimes doors are left ajar or cracked and that’s how things can creep right back on in.
The first conversation we had? It was for hours, well into the night. We missed each other. We reminisced about some things. And we caught up. However, the catch-up already let me know that our past needed to stay there because he was divorced, and again, divorced guys aren’t an option to/for me. Some other conversations that followed also brought some closure because, as much as we’ve always enjoyed each other’s company and, quite frankly, as great as the sex used to be (LAWD!), we were two very different people now.
Our values are different. Our experiences have caused us to take different forks on the road. In this season, we desire very different things. You know what, though? I never would’ve known all of that had we not spoken. Yes, some closure was needed, so that I could look back with a clearer and fuller picture.
So yes, that’s why I think another question that should be asked is, if 'the one who got away' being back in your life at this time is so you two can be together, or it’s so that you two can get some real clarity and closure so that the title of 'the one who got away' can be put to rest? Because when it comes to the guy that I just spoke of?
For me, now he’s just a fine-ass man who I had a great connection with once upon a time and who is thriving on his side of the world as I do the same. He didn’t “get away” anymore. He’s gone because…that’s how it should be.
What About Him Being in Your Life, As You Are Now, Would Enhance It?
GiphyI am very word-specific and word-literal. That’s why I want you to notice how, with this question, I didn’t say “change” or “improve” — I said ENHANCE. To enhance is “to raise to a higher degree.” Some synonyms for enhance include build-up, strengthen, increase, add to, and complement (check out “If He's Right For You, He Will COMPLEMENT Your Life”).
You know, several years ago, I was on an interesting journey with a guy, and I’ll never forget what two of our friends (who were married at the time) said when they found out: “Shellie, I see how you’d be good for him. We’re not sure how he’d be good for you, though.” HMPH. Y’all better listen to folks who care about you when they speak into your life — there’s no telling what they can spare you from if you just choose to listen.
And that’s the thing — the one who got away, even if he was awesome for you back in the day, even if it’s totally your fault that he got away the first time…who are you now? Would bringing him back into your world, on any level, enhance it? Would it really? And, if you do truly still care about him, would you being back in his life enhance his as well?
Because there really is such a big difference between being good to someone vs. being good for them (check out “Question: Is The Man In Your Life Good 'TO' You? Good 'FOR' You? Or...Both?”) and mature folks? They don’t want the former if it doesn’t come with the latter — mutually so.
BONUS: Please Don’t Mistake Nostalgia for Love
GiphyI rememberonce reading that our brain actually craves nostalgia.Some research says that taking walks down memory lane can give us a greater sense of self, put us in better moods, and it can even play a pivotal role in our personal growth and development. And y’all, that may be why we sometimes get so caught up when it comes to (certain) men from our past. Nostalgia can be so seductive and even exhilarating that we might think it’s love when…it might just be an emotional high for the moment.
Real conversations. Slowing down. Praying, meditating, and journaling. Not being quick to jump into bed. Letting some people you trust hold you accountable. Being honest about what you need at this time in your life. Not living in the past if it’s at the expense of compromising your present or sacrificing your future. Encouraging “him” to do all of these same things for himself as well — this is what helps you to come to the realization of whether what you’re feeling is nostalgia, love, or both.
And if it is love, is it the kind of love that needs to have a commitment attached or a full and final release?
___
Yeah, whether it was bad timing, he was the wrong person, or a little bit of both, the thing about the one who got away is they did so for a reason. If they’re back, see what the PURPOSE is in that….so that if they stay, they stay for good. And if they go, they’re gone for good (preaching to the choir here, by the way).
Feel me? I certainly hope you do.
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Featured image by Adam Hester/Getty Images