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The Final Season of ‘Insecure’ Will Arrive in October

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Insecure is set to return with more mirror raps, polarizing love triangles, and awkward moments. But unfortunately, all good things must come to an end—HBO announced that season 5 will be the show’s last.

Lawrence and Issa

Courtesy of NetflixNetflix

Insecure‘s season 4 finale ended with a jaw-dropping cliffhanger. In an unexpected twist, Issa (Issa Rae) must decide if her relationship with Lawrence (Jay Ellis) is worth fighting for as he finds out his ex-girlfriend is pregnant. The season also ended with Molly (Yvonne Orji) and Andrew (Alexander Hodge) breaking up. As Issa and Molly hit rock bottom in their relationships, they realize how much they need each other—meeting at a diner to (hopefully) reconcile.

Here is everything we know about the upcoming final season of Insecure.

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The series will end with season 5.

HBO announced that Insecure would end after season 5. Amy Gravitt, the network’s executive vice president of programming, told Variety, “The show is as incisive as it is heartfelt, and it has resonated strongly with its audience because of the deeply personal work that Issa, Prentice, Melina, the cast, and the writers have put into it. This talented team has conceived a brilliant final season for Insecure, and we look forward to having many more stories to tell with this singular group of collaborators.”

At the 2021 NAACP Image Awards, Rae took home the Outstanding Actress in a Comedy Series for Insecure. After winning, Rae spoke to Entertainment Tonight about preparing to end the show. “I’ve been wrapping my head around this since, candidly, season 3,” the actress said. “But I’m so grateful to be able to play this character, who is obviously a version of me, and in the same way that I want this character to grow, I want to be able to grow too. So I think that’s what comes with it—I’ve played her for a long time, and I have so much more that I want to do.”

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The cast and crew have finished filming season 5.

Rae took to Instagram to announce that she and other castmates have finished filming season 5. Rae posted a gallery of photos with the Insecure crew celebrating the end of the show. “WRAPPED a show I’ve been writing for eight years and shooting for 6, surrounded by a chosen family of incredible creatives,” Rae wrote in her post.

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Orji also took to her Instagram to share a heartfelt message to Rae and the Insecure cast and crew. She posted a ray of photos of her last day onset and an intimate video of her giving a celebratory speech that made her and Rae shed tears.

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According to Rae’s Instagram, season 5 was in production in January. She posted on Jan. 23: “First Day of Season Bye-ve #InsecureHBO.”

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Rae also talked to Entertainment Tonight about her feelings about the last season. “Being on set every day, I’m definitely taking it all in on a different level now, just in terms of, ‘Wow, I love this family. This is my family.’ And we’ve done so much, and these people are incredible, and I feel so blessed to work with them,” Rae said.

Insecure’s Instagram account also posted a group selfie of the girl gang reunited on set in late February. “We love to see it. 😍 What are your season 5 predictions? 👀 #InsecureHBO,” they captioned the post.

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The majority of season 4’s cast will likely return.

It’s expected that the core cast will return for the final season. The girl gang—Issa as Rae, Orji as Molly, Natasha Rothwell as Kelli, and Amanda Seales as Tiffany—posted photos on set, along with Jay Ellis, who plays Lawrence. The return of Andrew, aka “Asian bae,” is uncertain after his and Molly’s breakup in the season finale.

molly and issa walking in la

Molly and Issa walking in LA.

Courtesy of NetflixNetflix

According to Popsugar, Nathan (Kendrick Sampson) is also coming back. In season 4, Issa friend-zoned Nathan after reconciling with Lawrence. But even though Issa and Lawrence reunited, Nathan still wants to be with Issa, and the season finale left things unclear about the future of Issa and Nathan’s relationship. On Feb. 11, fans got a tease of what to expect in the last season as paparazzi photographed Issa and Nathan cuddling on a city bench, sharing a laugh.

Season 5 is set to premiere in October.

HBO announced that season 5 of Insecure would air later this year in HBO Max’s lineup trailer. According to the show’s official Twitter account, Insecure will premiere in October. “The wait is almost over the final season. October 💜,” the post reads. Fans will also get more than eight episodes, Rae confirmed to ET.

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Rae wrote season 5 during quarantine.

Rae kept herself busy in lockdown as she spent her days working on the season 5 script. On the Variety After-Show in May 2020, Rae talked about her experience planning the final season virtually. “I think we have a really good room where people are very, like, sensitive to people speaking. We implemented a hand-raising policy just because. That’s the other hard part, like we’re such a jokey room, and it is hard to get in there with the jokes. So we’re finding our rhythm, but it’s still really fun,” the actress said.

Kerry Washington will be in the director’s chair again.

Washington is not a new face to the Insecure crew: She joined the family in season 4 and directed the “Lowkey Trying” episode, which won an Emmy for Outstanding Single-Camera Picture Editing For A Comedy Series. As the episode aired, Washington live-tweeted with fans about the episode. She said it was her dream job and that she’s been a fan of the show for years.

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The Little Fires Everywhere star will take the director’s seat for another episode for season 5. She announced her return in an Instagram video featuring a Instagram Live snippet of Rae and Orji sharing their experience working with her. As the snippet fades out, Washington appears in the video with her directing credit on the cover of the episode five script as “Without Me” by Eminem plays in the background.

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As Rae prepares to turn the page on a significant chapter in her life, she has more projects on the way after signing a five-year deal with WarnerMedia. Rae is currently working on a new series called “Rap Sh*t” that follows two rappers living in Miami, an adaption of Brit Bennett’s bestseller The Vanishing Half, and more that will be featured on HBO and HBO Max.

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Jennifer Lopez Joined Ben Affleck In L.A. With Kids For Thanksgiving

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Jennifer Lopez Joined Ben Affleck In L.A. With Kids For Thanksgiving


On Wednesday night, Jennifer Lopez arrived in Los Angeles with her 13-year-old twins Max and Emme. The family was likely there to join Lopez’s boyfriend, Ben Affleck, for the Thanksgiving holiday. Lopez recently returned from the much colder climate of British Columbia, Canada, where she was filming her latest project, The Mother.

J. Lo touched down in her private jet wearing a teddy fur coat from Coach’s Autumn/Winter 2019 collection, and a pair of Ugg boots. Classic airplane outfit, celebrity style. Lopez and Affleck originally dated in 2002 and broke up in 2004. Their romance was rekindled earlier this year, soon after Lopez ended her relationship with baseball player Alex Rodriguez. The new couple went official in July, while celebrating Lopez’s 52nd birthday abroad.

Affleck’s most recent relationship with Ana de Armas ended in January after about a year together. He had divorced ex-wife Jennifer Garner in 2015 after being married for almost a decade. Garner and Affleck had three daughters, Violet, Seraphina, and Sam.

Before traveling back to the U.S., Lopez posted a story to Instagram Reels about how grateful she was to be headed home.

“Hey everybody, it’s my last day here shooting on The Mother out in Smithers in the snow, it’s been beautiful, but tonight I’m on my way home,” she said, as she walked through the wild landscape in a black coat and beanie.

“I’m so excited for Thanksgiving! I hope everybody has an amazing weekend with their families and their loved ones, there’s so much to be grateful for this year. I’m on my way!”

This is the first major holiday of the year since Lopez and Affleck reunited, so it’s likely to be a big one for both families.

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Everlane’s Black Friday Sale is Packed With Winter Essentials

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This is not a drill: Everlane just kicked off its Black Friday sale. Now through Monday, November 29, the direct-to-consumer brand is offering 20 to 40% off its cozy sweaters, minimalist activewear, and popular jeans. If you’re not super familiar with Everlane, let me spell it out for you: this is a big deal.

The e-tailer might be known for making sustainable, ethically made clothes and accessories at a fair, affordable price, but Everlane rarely has sales beyond its Choose What You Pay section. So, if you want to stock up on cute basics for less, now’s your time to shop.

And, in true Everlane fashion, the brand is taking this opportunity to give back. Everlane is partnering with Rodale Institute and help U.S. farmers transition their farmland to regenerative organic—and donating $15 per order to the cause. A great sale that gives back? I’m sold.

But, hurry! These deals are going to sell out fast, so you won’t want to waste any time filling your e-cart.

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1

The Cloud Turtleneck

$150 $105 (30% off)

Sweater weather is officially here, so why not pick up a few fresh layers? This turtleneck is the S’s: snuggly, stylish, and on sale. 

2

The Authentic Stretch High-Rise Skinny Jeans

everlane

$78 $58 (25% off)

Looking for a great pair of jeans, minus the markup? Everlane’s classic skinny style is not only super stretchy, but it’ll look good with everything from chunky sweaters to silky blouses.

3

The ReNew Teddy Slippers

everlane

$65 $39 (40% off)

Why limit the shearling trend to the upper half of your body? These plush slippers will give even your most worn-in sweats a stylish edge.

4

The Chunky Cardigan

everlane

$110 $77 (30% off)

Sure, this may not be the cardigan Taylor Swift was talking about. But, with an exaggerated collar and ribbed finish, this style would definitely score top marks from the singer herself. 

5

The Canvas Utility Boots

everlane

$115 $59 (40% off)

Brave the cold weather in style with Everlane’s chic boots. The canvas uppers and thick sole make these an ideal, all-weather option.

6

The Lofty-Knit Henley

everlane

$150 $105 (30% off)

Made with a nubby blend of merino wool, alpaca, and recycled nylon, this henley is perfect for a cozy night in, yet stylish enough to wear in public.

7

The Perform Bike Shorts

everlane

$45 $22 (51% off)

No, you can never have too many stretchy pants. Everlane’s bike shorts ooze major Lady Di vibes — for under $25, no less.

8

The ReLeather Court Sneakers

everlane

$110 $66 (40% off)

Made with recycled leather, these refresh sneakers will serve up major curb appeal — and Mother Nature’s seal of approval. 

9

The Field Dress

everlane

$100 $60 (40% off)

Found: a fun, flouncy frock you can wear year-round. For a wintry take, pair with opaque tights and your favorite chunky boots.

10

The Cozy-Stretch Wide-Leg Sweatpants

everlane

$150 $75 (50% off)

With a straight-legged silhouette and wool material, it’s safe to say these are the chicest sweatpants we’ve ever seen. To sweeten an already enticing offer, this pair is half off.

11

The Organic Cotton Flannel Popover

$80 $56 (30% off)

Everlane reimagined the traditional flannel with a cropped silhouette, voluminous sleeves, and a slew of minimalist colors.

12

The Studio Bag

everlane

$275 $192 (30% off)

Large enough to fit all your essentials, but not too big that it’ll weigh you down, Everlane’s Studio Bag is the perfect everyday purse.

13

The ReNew Long Liner

everlane

$158 $118 (25% off)

House Stark was right: winter really is coming. Made with recycled materials, this liner is a great layering piece that’s considerably chicer than the yesteryear’s Michelin Man-worthy parkas.

14

The Felted Merino Beanie

everlane

$50 $30 (40% off)

All set on clothes? Pick up this cheery beanie, which is 40% off its original price.

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29 Winter Fragrances That Exude Main Character Energy

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29 Winter Fragrances That Exude Main Character Energy



29 Winter Fragrances That Exude Main Character Energy

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