Issa Rae and Kendrick Sampson get cozy in Los Angeles while filming the final season of Insecure

Issa Rae and Kendrick Sampson get cozy on a bench in Los Angeles while filming on set for the fifth and final season of Insecure

Issa Rae is back filming the fifth and final season of her hit HBO show Insecure. 

On Wednesday the 36-year-old actress cozied up next to co-star Kendrick Sampson, 32, as they shot a scene on a city bench in Los Angeles. 

One of her many love interests in the show, Sampson was seen with his arm around Issa’s shoulder as they teased a potential romantic rekindling in the upcoming season.

Insecure: Issa Rae, 36, and Kendrick Sampson, 32, film a scene from the fifth and final season of their hit HBO show Insecure as they cozy up to each other on a Los Angeles bench, teasing a potential romantic rekindling between their characters

Issa was seen in a stylish tan Danielle Cathari x Adidas track suit and a pair of orange heels as she rested her head on Sampson’s shoulder. 

He looked equally as sport in a pair of maroon basketball shorts and a button down with a pair of untied sneakers while holding a dog, as they exercised a range of emotions while in scene. 

In the final episodes of season four, his character Nathan told Issa that he was bummed to hear that she had rekindled her romance with her longtime on-off boyfriend Lawrence. 

Short of a happy resolve between Issa and Lawrence (played by Jay Ellis), he revealed to her that not only was he thinking about taking a job in San Francisco but also that his former girlfriend Condola was pregnant with his child. 

Missed connections: Season four left fans with many unanswered questions between the pair's romantic resolve

Missed connections: Season four left fans with many unanswered questions between the pair’s romantic resolve

Viewers were left with many unanswered questions during the June season finale, with many cliffhangers surrounding the fates of additional show stars Yvonne Orji, Natasha Rothwell and Amanda Seales. 

The fifth season began filming on January 21 as Rae posted a photo from outside her trailer, and said, ‘First say of Season Bye-ve.’ 

Speaking to Deadline about the conclusion of the show she both stars in and co-created she said:  

‘Prentice [co-executive producer] and I are so grateful that HBO believed in our show from the beginning and kept faith in us to see our vision through the end. We always planned to tell this story through five seasons, but we couldn’t have made it this far without the tremendous support of our audience.’ 

The show snagged three nominations at the 2020 Emmys, including Outstanding Comedy Series and Lead Actress in a Comedy Series. 

End of an era: The hit HBO show began filming on January 21 after Deadline confirmed that this would be the final season just one week prior

End of an era: The hit HBO show began filming on January 21 after Deadline confirmed that this would be the final season just one week prior 

Despite losing to Schitt’s Creek which cleaned house at the award show, the cast was in good spirits as they watched the show from their virtual viewing party at the SoFi Stadium in Inglewood – a location centric to much of the show’s filming.  

Sampson has been a leading voice and face in the Black Lives Matter movement, with his organization BLD POWR organizing peaceful protests all over Los Angeles.

The organization aims to dismantle racism in entertainment and ‘organize Hollywood around social justice issues,’ as he told Interview Magazine in September: 

‘As much as I’ve always dreamed of being the lead in massive films and winning awards, at the end of the day, that’s not my purpose. At the end of my life, I want to be able to say that I did all I could to leave this world better than I found it. That is the end goal.’

The new season of Insecure is set for release in late 2021.   

Closing the chapter: 'We always planned to tell this story through five seasons, but we couldn't have made it this far without the tremendous support of our audience,' Rae told Deadline; pictured with Sampson on September 20

Closing the chapter: ‘We always planned to tell this story through five seasons, but we couldn’t have made it this far without the tremendous support of our audience,’ Rae told Deadline; pictured with Sampson on September 20