'Insecure' showrunner Prentice Penny teases series' final season, why fans may not be “satisfied” with ending

e_prenticepenny_justinamintz_102021
HBO/JustinaMintz

Prentice Penny is sharing details about the fifth and final season of his hit HBO series Insecure.

After the season four finale left fans wondering whether main characters Issa and Lawrence could possibly ever get back together after Lawrence revealed that he accidentally impregnated his ex, Penny says it’s unlikely that fans will be “satisfied” with Issa’s relationship choices.

“They’re all going to feel like, ‘I want her with this person for this reason,'” Penny tells ABC Audio.

The showrunner admits that Issa’s love life was also a topic of “debate” in the writer’s room, noting that a happily-ever-after ending wasn’t necessarily on their agenda.

“We just tried to tell the most interesting story regardless of that and…not…let that weigh in too much,” he says.

While season five may not end with the perfect relationship pairings for fans, Penny does promise that the final season will offer “personal growth closure” for its characters.

“Not necessarily closure of the end of their story,” he explains. “Because one of the things that we kept getting tripped up on…was like, ‘How do we land the plane?’ And it was a lot of pressure…especially at HBO, where…a lot of finales get super scrutinized, like Game of Thrones and The Sopranos…where…people [are] like, ‘Why did they do this?'”

Pressure aside, Penny teases that the finale episode will be the perfect set-up for a continuation.

“We…realized…that the characters lives will continue, it’s just we’re not following them,” he says. “So we… started to ask the question, ‘Well, if we were doing season six, what would be an interesting place to start… from?” And that became…where we should end the show.”

Season five of Insecure premieres Sunday, October 24, at 10 p.m. ET.

Copyright © 2021, ABC Audio. All rights reserved.

53e68-dance-9

Bend Community Contra Dance

Bend Community Contra Dance: Live traditional music and couple dancing akin to square dance. Come solo or bring a partner to join in the fun. Beginners welcome! Saturday 11.09.25 6:45 to 9:30 $10/person Band: Fiddler Darin Gentry

sting301710174758

STING 3.0 Live at Hayden Homes Amphitheater

Sting is set to captivate audiences with his “STING 3.0” Live Tour at the Hayden Homes Amphitheater. This highly anticipated event promises an unforgettable evening filled with the iconic sounds that have defined his illustrious career. Fans

neavetrio4_byarthurmoeller

HDCM Concert Series: NEAVE TRIO

Friday, April 18, 2025, 7:30pmUnitarian Universalist Fellowship of Central OregonConcert Sponsor: Drew Family Dentistry This Grammy-nominated group has earned enormous praise for their engaging, cutting-edge performances. Gramophone has praised this Boston-based group’s “taut and vivid interpretations,” while

scaled_768-18

Wildlife Trivia at The Lot

Think Wild Trivia Nights are back this winter! Test your knowledge of local wildlife, outdoor recreation, conservation news, and more! Support Central Oregon’s wildlife hospital, win fun prizes, and enjoy delicious food and beverages at The Lot!