Our intrepid dream weaver Sebastian Terry will go to extremes to help others achieve their goals. Terry had once skydived naked—it was on his own 100 Things list—but he’d never gone skydiving with a 77-year-old woman and her grandson before. In Episode 5 of our go90-exclusive series, that’s exactly what happens.

“Cody is a cool, all-American guy who just wanted to do a really nice family thing,” Terry explains. “And his grandmother, who is now well into her seventies, had been a champion female skydiver, once holding the world record for most skydives by a woman. But on her last jump, she had unfortunately broken her back, decades ago, and she’d never dived again. Cody’s life-long dream was to skydive with his grandma and somehow he talked her out of retirement. Cody, ‘Tutu’ and myself got onto a plane, go way up there and we jumped together. It was just awesome for me to do it again, with my clothes on this time, and help these two people recreate a very special family bond. But they were also so stoked to take the jump together. Let me tell you, she’s a total badass adventuress. She had white hair and the works, but it just all came back to her.”

Watch a teaser below, then check out the full episode on the go90 app!