WARNING: The following contains spoilers for Naruto: Shikamaru's Story - Mourning Clouds by Takashi Yano and Masashi Kishimoto, available in English from Viz Media.
In the Naruto series, Shikamaru was infamous for saying the wrong things at the wrong time. He often slipped up, calling Naruto lazy, and even accidentally insulting Sakura over how she treated Naruto. When it wasn't accidental, it was all in jest, of course, as knowing how laid back Shikamaru was, no one really took him seriously.
Come Boruto, though, he's older, wiser and helping Naruto perform his duties as Hokage. Therefore, one would think he's matured on this front. Unfortunately, in Naruto: Shikamaru's Story - Mourning Clouds, his knack for running his mouth and being too casual gets him in trouble once more as a colleague accuses him of sexual harassment.
It happens weeks after he senses war on the horizon with the Land of Earth, who want to invade the Land of Flowers. After a breakdown at the meeting of the Kages, Shikamaru's dead certain the Mizukage of Kirigakure, Chōjūrō, is being manipulated by the Tsuchikage of Iwagakure, Kurotsuchi, to invade for the Flowers' resources.
As a result, Shikamaru has Rō and other spies in Iwagakure sussing out details in an attempt to protect the peace Naruto created after the Kaguya War. He speaks with Hinoko on the mission and she admits there's a lot of shady movement, hinting an invasion will happen. As he watches families playing at a park, all because he's sick of the office, a weary Shikamaru then makes a big mistake by telling her she should start a family.
"'You should start your own family, Hinoko,' he said. 'You're old enough to be a mother already. Not that it wouldn't be a loss for Konoha if you stopped working.'" It's a sentimental moment wherein he tries to bond with her. The problem is, a man shouldn't be commenting on a woman's life like that, especially in regards to motherhood. Shikamaru doesn't know her wants or circumstances so it's definitely crossing a line. Hinoko tells him straight-up that this is "sexual harassment," leaving him bemused at first, only to realize he had indeed objectified a woman's body and judged her purpose in life.
Hinoko knows Shikamaru meant no harm, so she lets it slide, knowing he gets the picture. There's no lengthy exposition needed to make him uncomfortable. They discuss the rest of the mission and how to go about gathering secrets and intel for Naruto, but he brings the incident back up at the end, as he feels bad about it
"'Forgive me for the sexual harassment?' he asks. She replies, 'I'm, like, filing a suit when I get back,' sticking her tongue out and teasing him." She knows Shikamaru is a good guy and, lucky for him, they've got a sibling-like relationship where they can discuss these things and apologize without any harsh judgment.
