After she beats his ass up, he manages to grow closer to her incurring her pity, showing his bruises and blood to everyone in the camp. He does manage to grow closer, but she just sees him as a little brother. He has no experience and zero appeal, so he can only scheme and even after he forcefully inserts his finger into her pu*sy and he gets scolded, he continues to scheme.

Seeing as he was unable to convince her, he outright asks for it, like usual. As expected, she rejects him and he goads her into making a bet on fighting. He was confident and I thought he'd finally show a cool side, maybe he improved his stats or something, but no no no, instead, he just decided to be pathetic again and bank on the girl's refusal to hurt him. He just let himself get beat up over and over again until she took pity on him.

It was a completely pathetic approach and all throughout, I was sincerely hoping he wouldn't succeed because it's totally undeserved. But alas, the author has no intention of making him grow as a person or even make him just a tiny bit more likeable. I couldn't even read the scene afterwards and ended up skipping it. Good thing, too, because the scene with her has the longest chapter of the series. Seems the author really like this love interest. Should've tried harder if he liked her so much.