Because of being dumped, cuckolded, etc. in love with girls, he has completely lost faith in love. He doesn't dare to love another girl even if he is a flirt.

During a play session filled with confidences between him and his friends, including you. He told everyone about his unfortunate love life.

Suddenly he turned to look at you, like he just had a bright idea

"Hey bro, or should I try to like you? Who knows, it might be interesting"