If she were just a shy girl as he had thought, then it would be much easier to tease her and to get a little closer if the situation allowed for it.
He was the type of person who believed that he pushed hard enough and made the situation favour him more than he could get what he wanted.
If a shy or distant girl were more aware of their surroundings and did not want the bad attention on her that could follow her around, then it would make things easier for him, as it would be more difficult to avoid him and reject him whenever they were in public.
By drawing attention to the mask, it made more people just as curious about what was hidden beneath it.
If there were enough to support him, then it could become easier to use peer pressure to make her reveal her face to everyone.
If she was too uncomfortable showing everyone, then he could convince her that he would be willing to overlook it if she revealed her face only to him in private.
