From her old-fashionedness maybe? I mean, she didn't own a tv iirc. In 2004.
Magus in general are behind the times with technology. I think Rin's ineptitude was brought up a few times in the VN (maybe), but it became a recurring joke in HA. Also, the OP is retarded. Rin never did anal once.
Rin and Saber challenged the dick. The dick destroyed them.
There's always the hidden Illya route
Her family is very old fashioned. Shirou himself is not a very modern person, he didn't own a cell phone or anything really, but even he thought Tohsaka was old fashioned compared to him.