2. We was fifteen when he went to the Surface, and there has been a sad shortage of dwarf girls since then. The time between "girls have cooties" and "oh crap I'm a Surfacer" was spent being generally obnoxious to girls, and while he managed to steal a few kisses he never actually slept with anyone.
3. Yes. He would probably think he was, but in reality he would be a loud, tomboyish, overflirtatious one.
4. He doesn't like the idea of pets very much, but if he could get his hands on a saddle for a Mabari hound...
5. Himself. Since coming to the surface, though, the attention-starved dwarf tends to exalt anyone who seems to care about him; right now Tobias is as close to idolization as it could get.