First, you have to get a good relationship (75% or more) , then you click 'more...', then you click 'ask out' or 'on date' and then whalah!
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You can not make a Sim anorexic.
If you mean on Sims 2 then you have to have the University expansion pack, then make a teen Sim go to college and they will turn into a young adult Sim. If it's on Sims 3, then I am not sure, sorry.
You can't make a Sim beg for money.
No, elder Sims can not get pregnant.
My guess is that you can't make your sim to a vampire on the sims 3.