As long as the roof you have is not leaking, it doesn't need replacing. If you want to replace it anyway, make sure you update your homeowners policy to show that. The older home doesn't mean older roof. You might ask the seller of the home when the roof was last put on. A roof should last about 10 years or so.
Ask her if she needs more underwear, then when your shopping ask her if she wants underwear with 'Hello Kitty' or some kind of cartoon she likes. Then if they have a pack with training Bras, and underwear, then slip it in the cart. When you get home and she asks why there are bras in the pack, then tell her that it wouldn't be an outfit if she didn't wear both, and that it's like wearing a bathing suit under your clothes.
Tell her the time, then walk away. If she asks about buying sex, tell her no as she could be an undercover cop.
If he asks you out.
Hamlet asks Horatio to, "tell my story"
Just could mean he needs to say something important such as some sort of private discussion he feels he needs to tell you about. If anything, whether it's something relationship wise or something else, go ahead for it, at least he trusts you some sort of way to tell you something. If he doesn't tell you something as far as it coming to liking you, I wouldn't worry about it.
Tell her a joke.
He asks if you have a bofriend.
when he asks "will you go out with me"
Tell him the truth.
He asks you out!?
Of course you can.
Tell her the truth. What else could you do? Tell her why you like her!