Is it....

[Subotan]

I don't mean this in a nasty way, but if you never get the initiative to be able to decide things like this on your own, you're not going to get any of the experience and, crucially, confidence for getting a girlfriend let alone a proper relationship.

Look at the case study you're talking about. So, you haven't seen her for seven years, I'm assuming you used to be friends, she's single, she's cute; why would you even think twice about whether or not it's "OK"?!? Sure, the way you actually go about doing it you should definitely think about, and going to the mall seems like a good idea, but seriously this should be a no-brainer.

EDIT: Now, actual dilemmas (I'm not giving an example, as you'll know if you're in one later in life) are a different story, but you're better off talking about that with your closest friends than guys on the internet.