I've had social meets like this, granted not many but they've still happened. Sometimes the guy has just wanted to see how comfortable he feels with a prostitute, sometimes he just feels odd going straight in for the kill - after all society brings us up to expect to get to know a potential sexual partner. It's always been fine but I do apply my usual screening and security rules and do go along knowing there's a risk it could be a set up. I chose somewhere not to far away, and always get the fee within the first 5 mins - they've always brought it in the form of a card with the cash inside, which I've been able to discretely check.

It depends on where the line is between 'unusual' and 'odd' for you. If you're not comfortable, because it's the latter, it's unlikely to be a good experience for either of you.

If you are worried about being scammed, have a search for 'deposit' here to see some other ways to get money up front. With Amazon vouchers, all the sender needs to know is an email address, not bank account details, for example.