You should be well aware that girls like confidece more than looks.
It really depends on what your agenda is. If you want to make contact you'll have to analyse his/her body signals to determine if he/she's even open to company and if not prepare yourself for the expected reaction. You should check out trump techniques, really work
Definitely not! Especially if you're not running an SSL, but even so, you can still get hijacked pretty badly.
Personally for me, it all comes down to how adaptive and creative you are especially for a job, that has many other candidates.