@brandon definitely not before or during helping, but once someone is no longer in a state of dependence on you and they can be honest with you without you jeopardizing their pc or account etc, sure. Obviously in a professional and respectful way, whether it's friendly or romantic. At the end of the day we're all human beings.
@Gina I like this answer. IT's got that sort of power dynamic when someone needs help and comes to us in that state of (sometimes) helplessness. I can easily see how someone might worry that their laptop or account may be compromised if they don't accept the advances an IT folk may make