How do you know when it is appropriate to ask a guy out to dinner to make sure you won't be rejected especially if you work for the same company and you don't want an awkward situation?
Dinner for first date, when you are asking him out, might be a
little much. Try lunch first, or drinks after work. Keep the first
"date" inexpensive and open ended - less chance of rejection. I'm a
guy, and I would feel a dinner invitation from a girl that I may be
interested in, may sending me the wrong messsage as to her
intentions, and may be too much of an event for the first meeting.
Certainly dinner is appropriate for the second date, and he will
probably be asking you to dinner instead of vice-versa.