Most Helpful Guy
If I REALLY thought it could work, and the travel was worth it, and that she'd be willing to travel to my area... probably an hour. Say 25-35 miles.
Right now, 25-30 miles is kind of a rule of thumb for driving. It's really far (for me, anyway); I would have to figure that I would try to be in that area for over 2 hours to "make up" for the time on the road; if I'm going an hour or two away, and it ends up being a 30 minute date, or she just doesn't show, I'd be more ticked off. So I try to stay in some area for at LEAST the amount of time it took to get there; if not the time It'd take to get there AND back.
Other things figure in, though, like road conditions, weather, time, etc...
Most Helpful Girl
A few years ago a guy flew from Australia to the Eastern US for a date... that lasted for a week... probably not considered a date but it was fun.
I'm not sure how far I would drive for a date if I were to ever date again. Dating can be such a pain in the butt.