MeetWays
Making plans with cross-town peeps always involves the offer "let's meet halfway" -- laughably hollow, because it's easier to just drive to the guy's house than figure out where the hell halfway actually is. To make the lie a reality, use MeetWays.
MeetWays also has partnerships with car rental companies and hotels -- once you find this magical center-point, it might take you several days to find that your date's personal mythical location doesn't in fact exist.

