Wow, thanks for even more great advice guys. I really appreciate all you given me like the experiences, the words of caution (I agree you can't be too trusting nowadays), the humour, and even those two free psych consults. A backbone is now on my xmas list. :)
I'll tell you all how it went today. I figured the sooner the awkard possibility of pissing him off and alienating myself from the rest of the team, the better. I explained to him how its just too out of my way and how it wouldn't even be feasible the times when I need to give my mom a ride to her work. Happens about 8-10 times in a month. We'd be canned in no time that way. Then, I just came out and said I've looked at the city's bus routes and if you can take the number __ bus and be at this drop off by this time, I'd gladly give you a ride. He may have to wait a little on the days I drive my mom but its got an avondale and a lunchbox/coffee shop right by it. He agreed fairly quickly. I think he's just the kind of person who'll try to get as much as they can but will take whatever they can get without any real strong emotions one way or the other.
Overall, I'm very happy with how things went today between me and Shane. Thanks again to everyone.