Sure, why not? Saturday morning I had someone approach me at the gas pumps asking for $5, gave me some sad story about a sick relative and being en route to hospital and ran out of gas. Five hours later in a town 37 miles away from the first one, I had someone approach me at a different convenience store asking me for $5 for gas, and I'll be darned if they didn't also have a sick relative and encountered financial hardship while on the way to hospital! Sunday I had a guy approach me at the grocery store asking if I would buy his Food Stamps card so he could have money for bus fare to get to NYC to visit a sick relative...
You can't make this stuff up, which makes it totally believable to me that he could have encountered more than one person needing a ride. I haven't seen anything stating that both encounters were identical in nature, so Barefoot Guy and Casual Acquaintance Guy could certainly be two discrete encounters with only Casual Acquaintance Guy getting an actual ride.