Trivia Answer
Most of you who replied correctly identified the TTC’s two zone fare system as the crux of this person’s problem. To go the most direct route (bus to Luttrell loop, transfer to Danforth streetcar, transfer at Woodbine station to Bloor-Danforth subway, transfer at Keele station to Bloor streetcar, transfer at Jane loop to the 50 Kingsway bus) our poor stranded traveller would have to pay three fares (at Luttrell and at Jane). Is there a way around this? Yes, in theory.
Grab an eastbound bus, preferably 67 Pharmacy, and take it to Ellesmere Road (the Pharmacy bus travels along Warden at this point). Transfer to 95 York Mills and take this bus to Glen Echo loop. Transfer to the 96B Wilson bus and travel along it until you get to Islington, and then transfer onto 37 Islington and ride that until you get to Bloor Street. Ironically, that’s fewer transfers than it would take to go the most direct route.
I say “in theory” because by the time you get to Glen Echo loop, the driver of the 96B Wilson bus is going to give you a funny look if you present him with a Pharmacy transfer. You would do well to explain your situation to the driver at this point and request a new transfer, because if you didn’t get a funny look from this driver, the driver on Islington would probably order you off the bus.
David Cavlovic came the closest to answering this question correctly.