Is the bike well fitted to the guy?
Having helped a few dudes like this, doing work on their bikes to make them rideable and useful, and getting them a lock only for them to not even bother to use it, then complain that it takes over an hour to go to work because they're back on foot...
It's as if you pick them up and dangle their feet in the air, but they don't bother to grab on to anything and then ***** at you for having let them go. Some people just don't want to help themselves.
It's also why I haven't done this in a while, but I find this thread refreshing to see this guy dosen't sound like that kind of person.