That's great you want him riding! You are right a better bike would probably help. Most of us would agree that it would be probably be best for him to pick the bike he is going to ride. Maybe the cost will make him more serious about keeping it up? Anyway, if you are going for a Trek you might consider the FX. I think it is a little more "manly" while still having a more "comfort." I would at least have his inseam measurement for the LBS to go by.
If you are going for the least expensive Navigator then the FX would cost you more...
http://www.trekbikes.com/us/en/bikes/bike_path/fx/71fx/



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