I think that whichever of you (bike or Gary) is most likely to have a coronary is the one that ought to lose the weight. We can only ride as long as we are alive, ya know. But that should not stop you from getting another bike, or two. To quote another member, the correct number of bikes to have is n+1 where n is the number you have now.
Tim
P.S. If you get a bike that "... fully loaded (water, keys, cell phone, etc.) weighs 18 pounds" (i.e. 33-15) I trust you plan to bring lots of $$$