I ride with a 77 year old man, who can (and does) obviously make his own choices. However, back when we started a few years ago, and he mentioned to his daughter (who was my age, mid-50's) that he was riding with me on a loaned bike, she thought he was crazy. After a few months, and seeing how her dad enjoyed the activity, and that he was doing it safely, they bought him his own bicycle for Christmas.

So, in short, do you know (or can you get to know) anyone who rides and has a bike to loan that you could ride with? That could be an interesting path... even if it is not a great loaner bike, it could break the ice.