Based on my experience as a motorcycle rider training instructor, the best thing we ever tried was a class of all women for getting the ladies into riding.

We found that many women were hesitant because it was a stereotypically male passtime. The consensus seemed to be that they didn't want to be seen as weak or incapable infront of guys or were worried about prejudice from the males in class.

We did some test classes of all women at a bike show one year (about 15 ladies at a time) and they were some of the fastest, strongest, best behaved, and funnest classes we ever ran...surprised us all actually. I'm not teaching anymore but I heard that they're going to be trying the same thing with the 'over 50' crowd. I bet there will be similar results.

In your example you're talking about a single person so this might not apply...but it's still food for thought if the opportunity comes up.