aside from other issues that make him sound like a creep...

I just stepped down from presidency of a bike club. The liability thing, coupled with how your insurance policy is written, is a very real issue for organizations. Who hosts a ride, where you host it, what you call it, whether you charge for it all that can factor in to whether your liability coverage will ( most likely) be in effect. I'd put my money on the ride changing from a "shop ride" to a "pickup/informal" ride to try and work within a policy.

IANAL, YMMV etc.