I told several friends that I was getting a Diva Cup a few months back, and both they and I were a bit, uh... horrified with the idea, but I decided to take the dive. Three cycles later, I am absolutely in love and could not imagine a cycle without my cup or with itchy, leaky pads. I continue to insist to my neighbour that I love this little cup; it saves me money, it saves the environment, and she has crippling cramps that send her home from work and curled up into a ball on the floor so I figured she could at least try it. She just won't listen because the thought of a cup inside you is disgusting (but a little stick of cotton associated with TSS that so many people forget to remove [something her mom actually did for a month and got very lucky] is perfectly fine). Other friends tend to just brush me off as if I'm a whack job or that I'm kidding around when I say they should try it.
I've also been thinking about trying it with my mom, but she just went and bought some 250 pads when a department store closed, and I don't think she likes the thought of me inserting anything in myself. She's a very typical Asian mother who's highly conservative and lives by tradition. If they didn't do it where she came from in rural China, chances are she wouldn't even bat an eyelash to think of doing it today.
I know others have some great success stories in converting others to cups. I wish I could bring some friends over too! :)