Have you ever let your significant other try to put your cup in for you? Would you ever consider such a thing? Would you be mortified? Would they? Do you think a man (or a woman even) could get it in the right place if you talked him through it? Could your partner identify your cervix?
This is theoretical, but I had a boyfriend one time who was so curious about how tampons worked that I let him do it for me one time, but cups could be different. This can be an extremely private matter for some women and not a big deal to others. What do you think?