When I was in HS there was a young man with special needs who had been urged at some point to ask girls to "be his girlfriend". He'd talk about kissing etc. all the time. People thought it was funny and girls agreed to be his "girlfriend" so he'd get a big smile, a hug and walk away. I was uncomfortable with it and did not play along as I could see a situation such as the one described in the OP, in which he would act inappropriately, not know or understand it was inappropriate and perhaps become upset when the women of the world didn't play to his rules.
As for volunteers wheeling people out to pickup, my son had a surgery this week and a bright, chatty girl wheeled him out with us. She talked to him in an engaging manner (it was the first time in his little life that he strung two words together) and then she returned the wagon so we didn't have to. It was a great service IMO, but I can see how easily someone could choose to gain access somewhere they aren't needed and become an annoyance, too.