Is it okay if I pretend I'm selling something on craigslist to get two strangers to meet awkwardly?
Why would you want to make two strangers meet each other?
I want people to communicate in person
You are being dishonest with people and wasting their time. You need to behave in a more responsible, adult way. This behavior is not entertaining, it is mean.
I'm going to do it anyway and maybe someone will enjoy it.
I don't think anyone will enjoy having their day wasted. Now if you want to give them something for free or offer to sell them something at a discount, then maybe they wouldn't mind meeting.