I would tour with my GF on several occasions and enjoyed it a lot. Alas, she tried it and it never really took. (At most she will do supported events.)

Outside of that, I don't think I would tour with anyone, much less a stranger I met on the Interwebs. My first tour was Adventure Cycling's unsupported Northern Tier group tour. Twelve people and a leader. Let's just say that there were a few people I could have seriously done without. And there were instances when being able to have more autonomy would have been nice. I also enjoy my alone time. I am not one of those people who needs to socialize a lot. My next two tours were each over a month long and both were solo, with one being in a foreign country. I am comfortable with my own company so I didn't mind being on my own.