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Multiple leases for one dwelling..?

Rented out a two bedroom unit to a young woman who moved in with a roommate. Her name was on the written lease, but his was not (though I ran a credit check on both of them.)  She moved out with 3 months left on her lease and arranged for someone to reside in her room, which I allowed. When her written lease expired, the new person approached me asking for a new year-long written lease in his name, and I agreed, presuming the arrangement with the other guy would continue.  It turns out that the guy who lived there for the full year wanted to arrange a lease with me and live there alone, and he's quite upset. Additionally, guy #2 with the new lease wants guy #1 out so he can move in a friend instead.   I don't want to be the bad guy here, and the truth is that guy #1 was a great tenant who caused no problems and always paid rent on time, but guy #2 came to me first regarding a written lease. I'm not sure how to handle the situation, because I don't want guy #1 to be forced out.

So my question is - can I have two separate written leases for two different occupants, thus protecting both guys from being forced out by the other?
sounds like a huge mess just waiting to explode.  if you already wrote-up and signed with guy #2, done deal.  if not, there is no way to keep all parties happy. If they are not willing ro share the house, tell them to flip a coin or draw cards, something random. it would be a shame to loose a good tennent. do you have another property he might be interested in?
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