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Two people on probation could live together with the permission of the probation officers. Usually they do not allow it because of the "bad influence" factor. There is usually a better chance of getting the okay for this if the people knew each other beforehand. In other words, meeting in jail or at the PO's office is not considered to be a good prediction of success. Also, I have found that if the two people both have drug problems or drinking problems, it is less likely to be approved.
I hope this helps.