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People with issues and problems like that like to be around other people with the same, this way they feel "normal."
IMO, this guy is going to have to deal with a lot of excess baggage, including a rather large loan that will quickly become HIS responsibility.
2 years is not enough time to really know someone, this is about the time that people change into who they really are. I'd tell him to let them date for another year and have her get her finances and life in order. People surround themselves with people who they want to be--losers with losers and winners with winners. I'd tell him that she needs to slowly pull away from these people that are bringing her down and find new positive friends.
/dr phil
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