Given his history, I would not find a female roommate acceptable. He clearly has no self-control and one day, this will come back and bite you in the ass and you will wonder WHY you went along with this. If you truly are set on being in relationship with this douchebag, then you need to set firm, immovable guidelines. One of them would be not even coming close to it appearing that cheating is easier. It will be if this chick moves in. No, no, and no. And if he gives you grief about it, find a real man.
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Maybe the reason your friend has suggested you toy around with married women or maybe older women is to get experience with women and sexual experience?
Yes, how much money do you have???
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