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I'm not sure I can be much help, but I do have a 16 year old daughter also. I have had to deal with a somewhat similar situation. My suggestion ( if you haven't already done this) is that you sit down and have a serious talk with her about this. I would explain to her that even IF this boy and her are just friends she needs to cut ties with him. She knows he has a girlfriend, she knows the girlfriend doesn't want this friendship to exist. She needs to respect the girlfriend's wishes, and not be friends with him. It's up to the boy to decide if he wants a girlfriend that puts these restrictions on him. What if the shoe was on the other foot? Say your daughter was in a relationship with this boy, and he was text messaging another girl saying "Hey beautiful" and spending a lot of time with the other girl. I doubt she would like that. Your daughter is looking at this friendship only from her point of view and what she gets out of it. It is clear that this guy is attracted to her. He tried to pull some moves on her before. Those feelings usually don't go away. My question to your daughter would be, " Why don't you become friends with BOTH of them?" Afterall, it's just a friendship. I'm quessing your daughter would not like the idea, but it is a way to get the girlfriend to be okay with the friendship.
There is nothing wrong with being friends with the opposite sex. But when it is against the wishes of the girlfriend, boyfriend, spouse, whatever, that's crossing the line. No friendship is worth lying, sneeking, making excuses. Unless it is more than a friendship.
Also, I would make it clear that you will never cover-up the friendship for her. Tell her if she continues the friendship with the boy , you will not keep quiet about it. The friendship could eventually get back to the girlfriend. When you see this boy, ask him how his girlfriend is doing, how long have they been going out, why don't you two double-date, etc. Talk about other boys your daughter likes in front of him. Let him know in some many words, that you know he's playing her, that he can't get his cake and eat it too. He has no right to be jealous of your daughter seeing or talking to other boys. You need to call him on this bull****. Your daughter may hate you for doing this, but as a mom you cannot stand by and watch her be manipulated by an 18 year old boy.

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