I’ve been very skeptical and expressed this suspicion to him, but he keeps defending her. What the fuck.
Most Helpful Guy
The online thing is a concern, the fact that they have never met. He needs to be careful.
The age thing is ok. I mean at the end of the day we are all just flesh and blood and life is so short that you just need to do what makes you happy in this regard.
You don't know what is going on in his head. I know it sounds unusual but he may be craving a strong female role model or someone who is a bit of a protector in a sense. Also, the more you question him the more you will push him towards her. If you want to help then just keep an eye on things from a distance and only intervene when something dangerous is happening.
Most Helpful Girl
He may be your close friend, but there is nothing more that you can do.
You've already provided your concerns and opinions. All you can do, is be there to support him and be someone he can continue to talk to about this stuff so you can ensure safety. This lady does seem to have concerning behavior if she is acting like a jealous teen... BUT all you can do is ask him to be safe and make sure he knows all the safety numbers, date rape drugs, etc.