Can I ask why you're giving an ADULT gas money and paying for his insurance? If he can't earn the money, he should walk to school. Same with the phone, that's not a need in any way. You don't say why you don't like his girlfriend, but honestly, I would say get over it. He is an adult and is allowed to make his own friends regardless of your opinion. I know it sounds harsh, but you've had 18 years to mold him into who he is now. Trust that you've done everything you could. I would start trying to befriend her, invite her over to dinner with your family. And calling her to complain about your son? That's so out of line regardless of age. This is between you and your son, not her. Give him the space he needs to flourish and become an adult. You need to transition yourself from overly-protective/controlling mother to support and friend.