Three months is often about how long the infatuation stage lasts. Now the masks are starting to slip and you are meeting the real versions of each other. From what you described, he might be a misogynist, or he might just be immature and callous in dealing with women in general. His attitude towards his mother looks like a bad sign. His friend sounds immature, too. When I was younger, I can remember feeling a bit resentful when one of my close friends was busy all the time with a new girlfriend, but these days I am just happy for my friends to find happiness, even if it means we don't have as much free time for each other. So I'm guessing that you and this guy have been spending a lot of time together and his friend resents it.
Keep an eye on the misogyny thing. Pay attention to how he treats women, both family and strangers. For example, if he tends to be rude toward waitresses when you are dining out together, that is an indication of how he might eventually treat you. As for the situation with the friend, it would be healthy for your relationship if you and this guy didn't spend too much time together. Let him go to sporting events with his pals, and you should take time to hang out with your own friends, too.
Good decisions come from experience. Experience comes from bad decisions.