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I have another question or two.
How possible is it for you to join him with his friends now and then? Not every night or every time they go out because that would be smothering to him if that's not what he wants. If he won't include you at all that would raise a red flag for me.
Also How long and how late is he out with these friends? Is he out to all hours of the night? He will need to be responsible to you some because of your close relationship. Do you live together? and Does he tell you where he's going or when you can expect him home? That is a simple common courtesy - I'm not saying to drill him about every detail just to say that - should an emergency happen or he gets hurt even then you can know something is wrong or needed when he doesn't return 3 hours after his intended time.
Last but not least - What is he doing with these friends? Bowling? playing cards? or Drinking and partying? Does he come home innebriated or high on something? That is a warning sign that he's got some issues that need working out.
I agree with those above who suggest taking time to make sure you have friends and your own little support group to get through WHATEVER comes of this relationship. Take time to make sure you are in good health and cultivate your own happiness. Then whatever happens won't hurt you as much and if you can work things out you both will be happier.
Hubby and I are happiest when we both have a little bit of freedom and outlets of our own besides things we do together. It's a delicate balance but it can be achieved with cooperation and communication. Wish the best. Hugs
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"Always learn the rules so that you can break them properly." Dalai Lama
My Karma just ran over your Dogma. 
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