My DH has been on one guys trip and that was for 2 days to go to a football game in Denver. They always talk about going, and try to plan one, but nothing ever happens.
He does however play golf whenever he wants and meets up with friends for drinks. He's a huge homebody and hates not being in his own bed, so I guess that's good for me.
As far as being o.k. with him going, it would depend on who he was with, where they were going and how much it was going to cost us
I do have girls night about once a month and I love them!! I always tell him to take advantage of mine and go out with his friends. Most of the time he just stays at home and uses it as his alone time.