As long as your mates don't decide at 2am, whilst well oiled, that you should all go to the strip club. Or worse still, decide to go after you have gone home!
Mate, you just have to go for it, if it works out it sounds like you will end up with a very attractive woman who is switched on. If it doesn't work you can look back and say "I went out with a stripper once". Doesn't every red blooded male want to have done something similar to that in their life?
I have spent my fair share of cash (and some others shares!) on strippers and enjoyed every minute, they are a great set of girls and when you hit it off you can have alot of fun, just a good laugh. I found it really makes a massive difference if you can be confident, not always easy when your with your mates with all these fit half naked girls around!
My wife was a dancer in night clubs back in the rave days of the 90's and although clothed at all times there was always a certain type of reaction from people when you would say she was a dancer, then you felt you had to explain what type of dancer as people would chose to have an image/opinion straight away. She also had a degree and became a school teacher in the late 90's, the dancing was for fun.
So, not the same as a stripper but some situations will be similar. We have been together for 14 years and have two children and everything in life is great. So just go with the flow, see how it pans out, don't spend too much time thinking about it or what anyone else might be thinking. And have fun!!