How far should I go on this first hang out session?

A female age 30-35, *rs07k writes:

I'm recently single from a 5 year relationship with a guy I planned on marrying. I'm 20 years old. I met this guy that is the brother of one of my friends. He's really nice and sweet and we've hung out twice since I met him in a group. Well, on Friday we're going out and smoking hookah. I'm not sure if other people are going to be there or if it's a date but I'm going to assume other people (aka his friends) will be. I've never dated anyone besides my ex bf and I don't know what to do, how to act, what to wear...I basically know nothing. I've met other guys since I've been in college on a brief stint when my bf and I broke up for a 3 month period last year and I wasn't successful in meeting guys. But I feel like this one might be different and I don't want to mess it up. I would genuinely like to see if things could work out between us. I think guys tend to get turned off by girls that go too far. I already made out with him when we went out once...we were dancing and we ended up kissing for a while. So now, I'm not sure where we stand or what he expects but I know he's very into sex. How far should I go on this first hang out session? And what do I do if he wants more? Any help or advice would be greatly appreciated...especially before Friday night. Thanks everyone!!!!

View related questions: broke up, kissing, my ex, period

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A male reader, cupids_friend  +, writes (26 February 2009):

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A female reader, Louise89  +, writes (26 February 2009):

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