This may be a little long but I desperately need some advice and can't really go to family or friends on this one. I'm 22 and I very inexperienced in relationships, I have never had a boyfriend. I grew up in a very strict family, wasn't allowed to date or really go out in high school other than to the movies or the mall so I had very few friends as well. I also lived at home for the first few years of my college career so things were more or less the same as high school. I've been told by several guys that I'm a pretty girl (I don't say this to be conceited in any way, usually it is accompanied by the "why don't you have a boyfriend" comment) and I have had guys hit on me before but I'm shy and my upbringing has me scared to date as my parents were not very accepting when my older sisters brought boys home.
However I finally moved out of my parent's house last year into an apartment closer to my school. Shortly after I moved out I met a guy at my on campus part time job, he's gorgeous and is in a fraternity and has a ton of friends, we hit it off and became friends. Long story short this guy asked me out after a few months working together and we went out a few times and had a nice time, he was really awesome and nice when we went out and I really started to fall for him. He then invited me to a party that he was having at his apartment. I really wanted to go to his party but my few friends from school had gone home for the summer and I really didn't have anyone to go with however I decided to go by myself. I'm not much of a drinker so I hung out with him for an hour or so and then told him I had to leave. He walked me to my car and then tried to kiss me for the first time which caught me off guard. I stopped him and the only thing I could say was "we're just friends". Due to my shyness and lack of experience this was all I could think to say at the time.
He was actually pretty nice about things although he looked upset. He continued to be nice to me at work then he went home out of state for few weeks over summer break. He called me from home and unfortunately I missed his call and my roommate didn't write down his phone number. Then when he came back to school I saw him in a bar and we started talking. Eventually he asked me if I still thought of him as a friend or even more like a brother and due to my complete social ineptitude I moronically said yes. He seemed kind of upset and over the next several months he didn't talk to me quite as much but then we started hanging out in a group setting outside of work, his friends and my roommates and I.
Then something really weird happened, one of my roommates told me she had a huge crush on him and she asked me to hook her up with him as she knew that I was friends with him. Problem with this is that I had kept my crush on him to myself so in the interest of being a good friend and roommate I told him that she liked him. He said that he wasn't really interested in her but I persisted so he agreed to go out with all of us to get to know her a little better. We all went out and all I can say is that I experienced extreme jealousy as I saw them hanging out together and talking. However things between them didn't progress very far and that was the end of it.
Now he and I have been hanging out again, we've spent some time just the two of us over the past few weeks. I've now known him for over a year and a half and I'm completely in love with him. The other day I asked him if he wanted to go out to a nightclub, just the two of us, and he said he would really enjoy this.
After we go out together I want to ask him to come back to my apartment (assuming I have the courage to do so, which I'm working on) and to stay over and then see where things go from there. I'm struggling with this but this is the guy I want to be with, I have no doubts. I think he really cares about me as well and I know for sure he is not dating anyone.
I'm looking for advice as far as is this the right way to move this relationship forward and is this too soon to become intimate (if it happens)? I'm concerned that because of the way I handled his advances in the past and how I tried setting him up with my roommate that he won't try anything for fear that I might reject him again. Also, we've never really discussed much about our pasts and when he has asked me about my upbringing or high school I've kind of dodged the subject or kept things really general. Should I tell him about my complete lack of a past now or should I wait? I do feel inadequate around him because he has a lot of friends and I've seen many girls hit on him whereas I few friends. I really want to be with him but this painful shyness is hard to overcome. I'm afraid that if I don't initiate things then I'll lose my chance with him.
Thank you for any advice, I'm sorry if this is too long or if I sound like a complete nerd/prude but I'm struggling with this a lot.