Help? (mixture or topics so I just posted here)

Now that I've gotten rid of the problem of me not knowing and the problem with a friend now what do I do? Besides me only 3 other people I know ( and you guys ) know about this.I don't plan on telling anyone else about this anytime soon but when I do I want backup.I have sooo many questions to ask so I'm just gonna list them.
-When I do decided to come out Is it a good idea to tell my family that of my friends, my friends mom, and the internet know I'm gay but you don't?
-Is being around them going to be odd to my other friends that don't know?
Another story:
Their is a 17 year old that attends my online school and lives quite close to me. He said he has been gay since he was 14 and has no other friends at the moment. I got his number and have been talking and face timing with him for a few hours and I like him but don't know if he likes me.
-How would I know if he liked me?
I almost felt like just asking him but with knowledge of how last time went I probably won't ask him for a few days-weeks or wait until he asks me.
-Should I date someone older?
I know its not uncommon or anything because my mom and dad are 10 years apart but they didn't meat until she was 20.
-Am I ready for a relationship or should I be waiting and just stick with close friends?
My best friend Maddie and I have been together forever and It had gotten to the point were I am holding her and cuddling with her and making it look like we are a couple when we are not. We have only kissed 1 time and I really think she liked it but I didn't and the rest of our friends think we are still dating from that day.
-Do I keep acting like we are dating around our friends or do I make up some kind of truthful lie like tell them I asked her out because I was excited then later we thought I would not work because we were friends for soooo long and did not want to ruin that?

ANY other tips tip you guys and gals here have to help me would be amazing even if they didn't answer the questions I have here.They just might answer a few I didn't think about asking or didn't ask. Thanks! :help:

 

Maddie tells me that she does not care what other people think her, me, or us, and that me being happy makes her happy too but the way she acts I know she does care no matter what she says. I love her a lot but my feelings are stronger for men than for women. There are so many things in my had I can't put in words but wish I could.

 

Ok well I just gave in in front of my friends today. Some were shocked and the others acted like they knew. It was so easy since I already had Maddie on my side in case one of them went homophobic and went to look for meds, but none of them did! They we all supportive and told me they are glad I'm happy. And all the time before then I thought I didn't have any friends. I also stopped worrying about trying to get him(the 17 year old) to like me. He has no muscles and is white like a ghost so I just told him he is not the kind of guy I would really like so I'm back on Cameron...he is so masculine but gentle but I can't have him. grrrrrrrr. So I'm just going to have to deal with a poster of Tyler Hoechlin with no shirt for a while. This dude is my fave everything. My fave man, actor, shirtless, muscles. This erotic text I'm proud to share!