There is this really cute guy but my family is really close to his, I have never been out with anyone before and I don't no what do, how do I find out more about him? How do I get him to know I am into him other than flirting? How can I see him often without making it obvious?

Just talk to him,ask him about his likes and dislikes. Do you attend the same school? You do not have to flirt with someone just to get to know them. At 14,there are so many other things to do and talk about. Forget about flirting and just be yourself.

We do not go to the same scool but we have cottages near by. I wouldn't say we were exactly frensds and he isn't very easy to get hold of. Plus he popular which makes it 10 times harder any advice?

I forgot to mention that I have never been out with anyone and have never been kissed

how do i get him to know i am into him other than flirting? how can i see him often without making it obvious?

I'm confused, do you want him to know you like him or not?
As far as the first part goes, just tell him. It doesn't matter if he is "popular" or not, or your dating experience.
Just ask him out.
A question never asked can always be assumed as a "NO"
And a "NO" is better than a "I wonder..."

If you think he's in to you, go over and tell him yourself. I was once fourteen, and I used to tell the people I had feelings for that I had feelings for them. Thius always worked for me. Best of luck.