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To make a long story short, my daughter has been dating since the age of 15 1/2, mostly in our livingroom. She will be a senior in High school next year. Her beau is nearly 20 and a fine Christian young man. They see each other about every other day, and on Saturdays, spend almost all day together. We have never had any problems with this relationship.

We have a 14 year old son who has been in love with this girl for 3 years. He has gone thru major emotions about her during this time. Two weeks ago, her boyfriend broke up with her. My son was there to pick up the pieces, and now he is on top of the world! She is a very nice girl! I am so proud for him!

We have had a few issues with him in the last couple of years.
Found a magazine under his bed, empty pack of cigarettes, got caught cheating in class and has had problems with his language. He has always been very sorry and has seemingly changed and been repentant. He has gone thru thinking that he is just going to turn out bad no matter how hard he tries.

The girls best friend is one of our neighbors.
My son went over and spent 4 hours with her Tuesday night, with plenty supervision. Thursday night she came over to our house and spent 3 hours. Tonite, our son went to a birthday party with her and then to her house, with her mom there. I told him that we would be picking him up in 3 hours. We did.

The problem: He is so mad at us he acts like he could kill us!
He wanted to stay for another couple hours and watch a movie. We stuck to our guns and picked him up. He says the reason he has so much problem with worldy activities is because we have sheltered him to much. I really don't feel that this is true.

The question: What kind of parameters should we set for our 14 year old son? What do we do when he compares his sister's freedom to his? I need help!

The problem: He is so mad at us he acts like he could kill us!
He wanted to stay for another couple hours and watch a movie. We stuck to our guns and picked him up. He says the reason he has so much problem with worldy activities is because we have sheltered him to much. I really don't feel that this is true.

The question: What kind of parameters should we set for our 14 year old son? What do we do when he compares his sister's freedom to his? I need help!

Hello Reggie  :)

I would like to say regardless of the ground rules you have for your teens,  one of the most important things to remember is say what your mean, and mean what you say (hopefully parents will apply that at a very early age)  Trying to make you feel guilty for the rules you set is not an unusual tactic to try to get more leeway, but something I learned that is very effective in handling that is to say "if you complain about the rules, you get more rules, if you complain I grounded you for a week, you will get two weeks, if you complain you have to be home at 10, next time i`ll make it 9..."  no complaints in this house lol
You asked about perimeters, and my thoughts on that are a parent cannot go wrong in knowing where their teens are, at all times, knowing who they are with,  when to expect them home, if they object to our being 'overprotective' they have the option of staying home.  Children are all different, and as Butcha said, when you feel they are ready for more freedom you give it, really that goes by how well they handle the freedom they already have, or do they use their freedom to break the ground rules.  With freedom comes responsiblity, if a child is not mature enough to handle the responsibility, then the freedom should be taken away until they have proven they are ready.  
I have yet to see any negative effects from our being strict, rather our children 21/16/15  seem contented to know what we expect of them, and they also know what they can expect from us...tho my youngest boy sighs now and then and says "if mama aint happy aint nobody happy" LOL    ;)

I agree with the advice given so far.

I'm pretty new to the forum, and just noticed this fairly old thread. I'd like to add that teenagers need structure and limits, but many Christian parents make a major mistake by stopping there.

The key to helping a teenager grow in responsibility and in the Lord is through your relationship with him or her. Spend time talking. Listen. Encourage. Do things together. Otherwise, being strict is liable to backfire. Think of God. He clearly presents us with structure and linits, yet they are part of a powerful, loving relationship. When you talk, "Do not let any unwholesome talk come out of your mouths, but only what is helpful for building others up according to their needs, that it may benefit those who listen. (Eph. 4:29)"