What a sensitive topic. My daughters are very young so I'm not faced with that as a mother, but I was a teenager that did all the wrong things...so I feel like I know something about that part.
I don't believe there is any one way to handle any teenager because every person is different. But here are a few things I learned looking back at my own experience with my mother and father.
1.) Try not to be hurt when your teenager starts to be a little more to themselves. It is natural to be shy about topics you know your mother might disapprove of. And as a mother how do you get across your views on such things and still have them tell you when they are feeling differently. My mom talked to me when I was about 13...she knew I was becoming interested in boys. She told me that if I ever thought about having sex I should talk to her about it so we could discuss maybe getting on the pill or talk about the boy in question....but then she ends the conversation with..."well I know you will wait until you are married." So I knew that I should never go to her and talk about it.
2.) I know that you are trying to give her room to breath and be independent but at 14 I think (from experience) that time unsupervised with friends is asking for trouble. I think unsupervised teens get into way more trouble than their parents want to admit. Even innocent trips to the mall are just invitations to do what they will. So you say when do I trust them. You do trust them but you have to realize that teenagers don't have the ability to reason....for the most part most will not be able to make an adult decision when put under pressure. I just read a big study where they studied the brain patterns of a teenager and discovered that the area of the brain that is responsible for reason and decision making is very undeveloped until the age of 19 to 20. Most kids can't make consistent responsible choices when put under pressure and unsupervised.
I know many will disagree with me, but I don't think they are honestly remembering their own teen years or even willing to admit that some of their behaviors were destructive. Most want to think that they survived and that makes it okay. I survived too, but not before I suffered physically, emotionally in some pretty horrible ways. I'm an adult now and over it, but I shouldn't have experienced what I did and it was because I was given freedom. I was a straight A student, I did chores, I helped with my brothers, I cleaned house, I cooked dinner, I had friends, I was nice and polite......but I had low self-esteem and would do anything to be accepted. I could say the right things to my mom and dad. I would repeat what I knew was the responsible responses...but what I did behind their backs was totally different. Because it is different when you are talking to your parents or an adult and you are pressured by a boy you really like to have sex. Or asked by a really cool friend if you want to smoke a joint. Put in an unsupervised situation where all your peers are doing things and looking at you most will do what they know they shouldn't because they can't stand the thought of being ridiculed or rejected. And that is the truth that everyone wants to deny.
3.) At that age I think most teens think their parents are out of touch. They believe that parents make a big deal out of everything. They will listen to their friends way more than their own parents. Don't be insulted or think you have failed. It is natural. I taught middle school for nine years. You don't know how many moms I talked to that believed their little girl always told them everything. They beleived their little girl never lied to them. They believed that their little girl was responsible and would never do anything stupid because they had a talk. There wasn't one year I taught that at least one good little girl didn't end up pregnant. That was in middle school. A recent Reader's Digest article said that 65% of highschool kids today are sexually active. I do believe their numbers are super low. I didn't know a single virgen in my graduating class...and several of my fellow classmates were walking the aisle pregnant. That was over 20 years ago...It is worse now.
I've often wondered why is that? I think we give our kids way to much freedom now. We want to be our kids friends instead of their parents. We are so afraid they will hate us or feel like outcasts if we impose rules that other kids don't have. We allow our kids to watch soap operas where it's cool to jump in and out of bed with whomever we please. Then we wonder why they take sex so lightly. We let them listen to music that glorifies sex before marriage and then we wonder. We let them pal around kids that we know are making poor decisions and then we wonder why our kids did some of the same things. We let our kids run around unsupervised at the mall, in the neighborhood, and at other's homes we don't know and then wonder why they got into trouble.
My first sexual experience at 14 was behind a movie theatre where my parents had dropped me off and then picked me up. My first drug use experience was at a girls house that they knew was a bad influence but they didn't want to hear me cry and tell them that they didn't trust me. The first time I got drunk was next door. My parents knew that they were not responsible parents, but they let me hang out over there anyway...because I cried and accused them of not trusting me.
I could have been a lawyer. Oh how well I laid out the reasons they could trust me. I made straight A's, I respected them, I was involved in school activities, I was inducted into honor societies, I always followed their rules....
My parents told me I couldn't date until I was 16. My mother relented when I was 14 because I cried and complained for weeks. Then they would pick us up and drop us off at the movies for weeks. They had no idea what was going on. I was a good kid...but I wanted to be loved by a boy. It was important to have a boyfriend. There was something wrong with you if you weren't dating someone.
My parents didn't have a clue until I was 17 and by then it was way too late. I always said the right things, made the good grades...most of the time I even had the nicest friends.
Too much freedom not enough reasoning brain power. It is a fact kids will often make the poorest decisions if they think they can avoid being caught.
I wonder how many kids out there will actually call their parents when they have been drinking? How many will decide to wait until marriage? How many will not experiment with drugs?
I worked with middle school children and high schoolers after school. I have three aunts that teach in different states. We all saw the same things. Parents pressured by their kids to relent.
I don't know what you can do for sure. What will work? You know your daughter best. But please remember that she is at an age where she will probably be more secretive and she's probably under a lot of pressure by her peers and this guy she likes. That weighs very heavily on a teens mind and they don't believe that parents will understand.
I would continue to talk to her constantly. Even when she rolls her eyes or turns her back. It is getting in there. And please consider limiting any time away unsupervised. Always try to make sure your daughter is in situations with supervision by adults that are like minded.
You can't watch every moment, but you can be vigilent in most cases. And isn't because you don't trust her. It is because you know the facts and you know the reality of teens. Society today give way to much credit to teens. Yes they are smart. Yes they are active in social programs. Yes they care about the world. But they are still teens subject to peer pressure and still feeling this uncontrollable urge to be accepted that they can't even explain.
Hope I didn't offend you in anyway. Just telling you what I've learned from real life experience. Just some things to think about.