A parent talked with me recently wondering how to deal with her teen who will not take no for an answer, not the first time, not the second time, or the hundredth time. Somewhere along the line, maybe way before his teenage years, this kid got an inkling that if he just kept at it, there would be a crack in the ice. Maybe it starts with a "NO", then moves to a "we'll see", and then to a "if I see an improvement in your.... we'll talk about it". Even though in your head it is still a NO, you hope that by leaving the door a little open, your kid will leave you alone. Kind of like when you used to put your young child to bed, and you left the bedroom door open a crack. It made him/her feel less frightened of the dark and sleep, and gave them the illusion that you were still "open" and available to them.
Teens are extremely motivated to push as hard as they can to get what they want. Perhaps you have that teen who as a younger child was precocious and verbal, "your little lawyer". You may have unknowingly reinforced this "spirited negotiator"because you were so impressed by their creative use of language and persuasion. This child learns early on to impress his parents with this prowess, believes in his/her power of persistence, and in the end is able to achieve the goal, whatever it might be. When they were younger, these negotiations may have been about TV or video game time, or desire for a new toy or game, or wanting to stay up later, fairly innocuous requests. Unfortunately the request line now is for permission to go to parties/sleepovers at potentially unsupervised homes, or purchasing new technology toys whose benefits are only additional distraction from tasks they already avoid like the plague like homework and responsibilities, or wanting to go to a concert at a venue 50 miles from home that doesn't start until 9 PM, etc etc etc. Your teens persistence in the present is predicated on what has worked for them in the past. Enter "pit bull".
Here are two options. First, if this is an unequivocal no, no its not safe, no its not practical, no... Then here is your "I get it" moment: simply state the reason, say the "no", and say "I get you are disappointed, I know you are angry with us, but this time our answer will not change. I know you will keep trying to convince us differently, and that will piss us off, but we are not changing our mind." Now here is the really hard part, you need to be extremely consistent with this message without re-engaging with the pit bull since this only energizes and enrages them. When your teen follows you around the house, or texts you multiple times within an hour after you have left the house, and continues to be a royal pain in the a##, you need to literally walk away, shrug your shoulders, put on your ipod earbuds, do whatever you need to do to not re-engage in the verbal volleyball that will absolutely commence. Your teen is going to see a new side of you, the you that won't be deterred from a decision that you feel absolute about. This takes time and practice! You will find this hard. Your teen will be mad at you, and that is hard, but like all things in life, this too shall pass as soon as a new request arises that you will be able to say yes to.
For those requests for which you feel ambivalent, and may initially give a knee jerk NO answer. This might help. Your teen is an expert in hearing your ambivalence, and knows that this NO doesn't necessarily mean NO. So rather than giving a knee jerk NO, take a moment and follow these steps:
Step 1: Say to your teen: "I feel ambivalent about this, what do you think worries me about this?" Give them the opportunity to think this through for you.
Step 2: Say to your teen: "Yes those things do concern/worry me, what can you do to make me feel OK about them?" Make them have to come up with a plan that might help you make a decision.
Step 3: Say to your teen: "What will the consequence be if you do not follow through?" Perhaps at this point you may be able to say yes with the plan in place, or maybe even after you have heard their plan it is a NO. (then follow previous plan above) Hopefully your teen has done some good work here and you will support giving them a shot at showing you their ability to take responsibility for following through. After all, this is what you are preparing them for. All the life decisions where there are pros and cons. Helping them to figure out how to weigh out actions and consequences, so that when you are not around and need to ask themselves for permission, they will know what to do!