1. What are appropriate boundaries for you? What topics are fair game to talk, when and for whom?
2. How do you decide which requests from your friends / family / coworkers to fulfill, and which ones to say no to? For example, if a friend is asking you to listen to their problems, what would you consider in deciding whether or not to listen right then?
3. Where did you get your idea of appropriate boundaries from?
4. What were boundaries like in your family? (I am asking this question because boundaries are defined very differently in each of the culture I'm part of).
1. My boundaries usually are centred around maintaining enough physical, emotional, financial, time and resources margin that I can still meet my own needs and have something left to give other people. The rule of thumb for me is that when people start to become disrespectful or want me to do something that endangers me and is not in my best interests, my behaviour towards them needs to change so that I am sending a clear verbal and non-verbal message that their behaviour is not appropriate and won't be tolerated.
Boundaries are often decided for me by how close I am to the person and what our relationship is. Some topics or information are off limits to some, when I would easily share the same information with others. I think it is important to give clear messages to people about what you are or aren't open to. Sometimes they throw out feelers into the conversation by introducing certain topics. You can choose to go with it, or to block the way, depending on where you want things to go. I think when people are behaving inappropriately it is important to do the opposite of what you would normally do to make a person feel welcomed, accepted and comfortable, or else you are giving them a tacit message that their behaviour is okay, because yours has not changed towards them.
I'm pretty open about most things within reason. I'd feel comfortable sharing a lot of experiences that some might see as being personal, as long as they were things I had processed and which I had learned from. I see invitations from the opposite sex to discuss sex as a way of them testing interest/openness and so avoid that because I don't want to give them the message that I'm interested in a casual sexual relationship. I don't appreciate people who are not in my inner circle referring to me by pet names or acting overly familiar or touchy. If people try to be overly cohearsive or persuasive about their points of view, without showing sensitivity to my responses, I am unlikely to open up to them and will probably behave much more coldly than I naturally would be inclined to.
2. Over time, I'm learning to promise less but be more scrupulous about keeping my word. By not being unreasonably accommodating, it forces people to decide whether or not their request is reasonable, it helps me to prioritize better (instead of just responding to the most demanding person), people feel more secure because they know they can rely on me and they better know what to expect, I get less resentful (and don't feel as taken for granted), people are more respectful of my time and resources and they are more thankful for what I do do for them.
Usually, I give people the benefit of the doubt at first. However, if it seems that constantly they require a lot of my resources, but are not willing to take advice or change their circumstances, I draw back a bit. I also have a few guidelines for myself about not lending anything that I could not do without getting back (my car, bigger amounts of money etc) and never co-signing for anyone, not going into business partnerships with friends or family, etc so that we can maintain our relationship.
Generally, the closer someone is to me though, the more leaway I give them as far as how far out of my way I will go for them. If they have had a history of investing in my life, I will go to great lengths for them. Their past behaviour also tends to serve as a guideline for how much priority they are given or what I will do for them.
3. My ideas about appropriate boundaries probably came in part from discussions with my mother and from her being willing to share a lot of real life stories about herself and other people that we knew. She was very good at being pleasant, but drawing appropriate boundaries around herself for others.
I learned from busking, where I had to script myself on what I would say in certain circumstances if asked to go somewhere with someone I didn't know, if I ran out of time for a person who wanted to keep talking, if I felt uncomfortable or in danger, if someone wanted to play my violin, if drunk people accosted me or wanted to shake hands and wouldn't let go or invaded my personal space, or if people asked for inappropriate information for how well I knew them.
Watching my parents try to help others and seeing that sometimes you learn as you go about where you should have drawn boundaries informed my views. Living in the north where people asked many unreasonable things of me and were sometimes very volatile, insecure or needy, but were not ready to change made me see the need to protect your margin and your resources enough that you are still able to be effective and contented.
Watching my extended family and siblings make choices in their lives taught me a lot about boundaries in relationships and about teaching others to respect and value you effectively. Teaching forces me not only to practice drawing appropriate boundaries everyday for my students, but also has made me think about how to teach them what kind of boundaries they need to draw and defend in their own lives. It made me think about a lot of situations where we as teachers and parents and family members can help kids by "scripting" some possible statements or behaviours when different situations come up that they may be surprised by or uncertain of how to react to in such a way that others don't take advantage of them.
Teaching private lessons taught me that it is better to be proactive and plan for the worst, while expecting the best from people. I learned over time to get people to pay at the beginning of the month, to value my time more (but also give more!), to explain my expectations more fully, to lend things out less, to require a bigger commitment from parents and to be less accommodating. As a result, I have students with more supportive families, I have less problems from a business standpoint and it is a much more pleasant experience all round. It took a number of years with occasionally getting burned by people I hadn't expected to behave in that way before I had the confidence, conviction and courage to do that.
My last relationship also taught me how some things can kind of sneak up on you over time, so you need a balanced life full of meaningful people and pursuits, other people's perspectives (who have a stake in your life going well), and an equal balance of power and responsibility between both people to maintain a healthy relationship. I learned that you both need to be able to provide for your person's needs and accept provision for your own. When either partner cannot do one of these, it throws the balance of power in the relationship out of whack and it also inhibits closeness and trust. Honesty and vulnerability is a big part of being able to get close to someone. These principles also extend to non-romantic relationships. If an adult relationship is to be a balanced one, both parties need to have something to offer each other and they also need to both be able to benefit from something the other person has (and acknowledge that). To maintain healthy boundaries, people need to choose appropriate candidates to invest in and be involved with who have something to offer and are able to receive what they have to give as well.
More often than not, things go awry when one person is doing most of the receiving, while accepting little or no responsibility. And yet they remain in an alpha position in the relationship. They cannot appreciate what is being given to them nor admit their need because they cannot trust, so must always look out for their own interests. Because of this preoccupation in getting their own needs taken care of, they are restless and do not feel responsible for giving care to the other person. They see themselves almost as a child, yet want to take the dominant role and are jealous of anyone or anything else in the other person's life that could compete for their affection or attention.
4. I think both of my parents were pretty easy-going and accommodating. At the same time, I think neither of them got walked all over by other people. Most times when they did get surprised by someone violating boundaries, the stakes were pretty low. Usually it happened as a result of a lack of experience with certain types of people. Once they were made aware of it, they learned from the experience, without becoming cynical. I think they were trusting and had a desire to help others, without being naive about it.
They tried to set them and I was always trying to cross them. After we all move out, we still liked each other, despite, or because of, those earlier altercations 
