Simply the fact that you are considering breaking up with your boyfriend for Bob is enough reason to end the current relationship. However, I wouldn't rush into anything serious with Bob until you spend some time together platonically and make sure these feelings are real, not just a leftover crush from when you liked him before. You should spend some time by yourself to sort out the complicated feelings you are having and tell your boyfriend that you care about him, but that you need some time alone, which will be true if you don't get involved with Bob right away. If you are patient and take your time with Bob, you'll feel better about the situation in the long run because you won't have guilt from cheating on someone. Of course, your boyfriend will be hurt, but he would be more hurt if he new you were leaving him for Bob. At this point, you are not obligated to tell him everything. If things don't work out with Bob and you end up wanting to get back with your boyfriend, then you will need to tell him what happened while you were apart. Jumping from boyfriend to boyfriend, especially with overlap (meaning you start dating the new one before ending it with the old one), is not conducive to a healthy emotional state. If you become too used to constantly having a romantic companion, you forget how to be single, which makes breaking up with men even harder because you are afraid of being alone.

I had a very similar situation as a teenager. My dad kept moving in with different women and hauling me around from relationship to relationship. I got really sick of always having to change schools, not to mention get used to living with people who weren't really my family. But I just made the best of it: focused on my studies, took advantage of whatever clubs and organizations the school offered, and formed new friendships through common interests. I learned that when you are a kid, you have little control over what happens to you, but you do have control on how you let it affect you. Eventually, you will graduate from high school, attend college or get a job, and move out on your own, at which point you will be able to have a relationship with your father that isn't dependent on his love life, but is a pure bond between the two of you, free of resentment or anger. Who knows? You might be able to start giving him advice about life one day.

You probably miss your friend and it hurts to think about her, but you should try to remember the fun times you had together without dwelling on them. Friends are wonderful people to have in your life, especially when you have a lot in common and hang out all the time, but you have to spend time alone as well. Though your friend may have had a huge influence in shaping who you are now, you must take that experience and continue to move forward on your own. You have to learn not to depend on others for your self-worth. Once you are confident in who you are and truly like yourself (i.e. become your own best friend), you will attract other like-minded individuals. Everyone grows and changes throughout their entire lives, no one ever stays the same, and real friends understand and allow each other to do so without making them feel guilty, even if it means going in a new direction and leaving friends you care about. You'll meet hundreds of people throughout your life who will have some kind of impact on you, so it's almost impossible to keep in touch with them all. The only person you'll always have is yourself. Some people find this philosophy depressing or cynical, but I find it liberating.

Sex is a natural and wonderful experience. I waited until I was 19, but that was only because I couldn't find someone I cared about and trusted until then. If you have found that person, I say, go for it! And remember, the more you practice, the better you get, as long as you always use protection. STDs and babies = no fun.

I have much advice to give you as I have probably tried everything at least once. I've studied human behavior for years by immersing myself in various environments and participating in different rituals. Sometimes this involves morally questionable activities, but I feel the need to understand the way the deviant mind works as well as that of more cooperative members of society. After analyzing my experiences, I've come to the conclusion that our reactions and interactions are all basically the same at the core. No matter the situation, I should be able to dig up some first-hand wisdom for you.

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