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Your main issue, which is the root cause of your problems-school, body image, relationships- is your lack of confidence. Wherever your poor self-esteem stems from, it has NOTHING to with who you actually are. Some of the smartest, most talented people end up struggling in life due to low confidence. Low self-esteem can affect anyone, regardless of how beautiful, smart, talented, etc., one is. On the flip side, some people who are not what most would consider "attractive," overweight, not exceptionally smart, are confident and secure enough with themselves, and have less issues than people who "have it all." My guess is that half the issues you have faced in the past are made worse by your low self-esteem. You were in the top five of your class, and though you've been struggling with your studies lately, you are clearly one smart woman. Re-enrolling at a university is not easy, and you not only did that, you achieved something most can only dream of doing. So good for you!
Trust me, I know what it is to feel like shit, for no reason other than a lack of self-confidence. Although I have grown a lot and am much more secure and confident now, I have really struggled with not feeling good enough. I used to think I was so shy, practically incapable of making new friends. I used to keep to myself a lot. I also used to think that I wasn't "pretty," like all the other girls. This is the past- I am now 26, and though I know I have a lot more to go (I could be more assertive, and stand up for myself more- two lessons I have learned the hard way this year), I have grown a lot, through my experiences and mistakes. The truth is, we all have our insecurities, but at some point, in order to really live life, we have to learn to develop thick skins and be happy with ourselves- regardless of the mistakes we make, what we look like, etc.- after all, we are all human. Being "perfect" is an imperfection. Making mistakes is a part of life- they make you learn and grow.
As for your relationship- I can relate. I tend to be attracted to men who are unattainable: the guy who I find good-looking, but who also happens to be with a girl, the guy who is probably "out of my league" (but maybe not actually "out of my league" in reality). I have never gone out with a guy who is attached to someone else-I refuse to. But I do find myself sometimes falling for guys who have a girl. I have thought about it, and came to the realization, that I don't necessarily want THAT guy, I just want what his girl has: a relationship. Maybe I'm so unhappy with being perpetually single (I value my independence, but have been single for a long time), not having had a happy, long-term relationship (my longest "relationship" has only lasted a few months), that I see something I want and fall for it. Not hard. But I see girls on the train with their boyfriends-they seem happy, and i want what they have-not because I'm jealous of them, in particular, but because I long for a relationship (which is to say, some sort of emotional connection with a guy).
The problem is not that this guy is younger than you. It's not even the main issue that he is already in a relationship. The problem is that you think you "feel things [you] shouldn't feel." There is nothing that you "shouldn't" feel, when you have an intense connection with someone. You regret feeling these things, because you do not want this relationship to go "there." You should not get involved with this guy, at least not now,-not because he's younger, but because he's already attached. But be honest with yourself. Could you see yourself with him? Does he make you feel happy and "yourself," so much that you could actually see yourself in a committed relationship somewhere down the line? If you see him as a friend, and nothing more, then still continue that friendship, and try not to look too deeply into things.
Remember, the only person you have to answer back to is yourself. If you feel like crap about who you are, what you look like, what you haven't achieved, then the only one you are REALLY hurting, is yourself. Relationships, school, body image, etc., these things are only negatively impacting you, because you are letting them get to you. Trust me, I have a ways to go, when it comes to being totally self-assured and confident; many of use do. If you think you could use someone to talk to, keep counseling/therapy as an option. Sometimes our biggest weakness is denying, rather than confronting our problems. Even a school counselor can listen to your concerns, and help you sort things out for yourself. I am in grad school now, and have dealt with all sorts of family/relationship/classmate issues, and i only wish I had talked to a counselor when I really needed someone to talk to. The path toward greater self-awareness and confidence is really f**king hard, but nothing worth fighting for is ever easy.
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