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Stay friends? Forget him? Date again? Will it work out? What do I do?

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    I have been best friends with this guy who is 1 grade ahead of me since my 7th grade year. He and and I were always play flirting with each other and everyone always said we should date… so my freshman year we decided to give it a shot. We lasted 7 months, November to May 2010-2011, we decided it wasn’t working because we both felt kinda awkward since we were best friends before that. We did remain friends and since then he has asked for my help with 1 other girl and things didn’t go so well. Yesterday we were hanging out and he hugged me which is normal… but then he hugged me again and again and each time they kept getting longer and he seemed more reluctant to let go, and I realized I didn’t really want him to either. Then my best friend/might as well be adopted sister asked him if he liked me and he said, “I used to date her. I loved her. Part of me will always like her, no matter what….” she then asked if he would date me again and he replied, “Of course, she’s sweet, funny, smart, beautiful, she’s perfect… but I don’t deserve her and it didn’t work out the first time anyways. 🙁 ” She told him that I still like him, which I do… But I don’t know if dating him again is the right decision. I don’t want to mess it up again because the first time it was mainly awkward because I didn’t know how to let him completely out of the “friend zone”… I do really like him and would love to give it another try but I am scared that if it doesn’t work out I will lose him completely… This coming school year he will be a Senior and will turn 19 in April, I will be a Junior and turn 17 in January. I think I honestly love him and it scares me to death because I dont want to do something wrong and lose him…. what should I do?

    Ask Oracle

    I am glad you asked this – the thing is you are unnecessarily delaying things, unknowingly. Your situation is simply this – you are already inside heaven, having a best time but still wondering is this heaven? have I reached? is this real?

    If you pay attention, this is nothing but a terrible human habit to doubt things, and make things complicated.

    You know this person for so many years, very comfortable around him and even like him. And the same applies to him. You have already reached a position where most people fail to reach. What else one could ask for?

    And really only people at your age can reach so easily because we adults keep making things difficult for ourselves, we think, argue and doubt so much that it squeezes out and even kills all Love and Joy. Sad but true.

    It would be wise if you remember that Love grows in innocence and awareness. You already are innocent but lack awareness.

    My suggestion would be start enjoying and stop worrying, have fun and let go of confusion. At the same time learn new skills so that you can really reach deeper levels of Love and they don’t teach these things at school. 🙂


    Hi Jaydyn;

    I understand exactly what you are saying. I was in a situation like this with my best friend in high school. We did date for a short while and it felt awkward and very complicated. The one thing we were afraid of diong was destroying or friendship. So we did decide to just stay as friends and things were much more relaxed and we were much happier.

    It is complicating when you do date your friends. The one thing it can compromise is your friendship. Especially if your friendship is tight with that person. You will always have those feelings for each other. That’s something that will never really go away.

     I do respect you for the fact you are thinking and not making impulsive decisions without weighing out all the pros and cons of your situation. A really good friend that you can rely on is really hard to come upon and they are treasured and cherished. Having a romantic relationship with your friend that doesn’t work out can be pretty chaotic and I’m very glad that hasn’t happened in your case.

    You are rediscovering and going through experimental stages right now in your life. You have far surpassed your childhood. Which means you are not innocent by no means. You are growing into a woman. Enjoy this experimental stage, hun! Meaning, take one step at a time. You seem like a very responsible young woman. Enjoy this period of your life because when you are grown into womanhood you tend to loose your sense of fun at times.

     Just take care of yourself. Do somethings you really enjoy doing. Get the most out of your schooling. This is a very pivitol time in your life. Respect yourself! Appreciate you! Love yourself! Love you, for being you!

    Blessings to you! I pray that the angels guide and protect you at this most important time in your life! 🙂

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