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How (and why) to Root for Team Awkward

JanFirst2011 asks:

I am 15 years old and I have only made out once. I do not know the person I made out with, and I don't exactly remember what it was like. I want to make out with more people, but I am afraid I will not be good at it, I also don't want to embarrass myself with the person I do make out with. Another thing is, what if the person I do make out with tries to do more with me than I am ready? What should I do and how do you recommend getting over these fears of mine? Thank you!

Do I need to prove my love to him by giving him money?

Jasmine asks:

So basically I have this boyfriend who is 2 years older than me. The sex is great and everything is fine. He really is one of the sweetest guys I have ever known. We have been together for months. I went out with his best friend first (who I lost my virginity to). He is perfectly fine with that as it was 2 years ago. Just one minor flaw. I was also under a lot of pressure at the time I lost my virginity and so when he asked me for large amounts of money, I gave in, believing that he loved me. It would not be an understatement to say that he ruined my life. He told EVERYONE at school what happened between us. However, he only told his friend (my boyfriend) about the money.

I am deeply in love with my boyfriend, and everybody is happy for me. When I say he is the most generous, kind guy I really mean it, and my caring friends also agree. But now he has asked me to give him money. Now I appreciate the fact that I am more well-off than him and his friend...but still. He said that if I love him I would give it.

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