Hi, I have a problem and I was wondering if I could get peoples’ honest opinions about it, because honestly, I am utterly horrible with relationships and feelings, and I figured there are likely people out there with more experience and relationship smarts than me. I honestly feel kind of stupid for going somewhere for advice because I’ve always been the kind of person to keep my problems to myself, but this has been going on for about a year and I guess I’m just tired of not knowing what to do.
So, anyway, here goes. My best friend and I go way back – we’ve known each other since before we went into elementary school. But, in this last year or so, I’ve been starting to finally realize that I’ve been starting to like her as more than friends. At first I ignored it, for many reasons; first of all, there’s the whole problem of not knowing how she’d react if I told her, and not wanting to lose her as a friend. She’s my best friend, I kind don’t know what I’d do if I lost her, you know? Then, there was the fact that she was dating someone who doesn’t deserve her. They’d broken up once before, back then. Recently, they’ve broken up over him talking with another girl (among other issues they’d been having, that was the main thing she talked to me about), and gotten back together once more.
Both times they’d broken up, I considered telling her how I feel, but first of all I was too much of a coward, of course, and second, she’d dated him a long time, and she was struggling to get past it. What kind of person would I be to just dump more on her like that? I’d only make things harder on her, and honestly, that would just be selfish of me. I know she isn’t happy with him, she told me she feels trapped and is only in the relationship because she feels stuck. He’s becoming more pushy and possessive since they got back together. I’ve tried many ways to get her to realize he isn’t right for her, but there’s a point where I have to stop before I make her upset over it. After all, it’s her life and her decision. In the end, I don’t care if we get together or not – I just want her to be happy.
But, on the other hand, I feel that if we were in a relationship, she would be happy, because first and foremost I respect her and want nothing but the absolute best for her. I guess, after all this ranting, I’m just wondering if you guys think it would be best to tell her the truth or to keep it to myself? And, if I do tell her, how do you think I should go about it? I know for certain I want to tell her in person, but I also thought of giving her a heartfelt note with a gift, or even possibly just kissing her (but that would lead to WAY more harm than good). Thanks for reading my giant spiel, and sorry about the cliché love story.
LemonVibe 
I know TL;dr, but as someone who was an invisible nice guy and after some painful lessons and a personality shift I now have a beautiful wife and kids. I want to save you from years of misery and frustration.
If she liked you as more than a friend there would be signs. Since you profess to be clueless here is a list of some you should look for: triplew mantelligence dot com/how-to-tell-if-a-girl-likes-you/
QUIT FANTASIZING YOU’LL MAKE HER HAPPY AND WILL BE THE PERFECT BOYFRIEND. You don’t know that because people who match on paper (or in one person’s mind) doesn’t always work in real life. Even if it’s “clean” the more you fantasize the more out of reality you will be and your true friendship will eventually suffer.
Instead get your #%$ together. If you are not super hot, super funny, super rich, or super talented then your best asset will be being justifiably confident in yourself. You don’t need to have everything figured out but at least know what your good at, be working a good realistic plan, and know what you think is fun without acting like a doormat to whatever girl you’re dating.
You will not be everyone’s cup of tea but to some girls you’ll be catnip. Whether it’s this girl or the next you’ll be happier, more confident, and living a much better life.
I have been in the same situation but I was the girl and I screwed everything when he told me and now we don’t even talk anymore however we try but it’s so awkward between us now first you should know what she feels about you otherwise just tell her but if she say no then just forget don’t tell her over and over again that’s what happened with me good luck
Okay here’s what you need to do. Take her to her favorite place. Once you sit her down, look her straight in the eyes, and tell her you need to talk. You need to live in the moment, tell her how you feel she is in an unhealthy relationship. A TOXIC relationship. That’s actually a thing look it up. How this guy she keeps dating, is not GOOD ENOUGH for her. Tell her how you care so much for her. If you would actually take a bullet for her, tell her. Tell her that she needs actions not words. Once you lay it on her. Tell her that you have known her for so long, and you’ve been with her through so much, tell her that you would like to hopefully take this friendship to the next level. You need to show her that you care for her and you could make her so much happier. Tell her if you could you would give her the world. If she’s like most girls, then she’ll love it. Most of us love that sappy, corny stuff. Probably because it’s so hard to get from a guy now. Hopefully this helps. That was a really cute story by the way. Good luck.