New years resolution: do the one thing I thought I'd never do

Siiiiiiiiiigh. Ok, so just thinking and writing about this makes me extremely nervous. So, I'm not really out at all to anyone. Technically I told a professor my freshman year in college that I was bi in an informal essay, but that's only half true and he's old so he probably doesn't remember anyway lol. Pretty much everyone I've ever personally known has suspected or asked if I'm gay, I just haven't had the guts to actually confirm it to them. I mean, I'm just sitting here thinking about it and I can't even count the times I've had to straight up lie to people about it. I should have told my ex-girlfriend three years ago, but I made up the excuse that I didn't want to have any kids when we got married (which I knew we weren't going to ever get married), and she had wanted at least 3 kids, so long story short, we soon broke up. I really liked her in a romantic way and all, but I could not for the life of me tell her my deeper feelings, or lack thereof. It sucks really, because I pride myself on being an honest person with most things. It's just that I have to come out on my own terms to people and I'm afraid telling one person would create a snowball effect, you know? What's more is that most of the people I interact with on a daily basis (friends, parents, co-workers, teammates) are very religious and/or conservative so I just can't see myself coming out all at once to everyone. I don't know though. I want to believe it wouldn't be that bad if I came out, but I could see it ending up bad with some people I'm close to. But I want to try to turn this around in 2015. I'm tired of living a lie. Honesty is too valuable to give up for security and falsity. Cheesy or not, it's true.
So I've been best friends with a guy literally since we were babies. We went to preschool together, we've been to every birthday party together, we hang out together more than with anyone else (I've been browsing the forum and I can see that many of you can relate to this on some level.) And I want him to be the first person to come out to—I mean it's pretty much a no-brainer. Out of all my friends, he's probably the most relaxed about the LGBT community. He's even said he doesn't mind gay people before. The problem is not telling him; the problem is telling. You couldn't ask for a better friend to come out to...I'm just afraid I'm going to freeze up and end up not saying it (the huge issue I had with my ex-girlfriend.) And even though I can trust him, if I do tell him I'm worried it might get out to my other friends when I'm not ready for it. He's a lot like me in how we're slightly socially awkward, so I just hope it won't be a train wreck whenever the subject of the LGBT community comes up with my other friends who don't accept LGBT people.
I don't know, am I over-thinking this lol? It's something I never thought I would do, yet I'm so ready to do it. We're gonna hang out this Friday and I told him I needed to talk to him about something, so the ball has started rolling...it's just scaring the heck out of me to think about it. The feeling is like getting on your first big roller coaster and you don't know what's going to happen or how you're going to feel after the first big drop.
Anyway, if you've read this far, thank you. Reading and watching videos of coming out stories has really helped build up the courage. Obviously I don't have anybody to talk about this to, so thank you empty closets for providing the space to get this all out.

 

Thanks Wildside
I actually went through that same phase practically all throughout my teen years. Like I said, I had a girlfriend, so I was really trying to live the "normal" life. But that was only what others expected from me and not what I felt nor wanted for myself. I was also an eccentric person in school, so I got picked on a lot and people would question whether I was gay or not. Of course, I denied it every time and it just built up a huge wall of suppression over the years. And getting picked on for being assumed gay was bad enough, I really didn't want them to actually know I was gay. So I really tried to believe for a long time, like you, that I was straight, or at the least bi. Now that I'm in college and I've grown intellectually, I look back at those years and am embarrassed not because I was picked on, but for missing a lot of opportunities to be true to myself.

So anyway, I resolved my new year's resolution and came out to my best friend! It's such a relief and it really makes me appreciate how fortunate I am to be friends with him because he took it even better than I expected (and I had high hopes to begin with.) He didn't seem weirded out or anything and when we were talking more about it, it was just like any other normal conversation we've had before. I think it helped that we were walking in a nature area, where we go to often to catch up and see wildlife. So word of advice to any potential coming outers: definitely find a place both you and the other person are most comfortable with.
We also hung out with some of my other friends later that night, which is what I was most worried about. They made a lot of gay jokes as usual, some directed at me, but my reactions to it went as usual (putting on the same "straight" mask, but I'll come out to them when I'm ready eventually.) It's nice that the friend who now knows I'm gay is a pretty quiet and unassuming guy, so it's good to know I probably won't have to worry about any awkward situations when we're all hanging out.
But man, it just feels like I'm slightly opening the closet door and finally getting my first dose of fresh air. So relieved to get this first step out of the way!