Get personal: How to open up to your friends
Before you open your mouth, take a few minutes to think about how much you want to say about whatever is on your mind. If you feel comfortable enough to tell the whole story, then go ahead. But if you just want to make an announcement, or give a brief overview of what's been going on that you've been keeping under wraps, that's OK, too. Don't feel like you have to spill anything that makes you uncomfortable, just because that's what friends do. Do know, though, that talking about what's bothering you will likely make you feel better. Your bestie might not be able to fix the problem, but it helps to have someone to share the burden with.
How to bring it up
If you two are already talking about sensitive subjects, your big chance can come at any break in the conversation--just start talking. But if you're goofing off or doing something fun when you decide you want to open up, saying something along the lines of, "OK, this is really random, but I really need to tell you something," will set the tone and get your friend's attention. She'll be hanging on your every word, waiting to hear what it is you need to get off your chest.
If she asks why you didn't tell her something earlier, go with the truth. Perhaps you were embarrassed, perhaps you were scared, perhaps you just didn't grow up in a "sharing" household, so it didn't occur to you. Whatever it is, your bestie should understand where you're coming from...and she should be interested in helping you come out of your shell even further. A true best friend will always be there to listen and support you, no matter what you have to say. That's why they call 'em best friends for life, right?
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