In terms of getting them out and not regretting it later, writing/journalling is what comes to mind.

In terms of whether or not to tell someone, maybe before saying anything ask yourself, "24 hours from now, how will I feel about having told this person what I'm about to tell them?" If you don't think you'll feel good about it 24 hours from now, don't tell them.

And in vino veritas, but also embarrassment. Don't talk about anything too personal when drinking with someone.