Relationship advice: Should you step in when your friend makes a mistake?

The sad truth about being a grown-up is that most of us aren’t really ready to be one, which means long after you think you’ve seen your friends through the worst of their adolescent missteps, you’ll find yourself seeing them through some mistakes that are bigger than kissing your mutual friend’s ex-boyfriend after his football game. Note to my 16-year-old self: who cares?!

Do you have a friend who is about to marry a total d-bag? A friend who is thinking of getting pregnant with a d-bag’s baby? A friend who got pregnant with a d-bag’s baby and put pictures from a naked pregnancy photo shoot on the Internet? Maybe one friend who did all three? Well, here are some things to help you get through massive mistakes that aren’t your own.

How close are you?
Is this woman one of your ride or die chicks, or just a girl you kind of know. The former means you need to read the rest of these questions. The latter means you need to mind your own business.

Is telling her how you feel going to make her life better?
Or, more importantly, is not telling her going to make her life worse? Yes, there is a difference. Trying to make her life better (or ease the potential consequences of her actions) is different from trying to make yourself feel like a better friend.

Is this mistake ruining your friendship?
Really. Is the mistake she’s making going to change the very fiber of your friendship, or is it just annoying you? Is what she is doing (or about to do) so colossal that you just can’t live with it as her friend?

Do you have a plan?
Because these conversations don’t just lean toward the awkward, but easily veer into the aggressive. Treat this like any serious business conversation: be confident. Know your bullet points. And don’t be drunk.

Have you ever spoken up and it back-fired on you?