"My friend just got engaged to someone I think he should break up with. All the times I’ve hung out with them, this guy’s given me the creeps. I think he’s weird and not very nice and a total step backwards for him.  I never said anything about it to him when they were just dating. But now that it’s so serious, I feel like I HAVE to do something. How do I bring this up to him? If this goes badly and they have to divorce, I would feel terrible to have just stood by and let it happen."

Cause if you just stood by and let it happen, then you wouldn’t be able to say "I told you so," right? And where’s the fun in that? Not being able to rub someone’s terrible breakup in their face and point out your amazing ability to tell people what’s best for them?

All right, let me take a step back and apologize for the attitude. I just kind of had to get that out. For the rest of this column I promise to assume goodwill: that you just want to look out for this friend and feel you have an obligation to be honest even when it’s hard and endangers your friendship.

That’s a legit responsibility: to be brutally honest when you see loved one careening towards catastrophe. Like if your friend starts listening to juggalo music, even if for ironic reasons. "Friends don’t let friends" and all that, ya know.
So let’s sort through the situation.

WHAT KIND OF FRIEND ARE YOU?
Are you best friends with this dude? Are you likely the only person who will ever be able to see this impending disaster and be able to say something?

Or are you only an acquaintance, but you think you have a lot of personal experience that gives you license to dole out advice?
Be honest.  Sometimes, the ones with the strongest opinions are usually the ones with the least information.  Here’s a quick test: if this guy didn’t call/email you for two weeks, would that be a big deal? If not, you may not know as much as you think you do.

WHAT ARE YOUR MOTIVATIONS?
I know, I know, you only want the best for him. But why do you care? Is it because you think he could be with someone better?…. Maybe you?

Is this situation reminiscent of one you’ve experienced and you want him to dodge the bullet you already took? Is it because it’s easier to help out his relationship situation than your own? Is the fiance ruining the dynamic in your friend group or are you the only one that has a problem with him?

WHAT IS YOUR EVIDENCE?
And by evidence, I don’t just mean evidence this guy’s bad news, but evidence that your friend will listen to you. Has he asked for your opinion? Has he said, "I’m not sure about him" or "I don’t really want to get married, but…." Or exhibited worrisome behavior? Did this engagement come on the heels of a tragedy in his life? Does it seem like he had no choice in the matter?
And really- is he really BAD for your friend or just not good enough? If he’s abusive, lying, unfaithful or otherwise  endangering him, that’s an entirely different matter from just being not good enough for someone you hold in high esteem. You need to figure these things out before you go to him or the conversation is just going to devolve into chaos and anything helpful you might have to say will be completely lost in the ensuing argument.

WHAT DO YOU WANT TO HAPPEN?
So let’s say the conversation goes exactly as you’d like: you warn him, he takes it seriously and then…… what?
Breaking off an engagement is an entirely separate species from the regular ole "it’s not you, it’s me" kind of dating breakup. It’s awfully hard to just step back. You have to give them credit as rational beings that they thought through this huge commitment.
Do you want them to postpone a wedding that is coming too quickly and take things slower? Or do you want Flavor of the Week put on the next bus out of town, to never be heard from again? You might affect both of their lives forever. Do you need that kind of responsibility?

NOW WHAT?
So think all these things over and then, if you’ve determined you know this friend well enough to be a helpful voice, have a calm, sober conversation between the two of you. Ask why he is getting married, ask him why he’s marrying him, ask him what he hopes to get from marriage to him. If any red flags go up, address them specifically.
But if he responds with love, devotion and well-reasoned commitment, you need to be ready to step the fuck back and keep your opinions to yourself.

This is a hard topic. Sometimes it’s only because of true, trusted, insightful friend that we get the guts to get out of bad relationships. And for those people, we ought to be grateful. Just make sure you’re one of them.
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