I am reposting from some of my favorite dating sites.

Doctor NerdLove, I was hoping that you could possibly help me with a very difficult situation I’m in.

The girl I’ve been interested in for the past month, who is also quite a good friend of mine, has a boyfriend who is by no means a decent human being. The other day I discovered that he’s cheated on her a few times and I’ve decided that as a friend it’s my responsibility to tell her. I’m not sure if that’s the right decision, though, and I’m not sure HOW to tell her at all. If you could please weigh in on this, I’d seriously appreciate it! Thank you so much.

Waiting In The Wings

Well, you asked, but I don’t think you’re going to like my answer.

Here’s what you do, WitW: you back the hell off.

First of all, let’s be honest here, just you, me and the Internet: you’re not doing this out of the goodness of your heart. You didn’t decide that it’s your responsibility to tell her because you are that good of a friend, you’re hoping that when you tell her she’s going to dump her cheating scumbag of a boyfriend and fly into your arms as the one who helped her see the truth. Which, to be perfectly frank, is a pretty shitty reason to deliberately insert yourself into the middle of somebody else’s relationship drama.

But for the sake of argument, let’s game this out a little. Let’s assume that either I give you my blessing to telling your crush about her supposedly philandering beau or you decided to go and tell her regardless. How, exactly, do you think she’s going to react? Here’s a hint: she’s going to take it badly. Under the best of circumstances, she’s going to be pissed off like nobody’s business. The only question is who she’s going to be pissed at.

And the smart money says it’s going to be you. You may have noticed that people don’t appreciate bad news. In fact, we tend to get irrationally angry at the person who brings us the bad news, whether it’s their fault or not; there’s a reason why “don’t shoot the messenger” is a common phrase, after all. So you’re already starting off with your would-be hunny-bunny ticked off that you’re telling her that something’s rotten in Denmark.

But then there’s the next step: why should she believe you? Do you have proof? Do you have unquestionable proof that you can actually show her? Proof that couldn’t possibly be explained away? Because if you don’t, then it’s going to be your word against her boyfriend’s. And sure, her boyfriend may be an assbag, but he’s still her boyfriend. This gives him more credibility in her eyes than you have… especially if either of them know that you’ve got a crush on her. And believe me, if she doesn’t, he almost certainly does. This is going to be leveraged against you – you’re going to look like you’re lying up in order to break them up.

(And let’s be honest: that’s what you’re hoping for here.)

Now let’s add another wrinkle into the mix: what makes you so sure she doesn’t know already? Right now you’re working from limited information – you know he’s cheated on her. You don’t say you know when it happened, whether she found out before, whether he confessed or she confronted him and whether they’ve worked through it or not. For that matter, for all you may know, they may have an arrangement of one sort or another. So you’re going forward and telling her with the distinct possibility of re-opening old wounds, dredging up past problems or stumbling onto the fact that they were only socially monogamous. None of which is going to work out for you the way you’re hoping.

Let’s throw a third wrinkle: how’d you find out? Did you catch him in the act? Did you prowl through his phone or emails? Or did you hear it from the grapevine? Because she’s going to want to know… and she’s going to want to know why, exactly you were prying into her business. All of this is going to make a difference, because it’s going to be demonstrating your agenda rather strongly. And if you two aren’t honest-to-god BFFs – which, from the sounds of things, you’re not – it’s going to look like you went digging for dirt, even if we grant that your motivations were as pure as the driven snow. And that is going to bring you right back to that credibility problem.

But hey: let’s say that you manage to thread all those needles and she dumps her no good, scummy boyfriend. Assuming she doesn’t lash out at you for causing her break-up, she’s still not going to swoon into your arms. She’s going to be pissed off at men in general and in no mood for your trying to be the next in line… in fact, she’s probably going to resent it. Women don’t appreciate it when guys suddenly assume the window of opportunity is open because they’ve literally just broken up with somebody. She’s going to need some time to recover and your hanging around in order to help her through this ordeal is going to start verging rather seriously into Nice Guy territory.

In short: you’ve got yourself your basic no-win scenario. And you’re not going to Kobayashi Maru your way through this.

This isn’t your business. Your getting involved is only going to add another layer of drama to somebody else’s relationship. And even under the best of circumstances, it’s going to end badly for you.

Leave it alone.

Photo credit.