Ask Dr. NerdLove: Do I Tell My Crush Her Boyfriend Is Cheating On Her?

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.

Hey Doc,

Got a question for you. I’m a lady who recently took the initiative and asked out a guy I had some chemistry with. We’re in the same fandom world, and finding nice and normal people among us is very rare. Being totally generic for the purposes of protecting identities, we became friends by mutually respecting what we’ve contributed to our fandom.

I started to reach out to him on email a few months ago. We had a few conversations, in which he threw in some comments seemed like bad attempts at flirting. Not everyone has game, right? But after initiating a few conversations, I decided to let him reach out to me, and he didn’t. OK. Fair enough. Moving on….

Then I reconnected him at a recent event, and he started reaching out to me with gusto – emails, pictures (clothed!), etc. He even admitted to basically stalking me on social media, though he doesn’t really have a social media presence himself.

So after a few weeks of email flirting, I decided to be a grown-ass woman and ask him out. I was bold and direct (and funny). What I got back was a long, rambling email where he admits to being in relationship with someone else, but he doesn’t want to lose what “we have.” I’ve never seen evidence of him having a significant other, and I’d be really pissed off if a boyfriend of mine was having this kind of relationship with another woman.

There have been a few short email exchanges since my rejection. He’s done all the reaching out – I suspect either to take my temperature to see if I’d still talk to him or checking in to make sure I haven’t sunk into a vast depression (trust me, I haven’t).

What is up with men and their hidden relationships? Maybe his rambling was a nice way to hide that he just wasn’t into me like that? Since I’ll run into this guy at upcoming fandom events, what do I do? Honestly, I feel totally embarrassed and humiliated. I kind of want to tell him to go to hell, but I don’t want to be the bitter bitch who hates him because he turned me down. I also want to avoid him, but that gets exhausting, too. Trust me, if I had any idea he had a long-term GF or would turn me down, there’s no way in hell I would have asked him out in the first place. What was he doing starting this kind of relationship with me in the first place? Do I bother to continue a friendship which he seems to want even though I know it will never be enough for me?


Thoroughly Confused

There are a lot of possibilities here TC. It’s possible he was stringing you along because he liked the flirty attention you were giving him. He might have had a crush on you and was enjoying the thrill of new relationship energy and the frisson of a mutual attraction from somebody besides his girlfriend. Or it’s entirely possible that after you reconnected, he decided you were cool and wanted to be friends. I can’t say for sure one way or another – after all, I wasn’t there, and without interviewing you both and reading the transcripts, it’s kind of hard to say whether he was flirting – you say his game seemed kind of weak – and if so, how much of it was just flirting because flirting is fun and how much of it was flirting with intent. All that being said: I don’t think he was leading you on, and I don’t think he was deliberately hiding the fact that he had a girlfriend. Considering that you’re running in similar circles – fandom tends to be a small world, after all – it’s entirely possible that he assumed you knew he was seeing someone. Why didn’t he bring her up when you were talking? Well, again: I haven’t seen the transcripts, but it’s possible that the topic just didn’t come up. I’ve had many, many conversations with my friends – men and women both – where we don’t talk about our significant others simply because there’s no call to. It’s possible – even advisable – to have a life outside your relationship after all.

I also am willing to bet that he had no idea you were into him. When you straight-up asked him out, he suddenly realized that you two weren’t on the same page and suddenly things got awkward. Or maybe he had a clue that you liked him but was willing to ignore it in hopes that you’d end up romantically interested in someone else and you wouldn’t have this nascent infatuation between the two of you.

Either way: shit done got weird. So now what?

Before I get into what to do about this, I want to address your question about what was he doing starting a relationship with you at all. Something to keep in mind is that guys tend to have more emotionally intimate friendships with women than they do with other men. It’s a lot easier for guys to open up to women than it is for other guys; no matter how much people may talk about bromances, being open and emotionally intimate with another dude is still seen as being unmanly. Even the term “bromance” carries the “ha ha, it’s kind of like you’re dating” pointed nudging and and not-quite joking, and guys can be uncomfortable with this. So, we often seek out intimacy from our female friends, who tend to be less judgmental and more accepting of emotional openness. If you look at it from one angle, yeah, it can kind of look like a romantic connection… but it’s more about fulfilling an emotional need than trying to start an amorous relationship or conduct an affair.

But all that aside, the immediate question is: what do you do now that this is all out there, flopping around on the table like an Awkward Turtle? Right now, you’re feeling humiliated and probably a little angry. And I don’t blame you: you put yourself out there, you got rejected and that shit sucks. Getting rejected literally hurts. Take some time to let the sting fade and the anger cool off. Once you’ve gotten past the immediate pain, you’re going to see that it’s not as bad as it seems. Liking a dude who doesn’t like you back the same way isn’t embarrassing. Getting turned down, while sucky, isn’t something to be ashamed of. All that happened is that you found out that the two of you weren’t compatible. In the end, there’s really no harm, no foul. It’s hard to see it now, but with time and perspective, this will end up being one of the things you look back on with amusement as one of the wackadoo parts of the dating game.

So where do you go from here? He clearly hopes to continue your friendship. As I’m always telling guys, one of the issues with being in the Friend Zone is that you’re choosing to stay there. You say that being friends isn’t going to be enough for you – fair enough, that’s a valid choice. Just don’t treat his wanting to be friends as though he’s offering you the booby-prize, or that being friends is a poor substitute for romance.

If you don’t want to be friends with him and you don’t want to spend the rest of your time avoiding him whenever you might be at the same event, then I suggest you be straight with him. Tell him that he’s a cool guy and you like him, but you were hoping for something more.Let him know that trying to be friends with him would to be painful for you and it’s not fair to either of you to try and continue things when you’re longing for something he isn’t able to offer you. And then you just let things drift apart. If you happen to run into each other at events, then be polite, say hi and just keep going. If things get awkward, then just acknowledge the awkwardness. It doesn’t have to be a teeth-grindingly uncomfortable situation unless you let it be.

Good luck.

This post was previously published on and is republished here with permission from the author.


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