How To Break Up Your Friend’s Awful Relationship

Marjan Apostolovic / (
Marjan Apostolovic / (

We’ve all been there: One of your friends is dating someone who is quite simply the worst, and you just don’t understand what they see in this other person. (I believe the parlance is either “pussywhipped” or “dickmatized.”) In these situations, a couple’s friends sort themselves out into two types. The first type doesn’t want to get involved, assumes their friends are adults who can make their own decisions, and keep their mouths shut no matter what. The second type have perhaps watched too many episodes of Intervention but realize that when things get severe a good person will at least make an attempt to say something—and will let the matter drop if rebuffed.

Both sides have something to recommend them, and both have pitfalls in their application. In the first case one can be guilty of being a fair-weather friend, more interested in preserving a friendship than in actually looking out for someone that they supposedly care about. The second case smacks of miserable busybodies who want everyone else to be just as miserable (or as single) as they are. In neither of those situations do most of us have the objective perspective to be certain that we’re doing the right thing instead of acting viscerally. It’s a tricky thing to ponder.

I’m of the mindset that one should give one’s friends every possible benefit of the doubt. Yes, it’s true that relationships can be traps where one or both people lose their sense of self. But they can also be pockets of greatness that outsiders simply don’t or can’t understand—and even if they could, it would be none of their business anyway. Even bad relationships can have very many positive consequences, both as cautionary tales or even merely the benefit of having companionship for a period of time.

I found myself in this outsider’s perspective with regard to one of my closest friends, Toby. He and I had known one another since high school. During the decades since we’d never had even a minor argument. We complement each other well, and over the years each of us learned a great deal from one another due to our disparate interests. He’s kind of a jerk masquerading as a nice guy, whereas I’m kind of a nice guy masquerading as a jerk.

I liked Isabelle when Toby first started dating her. She had a great appreciation for humor, was very intelligent, and knew how to have a conversation without being annoying. Yes, she had her flaws—but I didn’t have to deal with them, and everyone has flaws to put up with. Most importantly, she made Toby happy.

At first.

About six months after they started dating, Isabelle moved back to Arizona to complete her schooling. Toby decided to go ahead with a long-distance relationship, with him flying to Phoenix or her returning to New York every so often. Things began to be a bit more difficult, but that is inevitably the case with an LDR. I felt my role was to listen to him vent as a means of relieving stress and thereby keeping the relationship going.

But as one year turned into two, I started noticing red flags. Isabelle was in the process of getting her doctorate and had never had a job. I’m not sure if that contributed to their drama, but it sure didn’t help. The crux of the matter was that she had a Disney-princess view of relationships. She felt her boyfriend’s role was there to validate (she called it “support”) whatever decision she made about anything. Even when she was doing the wrong thing by her own admission, his job was to be encouraging because she felt “bad enough already.” This was the case even when she did the wrong thing again. And again. And again. He was never to criticize but always to be her cheerleader.

Still, I held my tongue.

Things finally came to a head when marriage talk began. Isabelle was a devout vegan, and she unilaterally declared that any kids they had would be raised vegan. They’d even be getting their start on whatever the vegan equivalent of milk is, because she didn’t want to breastfeed. There was to be no discussion; her veganism was very important to her. I thought this was insane, but the particulars weren’t what bothered me. What bothered me was her approach.

What makes or breaks relationships—and I mean any relationship—is whether there are mechanisms in place for resolving disputes. Can the people involved argue without it becoming irrevocably ugly? Are they committed to resolving things once tempers calm down? Will they give the other person a hearing to state their case without punishing them for it? And in this case the answer was no.

The kid wasn’t even born and Isabelle was already issuing decrees without the slightest pretense of caring about Toby’s view. What would happen when the choice of schooling came up? Or any of the other difficulties that come with parenting? Buying a house? Without a space for Toby to make himself heard, this was going to get worse and worse for him over the years. In my view, he was going to ruin his life if he married this woman.

Toby was also starting to realize things weren’t all they were cracked up to be. But Isabelle treated any complaints on his part as illegitimate, as attacks, or as illegitimate attacks. She’d accuse him of imaginary things which “must” have been what was really driving his discontent. Toby began to simply hold his tongue. There was no point in causing trouble if nothing changed and it only caused drama.

I wanted to say something, but at the same time he would be able to tell me—correctly—that I didn’t understand the situation. I also didn’t want to interfere unduly, nor did I want him to resent me for butting in. I wanted to give him perspective, not orders. Isabelle was giving him enough orders already. Then I came upon a great idea that would do all these things without any of the negative consequences, and I’ve found that it’s a technique that works for any bad relationship. I took one of the IMs between the two of them—and I animated it.

Now, instead of rereading the text and “autocorrecting” to make excuses for Isabelle, Toby was forced to hear the dialogue as read by speech generators. He had no choice but to listen to it with cold, hard objectivity. That’s what it took for him to finally understand that he was dealing with someone who wasn’t exactly “the one.”

The site I used,, is now defunct. But there are plenty of alternatives. It works on couples, or for people in bad job situations, or for those who are generally being treated poorly. The best part is that you aren’t sticking your nose where it doesn’t belong and offering your opinion. You’re simply quoting someone else verbatim and letting their own words damn them. Thought Catalog Logo Mark

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