I Dated Different Versions Of The Same Guy For Years. Here’s How I Stopped

If you were to ask me how I was doing, say, two years ago, I would’ve offered up some variation of: “I’m good!” 

And I was! I had just landed a fancy job at a glossy magazine in New York; I had a tight-knit group of close girlfriends; my Instagram highlights were (annoyingly) curated with snapshots of espresso martinis and corner bookstores. I felt fine — great, even. Sure, I could be an excessive worrier, ruminating on pointless thoughts and biting my nails down to the quick. But my anxiety felt manageable. And I certainly didn’t think it affected my relationships. In fact, I used to pride myself on being a carefree and go-with-the-flow partner.

Until, that is, I realised I’d been dating the same, awful-for-me guy — over and over again. 

Even when The Guy would change, his centre remained the same. He was flinchy and ambiguous, emotionally unavailable and distant, a real Mr. Big from Sex and the City type. Shape-shifting was a hallmark trait of The Guy. It would always start off the same: I would begin dating an outgoing charmer with big ideas (that were actually never more than empty suggestions); or a wildly creative artist (concerned with nothing but his next project); or an unemotional stoner (who’d rather sit inside and watch reruns of Mythbusters than be bothered). Eventually, though, each of these guys’ differences began to disappear, and they’d reveal the same old tendency to run hot and cold with their emotions, to disappear for hours or days right when I need them the most, and, worst of all, to come sneaking back into my life just as I start getting over them. They all just became The Guy. 

I might have kept dating The Guy forever. But two events helped me see the cycle I was in, and gave me a chance to break free. First, I ended up dating The Guy again, and the experience was so painful — and such an exact replica of my last several relationships — that I was finally able to step back and see the pattern, and realise that it wasn’t just The Guy, it was also me. 

What I realised was that every time I began seeing someone new, I’d pat myself on the back for being so resilient. This relationship was different, I’d think. I was secure, confident — excited to enjoy the early stages of dating and see how things unfolded. But before long, I’d become insecure and needy. I’d morph from my typically casual self to someone who was frantically typing please text me back  into my phone, until I inevitably started to hate who I’d become: The Girl. 

Once I began asking myself why I kept making the same slide from chill to clingy, I realised that it wasn’t because of something inherently wrong with me, but was instead because all these guys were treating me the same way. The promised dates never materialized. The communication always trailed off. They came to me for help when they were in crisis, and disappeared when I needed the same. And as they withdrew, I’d get sucked in. I’d become furious when I never saw the outgoing charmer’s plans come to fruition; I’d become fixated on why the low-key stoner would rather watch Netflix alone than spend time with me. 

But even though I was becoming the same type of person because I kept dating the same person, I still had a problem: I had no idea how to stop. 

Then, a glimmer of hope arrived, via a therapist — though not my own. 

At the time, I had a writing gig at a magazine, and I was asked to interview a therapist for a piece in their health and wellness vertical. I can’t remember what the article was about, but I’ll never forget the interview. 

The entire morning, I’d been spacey and distracted. I’d spent that day — and a few days before it — worrying about The Guy. He was going through a hard time, which meant he was super-present in my life. He constantly wanted someone to soothe and reassure him. And I was more than happy to be that person — even though the weight of his problems was slowly crushing me. 

Although I was only half-present, something the therapist said quickly caught my attention. In a jewel-toned top, with her hair pulled into a loose bun, a few strands escaping to frame her face, she described something called attachment styles, which she said refer to the way you relate to other people. Then she described the anxious/avoidant trap. “There’s a push/pull mechanism that keeps the relationship alive,” she said. When someone with an anxious attachment style dates someone with an avoidant one, she said, it tends to look like this: As the anxious partner draws closer, the avoidant one runs away. Eventually, the anxious person gives up — at which point the avoidant person, who craves intimacy, returns, leading to a short-lived reconciliation. Then, the same cycle starts back up again. It can feel like being stuck on a loop, or a merry-go-round, or any other cyclical hell you’d like to compare it to. And I was living it. 

Even if the partners do manage to break free, the therapist explained, anxious and avoidant people often seek each other out in relationships because they’re each what the other is used to. Anxious attachers expect partners to be emotionally unavailable, and avoidant attachers expect to feel smothered in relationships. The push-pull mechanism might feel awful, but it also feels familiar, and that can be hard to escape. 

As she spoke, something snapped into focus. The Guy was always around when he needed help. But when I needed the same, he would recoil. “I freaked out,” he’d say, after fleeing in the other direction at the slightest sight of real intimacy. And when he’d inevitably return, I’d forget how manipulative he could be. He could be kind, but cruel twice as often. He was emotionally distant and I was weak. So even though we were the textbook definition of an absolute shitstorm, we would always circle back to one another, just like me and all the other Guys before him. 

That night, after I got home from work, I feverishly typed into Google “HOW TO STOP ANXIOUS/AVOIDANT TRAP.” I sipped a glass of wine as I clicked through articles, intending to unlearn some bad interpersonal behaviours. 

I think I thought that I’d be able to do a little work on myself, and my relationship with The Guy would straighten out. But I quickly found that my path forward wouldn’t be so simple. Attachment styles run deep, and I needed more help than Google could provide. Enter: therapy (and not under the guise of a magazine interview either). A good therapist helped me see that I didn’t have to be tortured with The Guy — or any of his iterations — anymore. It took a lot for me to come to that realization and when I did, I removed him completely from my life. 

After separating myself from the dysfunction and chaos, I was able to work on my anxious attachment style. I could spot bad habits that affected all of my relationships — romantic, platonic, familial — such as needing control and personalizing the behaviour of others. I started practising reframing anxious thoughts with positive self-talk. (Instead of thinking, Why am I not good enough? when someone treated me poorly, I began asking myself, Do I find their behaviour attractive?) 

I’ve also learned to be strict about my boundaries. As a recovering Cool Girl, the idea of setting boundaries used to feel like The Rules to me. You know, The Rules — those outdated, sexist guidelines for how to snare a match: Don’t reveal too much too soon, always leave them wanting more, never sleep with anyone until after the third date (or is it the fifth?). Every time I assumed a caretaker role in my relationships, my close friends would tell me to focus my energy elsewhere. I’d roll my eyes, feeling like it was just another script to follow, or another strategic plan to keep someone around.

Now I know better: My aversion to boundaries wasn’t because I was carefree — it was because they often got in the way of my ability to immediately soothe my anxious attachment style. Responding to that text The Guy sent after ghosting me, or brushing off the times he didn’t follow through on a date, allowed me to momentarily escape my fear of being abandoned, a hallmark feature of the anxious attachment style. But it also kept me trapped in unhealthy relationships, and ultimately, I found that the short-term discomfort of maintaining my boundaries pays off in my long-term happiness. 

Now I know that no version of The Guy would ever be capable of giving me the level of reassurance, love, and security that I needed. But it took being completely single for me to truly learn that. It’s like when you fall during a jog; sometimes, it isn’t until you stop running that you even notice the pain. If I hadn’t given myself a chance to stop chasing, my judgement would still probably be clouded. 

Being single also allowed me to practice sticking to my boundaries in situations that felt lower-stakes than a romantic relationship, like in my friendships. When I noticed friction with a friend or when I met someone new, I’d ask myself: Does this person positively contribute to my life or does my effort go unappreciated? Do they bring me anxiety or do they bring me peace? By the time I began dating again, I was used to checking in with myself often. 

Ultimately, my goal is to meet someone with a secure attachment style — but in order to do that, I have to have a secure attachment style, too, so I don’t become The Girl. 

In the meantime, every time I listen to someone lamenting a lukewarm partner or a friend asks me to ghost-write her text message to her hot-and-cold boo, I want to give them a big gigantic hug — or maybe the number of that first therapist.