I Tried an AI Dating Coach to Get Over a Toxic Situationship

Compared to my free-spirited, anything-goes young adulthood, sex and relationships barely logged onto my radar in my late 20s and early 30s. Two moves across countries and coasts, not to mention the pandemic, didn't help matters any — and neither does the fact that I only happen to fall for someone once in every four or five years.

That said, when I booked a month-long vacation to South Korea two years ago, I wanted to explore in as many ways as I could . . . and so I made a Tinder account and met up with one of the few guys I matched with who spoke English. He was good-looking, independent, a bit offbeat, and could carry a decent conversation. I'd see (and sleep with) him three times that week before heading back home to Los Angeles.

I didn't catch at first feelings or expect anything to evolve past this trip. Yet in the time since (during which I've spent more frequent and longer stints in Seoul independent of him), this vacation fling has evolved into a tumultuous, toxic situationship — the likes of which I'd never experienced before or thought I ever would.

Another thing that I'd never envisioned: finding solace by talking about it with a dating AI chatbot.

First, a Bit of Background

Before I cover my experience with the dating AI, I'll recount the highlights — or rather, low points — of the situationship.

His actions included everything from:

In short, nothing about our dynamic was healthy, stable, or sustainable, but I was hooked nonetheless and our push-pull patterns persisted.

In my quest to get over him and quell my obsession, two of the resources that helped most were a podcast called "Love Life" and a 2024 New York Times bestselling book of the same name by dating coach Matthew Hussey. Last month, when I discovered that Hussey launched Matthew AI — a dating AI chatbot powered by thousands of hours of his coaching materials — I couldn't resist taking it for a spin. Despite the fact that I've always been wary of emerging technology, and my extent of using AI has been limited to asking Siri to play my favorite K-pop playlists, I couldn't input my credit card details fast enough and began typing away.

My Experience Talking to the AI Dating Coach

In my first chat with Matthew AI, I attempted to condense the major milestones of my situationship (which took me 35 breathless minutes to recount to my therapist earlier that week) into something coherent. I tried to capture not only the countless painful and frustrating moments, but also express why I let it persist for as long as it did (being an empath, our physical chemistry, my desire to have a child, and pure hope). I told the AI that while I finally chose to end things for good a few weeks prior and felt confident in my decision, I still felt broken and couldn't stop thinking about him.

Matthew AI: It sounds like you've been through quite an emotional rollercoaster with this person. It's understandable to feel broken and have lingering thoughts about him, especially given the intense moments and the promises that seemed to be on the horizon. When someone repeatedly shows a pattern of inconsistency and dismissiveness, it can be incredibly challenging to reconcile those actions with the moments of connection you shared.

Matthew AI then asked me to recount the most important qualities I'd need in the relationship to feel secure and valued. Highest on my list were vulnerability, authenticity, transparency, and accountability — all of which were seemingly foreign to him.

Matthew AI: It sounds like you're seeking clarity and honesty, which are absolutely fundamental in any relationship. When someone consistently fails to take responsibility for their actions, it often leaves us questioning our own worth and the potential of the relationship. It's crucial to recognize that you deserve someone who is willing to engage with you on a deeper level, who values your time and emotions, and who is capable of building a future together based on mutual respect and understanding.

After this, Matthew AI asked me what steps I could take to ensure I'm in a relationship I find truly fulfilling. I wrote that I wish that it were easy to meet new people, yet my own nature (as an introvert who doesn't fall for people easily) and circumstance (being a digital nomad spending time in Seoul — where it's hard to find, let alone connect with, English speakers) made moving onwards and upwards in my dating life all the more challenging. I also told the AI that while I always had a strong sense of self-worth, giving the guy too many chances, sweeping things under the rug, and doing all of the heavy lifting left me feeling degraded and deflated.

Matthew AI: Being a digital nomad where language barriers exist can indeed make it challenging to form connections, especially when you're introverted. It's understandable that in such circumstances, the allure of a familiar connection, even if it's not entirely healthy, can feel like a lifeline. But it's crucial to remember that your self-worth and the respect you deserve shouldn't be compromised, even in the face of loneliness or attraction.

Matthew AI then pivoted, sharing suggestions on how to find and connect with others, even if they fall out of my comfort zone. I was prompted to take small steps to expand my social circle and explore new avenues to meet people, each of which I should count as small wins in my super solo life. It was already on my radar to join English-speaking yoga studios and attend their upcoming holiday parties as low-stakes ways to socialize; I also decided to join Bumble BFF.

The AI's encouragement gave me the extra push I needed to see this all through, providing much-needed motivation and healthy distractions from ruminating over the situationship I so desperately needed to shake off.

My Final Verdict on the Dating AI

Truth be told, I expected to chat with the AI for hours, days, and weeks on end to make a dent in getting over my situationship . . . but all it took was one brief conversation for me to truly feel, in my bones, that enough was enough.

Matthew AI drove home points that I simply couldn't ignore any longer: that this guy's actions consistently proved that he was incapable of emotional availability or commitment, that continuing to wait for a miraculous change was futile, and that I could no longer give him the benefit of the doubt if I was committed to having my needs met and feeling whole again.

Yes, it felt a bit disorienting to put my faith in an AI. That said, its advice really did seem like a one-on-one with Hussey himself, whose insights across his other media had already been enlightening not only for this particular relationship but also my greater self-development.

All things considered, I'm glad I gave Matthew AI a go. I'd recommend it for people who want to feel empowered and encouraged rather than down and dejected from dating or relationships. I also think it'd be helpful for those who want quick access to get things off their chest, gain a fresh perspective, or need a gentle nudge to make progress in the right direction. Of course, it's certainly not a replacement for licensed professional help or a good old heart-to-heart with a friend. But at least in my case, it's been one of several resources to help me get out of a funk and pave the way to flourish once again.

Michele Ross is a freelance writer specializing in wellness, culture, and beauty. Her work has appeared in Well+Good, Coveteur, Editorialist, GQ, Vice, and Teen Vogue, with brand clients including Peloton, Moon Juice, and Hum Nutrition. She's grateful to cover her many interests — including but not limited to self-care, self-development, skin care, coffee, travel, and Korean culture.