Essay

What It’s Like to Date a Serial Cheater

Jake seemed too good to be true. He was.

By Haley Shapley Illustrations by Peter Ryan December 17, 2024 Published in the Spring 2025 issue of Seattle Met

This story begins, like so many modern tales of love and horror, on Tinder. Jake (not his real name) and I matched on Halloween.

He was patient while I spent a few weeks traveling, popping back up on the app periodically to ask me out. “No luck on Tinder in my absence?!” I wondered.

“Hahaha. Negative ghost rider,” he responded. “I’ve been on a Tinder hiatus lately. Coincidentally around the same time you left. Weird.”

We talked and laughed easily over Home Alone–themed drinks at the Sitting Room in Queen Anne. He’d just moved from Portland and said this was his first date since arriving in Seattle. He’d spent the past several years focused on becoming a firefighter and had moved around a lot for seasonal work. He was finally ready to plant some roots—and ideally find a long-term relationship.

That first date lasted three hours, an eternity for me. “I know you don’t like to be driven home on a first date,” he told me, “but can I at least walk you to the bus stop?” He gave a little wave as the bus pulled away, and on the inside, I was melting.

Before I met Jake, all my past boyfriends had been in my circle for at least two years before we began dating. I’d long resisted joining dating apps, mostly because it takes me a while to get to know someone. I wasn’t really sure I could meet a stranger and then want to potentially embark on a relationship with them.

But Jake was the ideal amount of vulnerable without overdisclosing. So many men had shown up to a first date either to tell me absolutely nothing about themselves or to rehash their failed engagements and share the dating profiles of their exes. Jake threaded the needle perfectly, slowly sprinkling in details across our dates—the time he was carjacked at gunpoint, the Fourth of July he spent on duty when he saw a dad die after a freak accident at a parade, the beloved aunt he lost in early adulthood, the breakup that changed his career path.

On our second date, I asked what his deal-breakers were, and he thought for a long time. “People who lie, cheat, and steal,” he finally said.

He was telling me exactly who he was, but it was in a code I hadn’t yet cracked.

I’d been accused of having hard edges in the past, so I wanted to be different this time. I’d be extra patient, more vulnerable, let my guard down faster.

I never imagined doing so would eventually lead me to nearly 20 other women who had been harmed by the same man. Or a trail of lies and deceit that began with a stranger’s TikTok video. But, as Jake might have said, that was future Haley’s problem.

I was, to be honest, a little smug. Because I’d been single for years, people would often tell me I was too picky or try to set me up with men who were wholly inappropriate. I’d held out and it had worked: Now I had a partner who was Disney-prince attractive (literally, he played Aladdin at Disneyland), grounded, kind, athletic, witty, and supportive.

We were a cute couple. He smelled nice. He had a full head of hair and was clean-shaven, a combo that seems impossible to find in this age demographic. He said the sweetest things. He looked at me in a way where the affection felt palpable. He called my cat his best friend. His social life didn’t revolve around drinking. We shared a similar sense of humor. We both loved to lift weights. He liked my interior design and my playlists and my taste in movies. We both enjoyed being competitive and talking trash (lightly) during games of Connect Four.

We were also different enough to keep things interesting. He worked a physical job, while I make a living from typing. He was a rebel, and I’m a rule follower. He was excellent at parallel parking and woodworking, and my skills are mostly in googling things. I did not yet know how handy that would be.

He was at my house one rainy afternoon, upset from having seen old firefighter colleagues he no longer felt connected to, when he got a call from his mom letting him know that his uncle had passed away. I could hear him start to cry in my bedroom. I brought him tissues and wrapped him in a hug. He didn’t let go for a long time. “Let’s just say I dated one girl for two years who never saw me cry,” he said. Later that night, he told me he’d love to be my boyfriend.

Everyone who met Jake adored him. “I love him!” my best friend texted after meeting him for the first time. “He seems so nice and genuine. And very cute.”

He was very cute, but the connection was much deeper than that. “I’m mostly grateful that he’s kind,” I texted a friend in March—a month wherein we saw each other nearly every other day. “I guess that is a quality I value more as I get older.”

By the time my birthday party rolled around, I could hardly believe how well my life was going. I was on the verge of signing a second book deal, the end of my HOA presidency that caused so much stress was in sight, I had a lovely group of friends to gather for my party, and, for once, I had a partner there, too.

In a floating hot tub on Lake Union, everyone went around and said what was special about me. Jake went last. He floundered a bit, and I felt bad—he’s an introvert, and he was thrust into a situation with people who’d all known me a minimum of a decade. But he said it had been an amazing six months and I’d made Seattle feel like home to him, that I was thoughtful, nicer than I think, an incredible cat mom, and clearly loved—and that he couldn’t wait to see what the following year brought.

He didn’t give me a gift or a card that day, but he pulled me into an embrace and told me we’d celebrate when he returned from a trip he was leaving for the next day to visit family in California.

The relationship felt like it was coming together in a meaningful way, but of course it wasn’t perfect. Jake was a sporadic texter, hated making plans in advance, and usually showed up late. Early on, he disappeared for three days one time, and he’d often abruptly drop off in the middle of a text conversation. He told me he didn’t like communicating on his phone, and it seemed true—in person, I rarely saw him check it. But he promised he’d get better over time, and he did.

Nothing spiked Jake’s heart rate, a great quality for his job as an EMT but perhaps less desirable in daily life. He’d been warned multiple times not to park in his apartment’s garage, as he wasn’t paying for a spot. And yet he ran an errand while I was there one afternoon and parked in the garage when he returned. When we went to leave that evening, he had no truck—it’d been towed at a $450 expense. I told him the garage needed to be off-limits in his mind. “If it were just me, I wouldn’t have gone into the garage,” he texted me later. “Also, nothing is off-limits.”

I wondered if I could deal with that long-term, the blatant lack of regard for rules and the squandering of resources for basically no gain. He did it solely to rebel, because he hated being told what to do. He also subtly tried to shift the blame to me, as if my presence three floors above magnetized his truck into the garage.

He cared about appearance more than most—he denigrated an ex’s husband for being “ugly” and refused to carry his driver’s license, even when he was driving, because he was embarrassed by the photo. In fact, he hated all photos of himself to a degree I thought was strange. He worried his cheeks were too red and his mouth was too small. He told me I was stunning but called himself mid, a statement I knew he couldn’t possibly believe. If he had a choice between being on time for a date and getting a haircut, he’d get his hair cut.

This all felt minor, though. My only real cause for concern was when I saw that his Tinder account was active a few days post-exclusivity. He claimed a technical glitch was to blame, and though I was skeptical, he reacted so well to the conversation that I trusted it wouldn’t be an issue moving forward.

Before Jake left for that trip to see his family in California and attend his uncle’s funeral, I asked him to check in once every 24 hours while he was gone, just so I knew he was okay. But on my actual birthday, he didn’t call. Didn’t even text until 5:30pm. The day after that, I didn’t hear from him. Then the following day, he wrote, “Hey morning you, sorry just busy with catching up with family. Today is the procession/funeral. I’ll just check back in with you once I’m back.”

I didn’t even know when that was supposed to be.

On a hunch, I logged into my long-paused Tinder account and saw his distance was 121 miles away—not nearly far enough to be California.

I sat uneasy with this information for two days until Jake texted me a photo of an airplane, presumably his flight home. A tiny, slightly blurred logo was staring back at me: the striped heart of Southwest Airlines. The problem? Southwest doesn’t fly straight to Seattle from Ontario, California, the airport Jake told me he was flying out of. “Connecting flight to SF! Then to SEA,” he said when I brought it up. That just made it worse. Southwest doesn’t have nonstops between Ontario and San Francisco or San Francisco and Seattle, either. No leg of the journey he was supposedly on was possible.

I’d been contemplating going to the airport to surprise him when he arrived. Now I clung to the slim hope that this was all a misunderstanding. Maybe he confused San Francisco with nearby Oakland? Perhaps he meant SMF, the Sacramento airport, instead of SF; there was a route there that was plausible. But then he “landed” far too soon to have made it from Southern California to Seattle with a transfer included. There were no possible excuses left.

It was time to bring out my reporter side. I wanted the truth, even as I knew I did not want the truth.

One of Jake’s favorite stories to tell was the one about how he played Aladdin at Disneyland when he was in college. It made a lot of sense—he had that Prince Charming kind of face, with long eyelashes and chiseled features. He’d always related to the character’s life as a “street rat” and often referred to himself that way. (I later found out he had a penchant for stealing avocados, a very Aladdin thing to do.)

So when I saw the Broadway version of Aladdin was coming to town, I knew I had to get tickets. Unfortunately, they were sold out, but I kept checking back, until one miraculous day around 10am, a small block of seats was released. I ran up to the Paramount Theatre to nab a pair. We joked that it was a good thing we were in the balcony, just to curb the temptation he might have to jump onstage if this Aladdin weren’t doing the role justice.

A week beforehand, I even wrote him a parody version of “A Whole New World” to enjoy while at work: “I can open your eyes / Get impossible tickets / Had to trudge through the thickets / So we could sit side by side.”

But in the days leading up to the show, the investigative seeds I’d planted during Jake’s mystery trip were starting to bear fruit, and it was instead my eyes that were opened. I don’t want to share all the details—mostly because he may read this one day and I have no intention of making him a better liar—but through social media, I found a woman in Seattle whom Jake had dated, then ghosted. At the time we had confirmed exclusivity, he told me he had not seen anyone else since moving here, so I realized he’d been lying about more than just the trip.

A day after that, my heart began to race as I read several social media posts about a man who was a chronic cheater and liar—and even before I scrolled to the bottom to see the photos, I knew in my gut it was Jake. Then came the TikTok video. A very young, very intense woman stood in front of the camera, seething with anger as she told the story of how she dated him for two months and was head over heels in love, only to be broken up with out of the blue. A week later, she was DMed by his long-distance girlfriend of 10 months, who’d found an eyeshadow-stained makeup wipe by the trash bin while moving her things into his Portland apartment. She’d been in the process of uprooting her life, having gotten a fully remote job so she could be with Jake.

As pictures of them together popped up on the screen, I honestly thought I might evaporate.

I watched that TikTok video over and over again to convince myself it was true. But that was only the beginning.

To unravel the mystery of who Jake really was, I ultimately talked to more than a dozen women who have been hurt by him—most in the past year alone, although I found people from multiple eras. I was, of course, not the first person he’d dated in Seattle. He’d been cheating on me the entire time (physically with at least five people, emotionally with too many to count), and also with me, as he had a newly minted full-fledged girlfriend when we went on that first date. He continued to ask women out well after we were exclusive and official. When one “fire buddy” was in town, that was a woman from Portland he’d been stringing along, telling her just enough to keep her on the hook without ever committing. She left 24 hours before I visited his apartment for the first time.

She came back once more, the night before he met my entire extended family at a celebration of the one-year anniversary of my grandma’s death. They had unprotected sex and agreed to a trial run of long-distance dating. The next morning, he told her he had a work training and then showed up late, nearly missing the ferry to meet me and my mom. She’d planned an entire itinerary for him, complete with stops at the fire departments he might want to apply to. He told me that evening it had been the perfect day.

Last fall, he was dating more than half a dozen women at once, all of whom were under the impression that he was not seeing anyone else. Even after they all discovered it, many stayed in his life in one way or another.

He only fled to Seattle in the first place to escape his reputation, and to get a new job as an EMT after being forced to resign from his firefighting position in Oregon for dishonesty.

He lied about things big, small, and in between. When we first started dating, he told me he had an apartment in Tacoma, but he was actually living in the camper on his pickup truck. He sent photos of a trip we took to Bellingham to several other women, pretending he was alone. I heard stories of him blowing past park rangers when they asked for the permit fee, sneaking into movies without paying (and lying through his teeth when getting caught), and trying to steal groceries when his card was declined.

Even his origin story was a lie. He told me, and everyone else, that the love of his life asked him for a break, then began dating his coworker the next day. Heartbroken, he quit his job and fled to Alaska to become a fisherman. The real story? She kicked him to the curb after discovering he was soliciting naked photos of women online.

Most horrifyingly, when one girlfriend was in Jake’s apartment, she found a pair of panties under his mattress. He explained them away as being from before they were together. She told him if he were cheating on her, it could literally kill her—she has an autoimmune disease. He’d even sat in on one of her doctor’s appointments. He said that his aunt had died of the same condition, and that he’d never put her at risk, would never cheat on her. But he continued to do so for another six months, until she had definitive proof and her world came crashing down. “The trajectory of my life has been totally altered,” she told me. “It’s hard to fathom.”

“That experience drove me to the point of needing professional help and medication,” said another woman who dated Jake. “I was hoping that by now he would’ve died in a fire, but I’m so sad to hear that he’s instead out there still doing the same shit and hurting women.”

“He was so good at being brutally honest in a way that made you feel not great about yourself,” said another.

“The amount of gaslighting I dealt with still has my head spinning,” said another.

“He literally wrecked me,” said yet another. “I have never felt so betrayed in my life.”

As I was putting all the pieces together, Jake was in San Diego (for real this time!), so I needed to wait until he returned to do anything about these revelations. I focused on acting normal by text and phone while I wrote and rewrote my breakup speech. I’d learned that other women rarely got a chance to confront him in person—once he suspected they were onto him, he’d avoid them unless he thought they were ripe for manipulation. So in my final act of kindness (mixed with a little subterfuge), I let the Aladdin date stand.

I got dolled up and met him at the theater. He showed up in a suit, on time for once, striding toward me with a look that would’ve made anyone swoon. He didn’t like dressing up, but he’d done it for me—was I really about to let him go?

I was. But first, I had a show to watch. Tears slowly spilled from the corners of my eyes a few times, but he didn’t notice. Instead, he chatted excitedly about our plans for the summer. If he bought me a onesie, would I wear it and go on a onesie date with him?

Afterward, I suggested some bites and sips in the lobby of the Fairmont Olympic. I wanted the breakup to be in public because, I was quickly realizing, I didn’t know this man at all. He ordered the patatas bravas and asked me if he was my physical type. It was such a weird topic of conversation for two people who’d already been dating for months, but I answered yes through a tight-lipped smile, trying to contain the bile forming in my stomach. “You go for tall, dark, and handsome? With broad shoulders?” he asked. Our thighs were touching.

As he finished his appetizer, I launched into my carefully rehearsed speech. I cataloged every lie I knew. Told him how it sickened me that my family and friends welcomed him in because they trusted me so much, and now my word and judgment were tarnished.

I said he was messing with people’s real lives, that he needed real help, that I never deserved this, but that he didn’t either. “You might not realize it, but you are in pain. Right now, your contribution to the world is pain.”

I asked him to skip the denials and to simply answer a few questions truthfully. He sat buffering for 60 seconds, a hundred microexpressions crossing his face, unable to process what had just happened. Jake hadn’t been fooled before, hadn’t walked into a trap. Here in a fancy hotel, wearing his best suit, he had no choice but to listen. A whole new world indeed.

He relied on old friends like denial, minimization, manipulation, and straight-up lying to explain everything away. He’d never officially dated any of those other women; they just got attached to him because he’s so polite and charming. “I’m a good listener, so women think they’re in something deeper with me than they really are,” he said.

“Jake, I’m pretty sure a woman knows the difference between when she’s moving in with you or not,” I replied.

He was not cheating on me, not asking other women on dates, and not making up a story about California. Yes, he had remained on Tinder, “but not for the reasons you think.” Sure, he’d cheated on three past girlfriends, but “there are gray areas, Haley.” Everything, until the very end, was a lie.

Over the course of the nearly four-hour conversation, I didn’t learn anything about what I really wanted to know—why he did this, why he picked me, whether anything at all about our relationship was real. The chilling fabrication about a funeral that he did not attend remained unanswered for. The flirting, dates, and sex that happened with others while we were in a committed, monogamous relationship went unexplained. I did learn, though, that he’d used my toothbrush twice.

When I finally dismissed him, he stood gazing at me through a glass window with puppy-dog eyes, one last chance to play the good guy.

I woke up the next morning feeling utterly confused. I almost started to believe maybe I’d done something wrong. I had not, unless your bad list includes always having his favorite Trader Joe’s beverage on hand, doing a huge amount of research about his career to help him find a job, and making sure to always hug him immediately upon seeing each other, the one request he’d made of me.

Before our conversation in the lobby of the Fairmont, I didn’t have all the details. Just enough to know it was over. As I reached out to other women, the bigger picture emerged.

Through their stories, I began to grasp the mental gymnastics that can happen when you want to trust someone. The rationalizations made sense to each of them at the time. Yes, I’ll continue to have unprotected sex with this man who’s admitted to sleeping with multiple women at a time because he told me his last STI test was negative. Yes, I’ll believe I gave him this hickey on his chest even though I know I haven’t kissed him there recently. And yes, I’ll fall back into his bed again, even after confirming he cheated on me, because I still can’t really believe this all happened.

That’s the cognitive dissonance at work, says Thane Erickson, a professor of clinical psychology at Seattle Pacific University. Our brains are like thermostats constantly checking the temperature on ideal behavior vs. current behavior. If something doesn’t match up, we’ll try to move one thing or another to make sense of it. “We have a need to want to trust. There are people who will externalize and say, ‘This is a bad person,’ but a lot will do the opposite, where it’s safer to blame yourself and give others the benefit of the doubt,” he says. “People feel, ‘I’d rather live in a world where the world is predictable, but I’m causing problems, rather than a world I can’t predict.’ That’s a scary world to live in.”

I was not immune. After all, I had brushed away his lies about being on Tinder.

The strangest discovery of all may have been that, despite all the sex he pursued, he didn’t actually seem to enjoy it. He wanted the women to want it, but that’s where the desire ended. The pleasure came from the power it gave him. There was never true connection.

On the flip side, he wasn’t pushy. He let his partners go at whatever pace they preferred. He was otherwise always a gentleman, willing to bring over his tools and help fix something around the house. He made beds, cooked breakfast, opened doors, and left sweet notes. He talked about future plans with apparent conviction and excitement.

The women were often vulnerable in some way—immunocompromised, recently divorced, diagnosed with serious mental health conditions, or even just very excited to have someone like Jake pay attention to them. Many told me they didn’t feel like they deserved him. In most of the stories, I could see the love-bombing clearly from the outset, but he was much subtler with me. In reckoning with everything, one of my nagging thoughts has been to wonder how I fit into the puzzle, what my vulnerability was.

I’d naively assumed cheating was something that wouldn’t happen to me. I don’t associate with dishonest people, I have high expectations, and I’m good at clocking lies. I’m an observer. And yet here I was, duped just the same as everyone else.

My sister, the queen of debriefing after every family event and reality TV episode, told me he wasn’t even worth analysis. “It’s like going into a hoarder house and trying to decide why someone made their decorating decisions,” she said. “You can’t.”

Technology made it possible for Jake to cycle through women at a breakneck speed. It also made it easy for him to get caught. In a world that’s increasingly connected, it’s impossible to escape our digital footprint. Information that helped me piece together his indiscretions was everywhere, from TikTok and Instagram to Facebook Marketplace and mobile payment services to online funeral sites and LinkedIn feeds. In the course of looking for answers, I’ve collected photos, videos, PDF documents, voice memos, and conveniently time-stamped text threads.

For someone who claimed to not like his phone, Jake was downright addicted to dating apps, using them the moment he left someone’s home, when he was tucked away in a bathroom, or in his truck on the way to a date. He’d create a long list of matches, some of whom he wouldn’t respond to until months later when a spot on his roster came available. He could not stop—and never, in his mind, had a compelling enough reason to.

“Every behavior you ever do leaves a mark on your soul, it leaves a groove,” Erickson says. “That groove gets easier each time you do it. People dabble and try things out, and if it works, it gets repeated.”

Technology also brought me a community of sorts, a group of women I would have never met otherwise. They come from all walks of life and span the age range from just out of college to their early 40s. (Jake is in his mid-30s.) They work minimum-wage jobs and in careers that require graduate degrees, they have kids and no desire to ever have kids, they live with roommates and own their own homes, they dated on and off for four weeks and on and off for four years, they wanted nothing more than a casual fling with him, and thought they’d get married one day.

Some did not want to revisit the trauma more than briefly, and others spent hours telling me their stories. More than one became suicidal in the aftermath of his destruction. Many have checked in on me, offering support and friendship. In all cases, I am grateful they were willing to speak up, however they did so—without their courage, I might still be dating him. If there’s one silver lining, it’s the knowledge that women connecting can be incredibly powerful.

Investigations are great for identifying the who, what, where, when, and how. What’s harder to get at is why. My brain has spent weeks gnawing at that question. I know it was Professor Plum in the study with the revolver, but what made him pull the trigger?

The problem with people who lack empathy is that they can do whatever they want whenever they want without their conscience chiming in to say, “Uh, you sure about this?”

“The shameless know us much better than we know them,” writes psychologist Martha Stout in The Sociopath Next Door—a book I read because, for the first time in my life, I felt like that was what I could be dealing with. “We have an extremely hard time seeing that a person has no conscience, but a person who has no conscience can instantly recognize someone who is decent and trusting.”

Image: Pete Ryan

Cheating of any kind has long-lasting ripple effects. Chronic cheating exists in a category by itself, though. These are not basically decent people who get lost somewhere along the way. These are people who never intend to be faithful, not from the first date, not from the first kiss, not from the first time they say “I love you,” not when they ask you to move in, not when they stand at the altar.

People without a conscience don’t play by the same set of rules as the rest of us, and so it’s hard for everyone else to comprehend their motivations. “The average person is not very experienced in dealing with people who show up to lie and charm and manipulate,” Erickson says.

Even when these people are finally caught, we rarely call them out. We simply want to get out of Dodge. We are conditioned to be polite over confrontational. This is especially true for women.

“A part of a healthy conscience is being able to confront consciencelessness,” Stout writes. “When you teach your daughter, explicitly or by passive rejection, that she must ignore her outrage, that she must be kind and accepting to the point of not defending herself or other people, that she must not rock the boat for any reason, you are NOT strengthening her prosocial sense, you are damaging it—and the first person she will stop protecting is herself.”

Many well-intentioned people told me to wash my hands of the whole situation and forget he ever existed. You can’t win against someone without a soul, they said. And maybe you can’t because you aren’t even playing the same game—but you can certainly try to stop the behavior, or at least slow it. You can warn others about him. And you can help someone else recognize the signs in their own relationships, and empower them to take action. If you have a platform, you can use it.

Jake liked to call himself a lone wolf. (His dad, on the other hand, said he was “a wolf who’s just alone,” which I found hilarious in a parents-don’t-pull-punches kind of way.) As part of his housewarming gift, I got him a watercolor bookmark with two wolves traversing a snowy landscape. “You can still be a wolf,” I told him, “but you don’t have to be alone.”

Wolves are excellent predators, often able to take down deer, elk, and moose without the benefit of a pack. They’ve even been known to wear down bison, although only vulnerable ones. Sometimes even the most talented of hunters bite off more than they can chew. 

 

In some ways, it seems I got a pretty good version of Jake compared with other women I spoke to. He texted more, rescheduled less, forgot fewer details, and treated me to more dates. He never criticized me, the way he did with so many of the others. My ego wants this to mean something, but the more evolved part of me knows it doesn’t.

In the immediate aftermath, I couldn’t help but wonder what was wrong with me, which is exactly what he’d wanted. What if I had done this or that differently? Did I respond the right way when he told me something vulnerable? Could I have been more lovable? Sexier? Sweeter? Fill-in-the-blank-er?

It is supremely unfair that in his life, little has changed. The day after I ended it, I’m sure he consulted his apps, loaded with matches, chose another one, and had a date scheduled as soon as he could. Who knows what he’s told people about me, if he’s even acknowledged me at all. If the past is any indication, I may simply be wholesale wiped from the record. If I remain part of his story, the ending will certainly be edited.

I, on the other hand, will never be the same again. I’ve lost 16 pounds, my trust in myself, and the ability to see an ambulance without wanting to vomit. It was gratifying to find someone who ticked nearly every box I had. It was heartbreaking to realize he only did that because he was a shell of a person mirroring what I wanted back to me.

Still, in those moments when I felt like I would’ve rather been stabbed with a knife than betrayed in this way, I realized something: Shame thrives in secrecy. And I will not feel shame about this. Sadness, rage, confusion, despair, disgust, disappointment, bewilderment, and grief, yes—but not shame.

That is a feeling that belongs to him alone, and I hope one day he’ll reckon with it. In the meantime, I am a princess battling an imposter prince, a bison too powerful for a wolf to wear down, and a journalist who can easily confirm where Southwest Airlines flies.

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