Ten things I learned during my time as a Craigslist listener

“It’s just…” his voice trailed off.

He seemed nervous about talking to me, and I could hear the sounds of traffic surrounding his car. “Well, my wife and I haven’t had sex in months. We disagree on how to raise our kids. And now that she’s gone back to school, I find myself having to pick up a lot more slack at home. I’m really unhappy.”

I’ve heard this — or different iterations of similar sentiments — hundreds of times in my five years as an anonymous online listener. What I do is simple: through an ad on Craigslist, I offer to listen to stories that people have never told before. I do it anonymously and for free. My subjects know that I’m not a therapist. We sit down to talk as friends, often over a cup of coffee.

The service I provide is a simple one: I listen; I engage; I ask questions. A month or two into this, I began to ask permission from my subjects to write about their experiences. The purpose was to create an anonymous pay-it-forward confessional where people can learn from each other and perhaps, in sharing their stories, not feel so alone.

It’s not surprising that the vast majority of stories I hear are about love and its side effects — divorce, money, kids, midlife crises, lost loves and missed opportunities, regrets, affairs, and everything in between. Over the years and the span of hundreds of hours of listening, I started to notice some patterns in the stories that people have shared. I’ve kept a list of lessons learned in the last five years — some of them are big picture stuff, others are more specific patterns that I’ve noticed over many hours of listening.

1. Everyone has a secret.

I often find myself asking: ‘Have you told your partner about this?’ Most times, the answer is ‘no.’ I know what you’re thinking — what could possibly be so bad that I couldn’t even tell my partner or therapist about? And you’re right to question it: most of the stories I hear aren’t about atrocious crimes committed or dark childhood trauma, although I do get a fair share of those, too. So what’s keeping people from sharing these stories with their loved ones?

A big part of it is fear of being perceived differently. People don’t want to feel pitied; they want their experiences to build strength, to feel useful. They especially don’t want to become a burden to anyone — even if it’s someone they’re paying to help them sort out their issues — by prattling on about something in a way that feels self-absorbed or indulgent. It’s easy to feel that way when the person who’s listening isn’t invested in your story, or is someone whose job it is to help you sort things out. 

The only thing I’ve found people fear more than pity is judgment, or feeling morally or otherwise inferior to someone else. Giving someone a glimpse of your issues is seen as a power transaction — by showing ‘weakness’ or ‘vulnerability’, you forego the illusion that you’re perfect, strong, a go-getter. Society values the latter, all the while encouraging us to hide our imperfections behind perfect facades. So it is rare, indeed, to find a place where you can unload all your insecurities, hang-ups, and past trauma without fearing that you’ll somehow end up regretting allowing yourself to open up to someone.

2. "I love my children, but…"

It’s the conjunction that piques my interest. One mom told me she wished she’d never had her second baby. ‘It’s just too much work,’ she said. ‘My husband and I rarely have any time together. We both work, and we don’t have family nearby. When the kids aren’t in daycare, they’re with us — so alone time is out of the question.

She went on to tell me that when the second baby came, the illusion of control over her own life went out the window.

I’ve learned that what’s sometimes expressed as resentment towards the decision to have children is most often chagrin towards dwindling choices and growing responsibilities. Although we might choose to believe that escapist daydreams are unique to the most recent generation of adults, they’re not. It’s natural to lament a growing roster of responsibilities, to fear change, or to look at a not-so-distant and comparatively simple past with rose-colored glasses.

What’s unique about this is that many of us also feel guilty for being conflicted about our choices. My subjects whisper these confessions with such shame and expect a reaction of shock or utter horror. They quickly follow up their confessions with — but I love my kids, and they bring so much to my life, and I wouldn’t have done anything differently — eager to skim over their negative feelings to a happier and more easily-acceptable narrative.

3. Just telling your story is powerful. 

And speaking of narrative: one of the questions I get most often is about why I do this —  Isn’t it like you’re giving out free therapy? But you’re not a therapist, right? Well, what’s the difference between this and therapy, then? 

Well, there are several pretty big differences. One that immediately comes to mind is that, because I’m not a therapist, there is no hierarchical separation between doctor and patient. There are also no expectations — the subject is not expecting some revolutionary advice, some life-changing or affirming insight — and thereby, no disappointment. Most importantly, there is no ongoing relationship and it is anonymous. Because most of these meetings are just one-time interactions, there is no inherent fear that their confession might be shared with other people in their lives. 

Finally, there’s something else I’ve discovered: you tell a story differently when you’re telling it for someone. That’s the effect of audience on narrative — subconsciously, you change your story, make it more attractive, more sensationalist — you make it a highlight reel, because that’s what we’re all conditioned to do. So, during these meetings, I tell my subjects to pretend I’m not there, pretend that they’re talking to themselves. I participate when it’s necessary, but my aim is to be sensitive to cues that tell me when it’s important to just listen — just be

Therapy doesn’t always work.

4. Money doesn’t matter…that much.

Studies often cite disagreement over finances as one of the biggest factors leading to divorce. What I’ve noticed as a listener is how often men mention “providing” for the female. To me, that’s significant because it shows that no matter how far we think we’ve come as a society in redefining our gender roles, people often revert to the same old patterns under the guise of anonymity: men bring in resources, women tend the home.

So fights about money are seldom just that — at their root, they’re disagreements and resentments about who should do what, and whether they’re doing it well enough under different societal pressures. A year ago, I spoke to a husband and stay-at-home father who was struggling with his new role as Mr. Mom; he and his wife had been at each other’s throats more than usual. He told me, “I can’t help but feel that my wife isn’t sexually attracted to me anymore because I’m not ‘the man’—I’m not out there, providing for our family; I’m at home watching the kids and cleaning the house — basically, I’m a housewife. It’s hard to find a housewife sexy.”

5. The language of confession

The language of confession is timid (‘I know other people have issues, too, probably way worse than mine…’), passive (‘things were done…’), and filled with fear and shame. Part of active listening is learning to decipher the words that people use, and what these words tell you about their emotional location — are they ready to broach a topic, or is everything still too raw? What’s the dominant feeling — is it shame, fear, anger, guilt? Is this a sensitive topic filled with possible emotional landmines, or would it be okay to gently prod? What does the subject need— to feel encouraged, justified, seen? — and can you provide that? How can you provide it in a genuine, non-contrived, way? 

And sometimes you have to do a few mental calculations — will the subject ultimately feel better for having spoken up? Or does this conversation warrant follow up? Although there is no time limit for meetings — meaning, I can listen for two hours or five, it’s up to the subject — it’s often hard to “fit everything into” one session. And if at any point I feel that more needs to be said but the subject is nearing emotional exhaustion, I always offer a second meeting. The “one (meeting) and done” format is for the benefit of the subject — but if they ask for a follow up, I’m there. And if they ever ask for more hands-on help, I know my limitations as a layperson, and I am always happy to provide them professional references. 

6. Once a cheater, always a cheater…?

I catch people at different points of their affair timelines: before they’ve had an affair — in which case they’re talking to me as a way to get permission to cheat (more on this later); during the affair — and they’re hoping I’ll alleviate the guilt they’re feeling; after the affair and before telling their spouse — in which case they’re wondering whether it’s better to tell or not to tell; and after the affair, after telling their spouse — and sadly, a majority of these are stories of divorce. Most people are either in the first or last category.

You might be tempted to assume that most stories of infidelity are shared by men, but you’d be wrong. Studies and my own personal experience show that women are just as likely as men to cheat. Eventually, one way or another, affairs are discovered:

“Someone I’d broken things off with ended up emailing my wife and telling her everything,” one husband told me.

“I found a text she’d forgotten to erase,” another husband said. “It was directed to J. All it said was: I’m free on Saturday.”

“I’m not sure how she found out; she just confronted me with information and then kicked me out of the house for a year.”

“The lady I was seeing ended up just telling her husband that we were sleeping together. I was expecting him to ask for a divorce but to my surprise, he fought for her. I ended up sending him a desperate e-mail in the middle of the night, telling him I was in love with his wife.”

“One day, our text messages got crossed, and I put two and two together and realised he was looking for a partner on Craigslist,” another woman confided.

In my experience, relationships that survive affairs are an exception, not the rule. Stories of infidelity are hardly ever just the accounts of people who are hardwired to cheat, can’t help themselves, and end up making regrettable mistakes. There’s much more nuance to it, often involving emotional and physical alienation of one or both spouses, and other factors — finances, children, career, sex, lack of communication — that push a spouse to cheat.

As someone once told me, “People who are happy in their relationships don’t cheat. It’s not something a content person in the right frame of mind would do — it’s an action borne out of extreme unhappiness.”

7. Sex, sex, sex.

A vast majority, if not all, of the stories that people have shared with me about their relationships have featured one chief complaint — “We’re not having sex.”

In my experience from listening to these stories, the lack of sex is often a physical side effect of emotional unhappiness. No one has ever come to me and said, “I love my spouse, I’m 100% happy in my relationship, we have no issues, except that we just don’t have sex.”

It’s always so much more than that and sex — because it ranks differently in different people’s priority lists, and because it’s an easily ‘measurable’ metric (i.e. ‘we’ve had sex once in the last six months’) — comes up in almost every conversation as a complaint: there’s never enough of it.

The fact hasn’t escaped me, of course, that I’m collecting stories from people who, for one reason or another, find themselves looking through the Craigslist personals ads. So admittedly, I might be getting a slightly skewed look at American sexuality.

Due to the source of these stories, the past two years have also served as an education on fetishes. A while ago, someone emailed me about his adult baby fetish; I’ve spoken to a guy who identifies as part of the female supremacy lifestyle; a woman who worked as a call girl admitted that her weirdest experience had been with a client who insisted that she sit on balloons and occasionally, pop them with her thighs.

Although it’s a relief to hear about stories that aren’t always so serious and heartbreaking, it’s only momentary. I remember vividly a conversation I had with someone who admitted for the very first time that he thinks he is gay — he often frequents Asian spas and has unprotected sexual encounters with men. He’s also married with children. I remember, too, the guilt-racked account of someone with phimosis who had cheated on his wife as an attempt to get over his physical hangup. And it’s not just men: one of the most controversial stories (on social media) was shared by a woman who had cheated on her husband; as a result, one of her children refuses to have a relationship with her.

8. The particular is in the universal 

You must hear the same thing over and over again? Doesn’t it ever get boring? Don’t you get tired of it?

Without a doubt, there’s something about my personality that probably makes me better suited to doing work like this. If there’s something that I can say with absolute certainty about the past 5 years is that none of it has been boring. On the contrary, even if I’ve heard a story about cheating a million times, it’s still interesting. Why? Well, because the particular is in the universal, and vice versa. What’s thrilling is that even a story that could be easily labeled as “cheating” has so much nuance, so many unexpected feelings and complexities — by the very end, you might find yourself wondering how to possibly encapsulate it into a shallow category. 

On the other hand, even the most complex stories connect us all to universal HUMAN feelings. You might feel so wrapped up in your own feelings that you’re tempted to think, for a small second, that no one alive would ever understand what you’re going through. I’m here to tell you, trust me, they would. That’s what’s truly amazing about a project like this — it brings into focus how diverse and, simultaneously, truly alike we all are. 

Which brings me to my next point...

9. Attraction of people with the same wounds

When I first decided to write down the stories I was listening to, it was because I was hoping that they would find other people who needed some comfort — story twins, if you will. 

In your daily life, I’m sure you’ve met someone who just gets you, in a complex way. They understand your fears, your likes, your dislikes. And once you dig in a little more, you find that this person is very similar to you — they’ve gone through some of the same experiences. Being friends with someone who understands you — it changes things. It makes you feel seen and heard, it makes you feel accepted, and it makes your particular story feel less devastating because you’ve shared it with someone else — someone who has also survived it.

This is, after all, the crux of support groups like Alcoholics Anonymous and Al Anon. It’s about finding solace and support in people who have the same wounds as you. And that’s an extension of what Craigslist Confessional offers: a connection with a stranger who has a story just like yours. 

10. Empathy is... 

This is an email I get at least once a week: I want to be a listener. I want to do what you’re doing. Can you tell me how?

And my answer is simple. If you’re sending me this email, or finding yourself wanting to listen to others, you already know how. The empathy, curiosity, and drive to undertake a project like Craigslist Confessional is within you. 

Of course, it’s not easy. In fact, it’s the hardest thing I’ve ever done. The emotional toll that listening takes is immense, and it requires a steady diet of self-care. You’re no use to others if you are unwell, worn out, anxious, unsettled. So doing Craigslist Confessional has meant that I’ve also had to undertake a ton of self work and upheaval. Learning about others means learning about myself — my own feelings, fears and shortcomings. And if I hadn’t been up to doing the work it takes to come to terms with some of my own faults, then this project would have been a bad idea. Because coming face to face with the stories of others also means facing your own demons — and they don’t just go away. 

So, how do you become a listener? Just start. Listen to a friend or a loved one. Create a safe space for them. Give freely of your time, patience, and empathy. Withhold judgment — yes, in all cases. In fact, I challenge you, as you’re reading through people’s lives, to not let your initial feeling towards them be judgment. Judgement makes people retreat; it rebukes their attempts to connect with our fellow humans — it makes us strangers to one another. It’s a fearful world to live in, one in which we run parallel to our loved ones, never finding an occasion to reach out and offer solace, consolation, understanding, and love.

And be ready to tackle some of your own shortcomings along the way. It won’t be easy, but I promise you, it will make a positive difference in your life and that of others. 

Finally, keep this in mind: you don’t change the world overnight. Showing kindness is incremental — you hide a little bit of it in everything you do throughout your day — but it is powerful. Please read these stories with the aim of making a little bit more space in your heart for others who, albeit different from you, are just as worthy of your love. That is, after all, the purpose of Craigslist Confessional.