‘My Cheating Boyfriend Kept Cheating’

We were in therapy! He pledged his devotion!

Man at Table (1911) by Marc Chagall


I am writing to you less than eight weeks after I sent you “Want to Stay.” I noticed you did a follow-up letter with the same person recently and I thought that was really cool and nice. I also thought it was kind of annoying that the writer wrote to you again, but now I understand that desperation and I’m also being annoying. I won’t be so judgy in the future.

I stayed. He got therapy. Our relationship felt amazing! All the things you said about shared healing and energy and vulnerability were true. God, I was in heaven!

Eventually I had a gut feeling something wasn’t right. I went digging and found more than ten solicitations to women for sex, dates, etc., all done within five days. I didn’t go past ten because I just couldn’t. I packed my stuff (he was in the shower when I snooped), left dinner cooking on the stove, and left for good. He called and tried to get me to come back but eventually gave up and disappeared.

WHAT THE FUCK? How is it possible that the cheating is WORSE than I thought? He controlled this nice, neat narrative to me about how his bout of infidelity was due to some serious childhood issues and that he’d had it with himself and needed help. He booked the therapist! We went every week! We had great conversations about his progress. BUT THIS WAS LURKING IN THE SHADOWS THE WHOLE TIME! WHAT THE FUCK!

I don’t regret what I did by sticking around. Like you said, the most important part of it was I made my own choice and I owned it and for the first time in my life, really just let that empower me. But I did not expect THIS dark and gross twist and turn. I mean the relationship is over, that’s not the question of this letter. It’s no longer “Should I stay?,” it’s now “How do I regroup after being with a complete sex addict, master manipulator, and liar for multiple years?” And yeah, our relationship had its issues but I had no idea the depth of this. None. And I’m smart and don’t have my head in the sand.

I spoke to his most serious ex. His name is still on a mortgage with her, poor thing. He bought a house with her (which he failed to mention to me. - that would have been a fun credit check) and the day after moving in, told her he was in love with another woman from the internet (!!). I know that’s my future if I stay, so staying is out of the question. But the question is HOW DO I MOVE FORWARD IN LIFE KNOWING SHADY SHITS LIKE THIS LURK AROUND EVERY CORNER, READY TO TAKE ADVANTAGE OF MY MOST BEAUTIFUL AND VULNERABLE PARTS? No, he didn’t take my magic and he never will, but I am fearful as all hell of humanity right now, as if I needed another reason. Ugh.

Definitely Not Staying

Dear Definitely Not Staying,

I am so sorry for what you’re going through right now!

I hate to admit this, but I just rushed to read my original advice, praying that I didn’t tell you, “Stay with your cheating ex because hell, what could go wrong?” You’d think I’d know that wasn’t the case, but I’m sort of in this tweaked place right now where life looks very short and learning and growing and trying new things seems much more important than playing it safe.

You chose not to play it safe. And now you’re in a massively tweaked place, too. But instead of turning against what you’ve been through and all that you learned from it and attaching a reductive moral to it (“MOST MEN ARE EVIL! YOU WILL NEVER BE SAFE!”), I want to challenge you to open your heart and make yourself vulnerable in this moment, the way you did when you were in therapy with your ex, the way you did when you forgave him, the way you did when you found a way to reconnect and cultivate hope again.

Paradoxically, feeling sad and mourning this loss fully and showering yourself with compassion is the best way to stay safe. Deciding that the world is filled with bad men who will do nothing but lie and cheat and fuck up your life is the least safe choice possible, because it will fog up your windshield and break your compass and make it very hard for you to navigate forward.

Why? Because fixating on compulsive cheaters and liars like your ex when you believe in living a passionate life of love and connection is like telling yourself that a world full of vicious stray cats that will scratch your eyes out will prevent you from ever petting a cat again. You don’t need to think about the angry cats. You’re looking for a cat who loves to be petted and can be trusted not to scratch your eyes out. They exist. Don’t focus on apples when you want an orange.

Like I said in my original response to you, your ex is an addict and so are you. He’s addicted to the fix of new hook-ups and sexual intrigue and he also might be a pathological liar or a sociopath? I mean some people enjoy lying. So going to therapy and confessing his sins and resolving to do better might’ve been part of the fun. You landed in the middle of a serious horror show. The emotional whiplash from that must be extreme. You should consider going to Al Anon or a support group for women, because processing this anger and grief is going to take some time.

The positive here is that this could be your personal rock bottom, if you open your heart and look around at where you are. Because in your first letter to me, you said that you’ve been giving away your power to men for your entire life. You tend to shrink and make a man your top priority. You tend to accept whatever a man brings you, and if he’s slightly dissatisfied, you work harder to please him. And even though you changed and grew and seemed to love a new kind of man, you’re facing another nightmarish reality. You’ve leveled up to a new kind of deceit that’s hard to detect. Unfortunately, the most awful sorts of men alive can often sniff out a former people-pleasing love addict like you in crowded room.


But there are still plenty of men out there who love women who know how to please themselves, stand their ground, and state their needs directly. Just because many, many men find that distasteful doesn’t fucking matter. You must stop staring at the bad apples if you want to find an orange.

Likewise, if I had a dime for every woman who’s told me that women become invisible as they age, and most men are hellbent on fucking younger strangers, and most men like younger women in general so don’t think for a second that you’ll be dating happily past the age of 40, I would be rich as Midas. What I keep wondering is: Why are we talking about the same handful of broken motherfuckers again? That’s like being a huge NBA fan but all you talk about is shitty pick-up players who have no defensive game and can’t sink a lay-up from right under the net.

You’ve been disastrously and catastrophically mowed down by a careless, possibly sociopathic, definitely very fucked up man. Don’t you dare build a religion around it. Build a religion around hope and forgiveness for yourself instead. Build a religion around softness and wonder and compassion. Embrace this electric, scary feeling that you’re having while you’re grieving. Let it all in. And listen to me very closely: There are amazing men in this world.

Lots of men want to be with their intellectual and emotional equal. I’ve been alive for a while and I know that for a fact. Age is not a thing for most men; they just want someone who gets them and listens. Most men don’t fixate on a woman’s physical flaws. They will work with what you have, as long as you excite them and turn them on in general. How do you become an exciting turn-on of a human being, turning yourself and the whole world on with your goddamn smile like Mary Tyler Goddamn Moore? By embracing who you already are instead of always working so fucking hard to be better and please people. And by embracing reality, which is full of apples and oranges, violent cats and affectionate cats, crappy men and amazing men, malevolent orange clown leaders and honorable leaders, people who tell reductive, defensive, rigid stories and people who try very hard to welcome in the good and the bad each day without hiding under the bed.

Life gets hard again. I’m publishing your follow-up letter because that’s the theme I want to pound home to everyone who reads this column, because I think our culture and the people in it have been telling each other fantastical stories about permanent happiness for decades now. I spent half of my life hoping to cross some magical finish line where everything would be happy and perfect when I should’ve been living in reality and allowing some room for disappointments, sadness, unexpected twists, longing, regret. All of those bad things bring gifts along with them, always, but you have to stay vulnerable and open in order to receive them. Refusing to accept that life gets hard, over and over, is similar to telling the story that all men are bad and should be avoided: it keeps you stuck, looking at the things you don’t like and don’t want instead of expanding your heart and your mind and your passions. Life is very short. You must incorporate this pain into your life while also rededicating yourself to learning and experimenting and trying new things. You have to be brave enough to listen to your fears without letting them crush your spirit.

This is a perfect crisis for you, honestly. You were already on the path here when you decided to open your heart wider in the middle of a big crisis, and the path might get steeper from here, but it will lead you to so many incredible discoveries and good feelings and new desires. This is a revolution in feeling and thinking. You don’t have to tell a story about being eternally damned, like so many other people do. I know it’s really fucking hard at the moment. But the longer you manage it, the more you’ll recognize how strong you are, how resilient you are, how flexible and brilliant you can be, when you let the whole world in and STAY VULNERABLE. Make that your religion. Even when it’s impossibly hard, it will lead you back to joy.

Right now, you’re looking at the scorched earth around you, but there’s a fragile seed under your feet, under the soil, trying to grow. Open your heart, pay attention, be patient, and watch what grows here.


You can read my column here every other Wednesday, and you can read it the other Wednesdays on New York’s The Cut. You can also read Ask Molly, written by Polly’s evil twin. Write to Polly: askpolly @ protonmail.com. Your subscription supports all of the above.