Ask Polly: Is My Boyfriend Bad News?

Ian McShane as Al Swearengen on <em>Deadwood</em>.
Ian McShane as Al Swearengen on Deadwood. Photo: HBO

Get Ask Polly delivered weekly.

By submitting your email, you agree to our Terms and Privacy Policy.
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Dear Polly,

I admire your style and attitude and on-point advice. I know this sounds very brownnose-y, but I mean it. I just sent my dad the Al Swearengen quote from “How to Write” because we have some hilarious father-daughter bonding memories of watching Deadwood. But this letter is not about him, it’s about uncomfortable stuff happening with my current boyfriend regarding a married woman. Ugh!

My boyfriend is a decade older than me, making him almost 40, which I had thought would mean I would finally be dating someone with enough experiences under his belt to have a developed sense of responsibility to others, increased emotional maturity, and perhaps an understanding that relationships take compromise, et cetera. I’m starting to wonder if I’m dating a big baby, or if I’m the big baby.

Before I met my boyfriend, he had an affair with a married woman who has a small child with her husband. This woman and my boyfriend are both artists. Their affair lasted several months and ended six months before I met him. He says he asked the woman to tell her husband and she never did, and eventually he told her to leave him if she was unhappy, but to do it for herself and not for him (my boyfriend). After that, they lost contact, maybe without much closure. When I met him, he’d dated other people, but he’d talk about her often, and with bitterness. I had to tell him, finally, to stop because it made me uncomfortable. I know, red flag No. 1.

Five months into dating, the married woman comes to town. My boyfriend tells me about it, says she wants to see him rehearse his work, and asks me if it’s okay. I feel total panic, but I know how to act like a normal human so I voice my concern and discomfort and then decide it would be a good exercise in trust for our relationship. They met, I talked to my boyfriend after, he said they just hung around and she asked him out to dinner, which he declined because “it seemed she still had the affair on her mind” (his words). Weird, but she’s gone, it’s over, fine and done.

Two months later, she’s in town again, and this time my boyfriend is a little less understanding of my feelings, a little more sarcastic, maybe not as open. My boyfriend asks me if he can go, we talk about it, I say I’m uncomfortable but don’t put my foot down. I was curious what he would do without me giving some “crazy girl” ultimatum. In the end, he didn’t tell me which day he was seeing her or contact me until later, when he, the ex-lover, and several mutual friends were at a bar. He sent a text asking me to join if I wanted to. I felt panicked and very left out. Again, I know how to act like a normal human but I don’t feel good.

Here’s the thing, Polly. It’s not that I think he would CHEAT on me. It’s something much subtler. It’s knowing that my partner would put himself in a situation to even flirt with someone he previously had a relationship with that involves ongoing deception, as she still hasn’t told her husband about the affair.

Oh but wait, there’s more! After this second meeting, I find out from a mutual friend that the married woman only discovered I existed because my friend told her, and that my partner had had several phone conversations with her over the months we were dating but never mentioned me. I tried to talk to him about it and he *exploded* with anger. He said weird nonsense like “I’m trying to protect her” and “I can’t tell you what’s going to happen in the future.” To be fair, in calmer conversations he has said he wouldn’t be with her even if he and I weren’t together. It’s confusing because he says contradictory things.

Anger is always his go-to emotion. I’m asking him to work on it, in therapy, if he wants to continue seeing me. But beyond that, it is important to me that we have shared values about what is ethical, and I don’t think it’s okay to sleep with someone or have an emotional affair if other parties are involved who would be deeply hurt by it. My boyfriend seems to think he didn’t do anything *wrong* because he was single when this took place.

This woman will be back in a few months, and I’m at the point where if he sees her again, even if only for two hours twice a year, I might leave. The anxiety is too much for me. I can’t decide if I’m setting a healthy boundary or if I’m an obsessive lunatic who’s preventing herself from being more open-minded and accepting.


Not the Other Woman

Dear NTOW,

It sounds like you’re feeling less than your full fucking self, and for good reason! The hour requires some unvarnished words and since you made mention of your passion for Deadwood, David Milch’s brilliant portrait of the Wild West (largely unsung and partially unfinished thanks to some big-city cocksuckers at HBO, who’d sooner brand their own foreheads with a flat iron than allow a man of the pen to complete the masterpiece for which his name will henceforth be praised), I’d like to sally forth in a style befitting the scoundrels, whores, dirt-worshippers, and hoopleheads of that melancholy town. Be forewarned, though, the language herein might lead some to imagine that yours truly has been pillaging Doc’s stash of chloroform, more typically reserved for offering animals a merciful exit from this mortal plane. Suffice it to say that skeptical cocksuckers and those with delicate sensibilities might be well-advised to seek respite elsewhere. You can help your delicate sensibilities by turning the fuck away.

But let’s make haste to address the matter at hand: This fancy big-city artist boyfriend of yours, always off somewheres on a tear with his married ladyfriend, this hapless ne’er-do-well of violent temper, oversensitive to the merest slight from your tongue, yet armed with little respect for your particular sensitivities nonetheless? This supposedly honorable creator of installations and performances for other big-city folk, them with similar talents for screwing up their lives flatter than hammered shit and then proclaiming themselves daring and adventuresome all the same? This giant baby prone to shamelessly soiling himself with clocklike precision, every hour on the hour, not only by failing to resist lying down with a faithless wife of another man and failing to resist social drinking with said faithless wife, but also by failing to mention the existence of a younger lady lover whilst in the company of said faithless wife? This unfathomable infant who then whines when he doesn’t get what he wants when he wants it, yet cares not a whit about what his ladyfriend wants and don’t want? This man is a common toad, nothing more or less, from his inability to treat you, his ladyfriend, with some faint semblance of respect and consideration and the like to his inability to make out even the dimmest outlines of good and evil, deeply lacking as he is in the rusty old secondhand moral-compass department. This cocksucker needs to get told to fuck himself, with conviction and with finality, at long last.

Sure, there’s more to parse here, if the hour permits and canned peaches are on offer. We could muse and lament and reconnoiter the ridge, so to speak, offering up various interpretations of them who would sooner cavort and parry with a married woman than honor certain unspoken vows of allegiance to their current lady companions. We could hazard a guess about why a man, long in the tooth as aforementioned cocksucker is, might prefer the company of married women and much-younger gals, them that don’t expect marriage yet (either because they’re already married or they’re too young to push the point), all gals who don’t expect much, really, beyond the self-proclaimed big-city romance of gallivanting around with a cocksucker who without fail prefers to tour his own glorified excretory passages, admiring the view. We could ask ourselves, with rapidly increasing worry and suspense, is this unwieldy cocksucker a cunt-driven near-maniac or stalwart, driven by principle?

Clearly, we could wantonly waste our higher capacities on such overtures to so-called reason indefinitely, but the returns from such exertions would surely be limited, and such pointlessly looping cranial fucking gymnastics would frankly be a waste of energy for a lady of your intelligence. And in candor, our moment permits interest in one question and one question only: Will you be more than a target for ass-fucking? To not grab ankle is to declare yourself interested.

Suffice it to say that simple courtesy might’ve forestalled this event. Say the artist cocksucker in question invited you along the first time said married woman arrived in his nefarious circle. Say the artist cocksucker described you, head to toe, to said faithless ex-lover, repeating his devotion in words that might forestall her brushin’ against his cock repeatedly henceforth. Say the artist cocksucker swore up and down, not prompted or commissioned by your words of urging, that his dalliance with this faithless woman was a lamentable crime against the faithless woman’s husband and the faithless woman’s child, one that should never be repeated and for which he’d already felt untold wells of guilt and sorrow. Say the artist cocksucker wasn’t a fucking cocksucker at all! Personally, I’m waiting to be kept happy by another fucking fairy tale. And I’d rather try touching the moon than take on this artist cocksucker’s thinking. This is man who daily swims through a goddamn quagmire of piss and bullshit and calls it a proud and honorable journey.

His offenses are more numerous than the stars in the firmament, but the most damning among them may be his inability to mention you, his current paramour, to his faithless former (and possibly even current) lover. When paired with his utter lack of remorse for previous unconscionable acts, what we discover is the portrait of a man without a conscience, who dances with whatever whore’ll have him and pays no mind to the last. You may believe the dangers here remote, or believe your anxiety unjustified. Lest your initiative and stick-fucking-to-it-iveness all be in fucking question, mark my words: You could very well waste as much as a decade of your life with this soiled bawling brat who lacks gratitude and common sense and common fucking courtesy. I wish to see you extricated from all these complications and difficulties. Such encumbrances don’t suit you, not yet 30 years of age and, present circumstances notwithstanding, thoughtful and mature beyond your years. Tell this cocksucker to get gone for good, tell him to fuck himself permanently and forever, and go forward and seek men cut from a far finer fucking cloth.

However you accomplish communication with that son of a bitch, do it soon. And once you tell him to get fucked, don’t pick him up from the canvas when he moans, as he’s likely to, and dust him the fuck off. But don’t expect sadness or regret from such as him, either. Even as you dismiss him through tears, he might smile and call it an escape. He might just call it his morning’s entertainment. He is not to be trusted, and not to be tolerated.

Few choices are ours to make, and some might say that others such as myself should stay the fuck out of the process. But I say live free and fuck those who would disagree, and also fuck those who would demean you with ongoing deception and disrespect. Heartbroke though you may be today, sooner than you might guess, your reminiscences of this artist cocksucker will be marked by rollicking laughter, not regret. Some ancient Italian maxim fits our situation whose particulars escape me. I don’t pretend to know the future, and a man’s got to work a few dogs to know how the world wags its tail. But elderly, faithless, bought-out, self-serving, lying sons of bitches would be well-advised to get fucked, and them as heals under my care stay fucking healed. Those that doubt me suck cock by choice!


Got a question for Polly? Email Her advice column will appear here every Wednesday.

All letters to become the property of Ask Polly and New York Media LLC and will be edited for length, clarity, and grammatical correctness.

(Click here to subscribe to the Ask Polly RSS feed.)

Order the new Ask Polly book, How To Be A Person in the World, here. Got a question for Polly? Email Her advice column will appear here every Wednesday.

Get Ask Polly delivered weekly.

By submitting your email, you agree to our Terms and Privacy Policy.
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

All letters to become the property of Ask Polly and New York Media LLC and will be edited for length, clarity, and grammatical correctness.

Ask Polly: Is My Boyfriend Bad News?