Ask Marlowe

Ask Philip Marlowe, street savvy PI

“He solves hearts like he solves murders — cynically, and with a double scotch.”

Dear Marlowe,

I’m a 37-year-old secretary who’s been in love with my boss for three years. He’s charming, successful and smells like expensive aftershave gargled with subtle emotional unavailability. But last week I saw him having lunch with a younger woman who looked like a perfume ad with legs. Should I tell him how I feel? Or just buy a dozen cats now and start naming them after characters from Pride and Prejudice?

— Hopeless in Hamilton

Dear Hopeless,

Dollface, I’ve seen this one before. You’re the type who stares at a guy like he’s the last pack of cigarettes in a blackout. He notices — but only when his usual brand runs dry.

This boss of yours? He’s the kind of man who keeps a bottle of bourbon in his desk and a woman’s heart in every town from Eyebrow to Dildo. You say he’s charming? So is a loaded .38 in the wrong hands. And a guy who smells like he bathes in regret and cologne usually leaves more broken hearts than unpaid bar tabs.

Here’s what you do: take those three years of pining, light ’em up like a cheap cigar, and toss ’em in the ashtray. Buy a new dress, not a dozen cats. Walk into that office like you own the building, and when he says something slick, smile like you’ve got a secret and tell him he’s yesterday’s newspaper.

Love doesn’t wear pinstripes, sweetheart — it wears scars. And you’re better off collecting your own than polishing his.

Stay tough,

Marlowe

Dear Marlowe,

My husband won’t stop talking about his ex-wife. Every dinner turns into a history lesson in her faults, her lasagna or her legs. I’m beginning to think I’m just a rebound with better meatloaf. What should I do?

— Second-Hand Wife in Saskatoon

Dear Second-Hand,

You ever buy a used car, sweetheart? One that looked shiny on the lot, but once you turned the key it made a sound like a dying saxophone and reeked of disappointment? That’s your husband.

Men like him keep their exes in their back pocket like a detective keeps an old case file— dog-eared, bitter, and never quite closed.

You’re not his rebound, sugar. You’re the evidence he’s still stuck in the courtroom of her memory. And all you’re doing is serving time. Next time he starts talking about her lasagna, throw the meatloaf at his head. Then remind him the past belongs in the morgue, not at the dinner table.

And if he doesn’t get the message, walk out the door with your recipe book and your dignity. There’s always a barstool, a jazz tune and a better man waiting somewhere.

Heartbreak doesn’t come with a safety,

Marlowe

Dear Marlowe,

I think my girlfriend is cheating on me with her personal trainer. She says they’re just “sweat buddies,” but I’ve seen the way she smiles when he calls her Tiger. Should I confront her? Or should I join the gym and watch the betrayal in real time?

— Bench-Pressed in Burlington

Dear Bench-Pressed,

If a dame starts calling her personal trainer Tony the Glute Whisperer and suddenly your bedroom feels colder than a corpse in January, you’re not paranoid — you’re just reading the signs like a man who finally learned how to sound out deceit.

You’ve got two options: the high road, or the highway. If you confront her, don’t whimper — grit your teeth and ask straight. If she blinks, fidgets or answers with a question like “Why don’t you trust me?”, congratulations — you’re sleeping with the enema.

And if you join the gym? Bring brass knuckles and a protein shake. Because nothing’s worse than watching another guy spot your girl on squats while you’re choking on kale and jealousy.

But I’ll tell you this for free: when someone starts working out just to feel more single, the relationship’s already on life support. Pull the plug and walk out before she gives you a protein-packed heartbreak smoothie.

Keep your chin up and your dumbbells down,

Marlowe

Dear Marlowe,

My ex keeps texting me “just to check in.” He says he’s “happy” with his new girlfriend, but somehow he still finds time to send me nostalgic playlists and “remember when” messages. Am I being played, or does he secretly want me back?

— Still Typing Back in Toronto

Dear Still Typing,

Ah, the ol’ “just checking in” routine. Classic move from a man whose ego can’t fit in a carry-on.

Listen, sweetheart — if he’s really happy, he wouldn’t be haunting your inbox like a ghost in a cologne ad. He doesn’t want you back; he wants you on the hook. You’re not a woman to him — you’re a mirror. And when he texts you, he’s not saying “I miss you.” He’s saying “Remind me I’m still desirable.”

You’re not being played. You’re being kept. Like a vinyl record he never listens to but refuses to throw away. Don’t respond. Don’t engage. Block him like a bad number and pour yourself a drink.

The past belongs in noir novels and unsolved cases — not in your DMs.

Case closed, Marlowe

Dear Marlowe,

You’ve heard the rumours about me. The ones that say I’m bad news, a heartbreaker, a thief of men’s wallets and souls. They’ve got it all wrong. I don’t break hearts, darling — I collect them.

My current target? A charming little lawyer who thinks he’s got it all figured out. I’ve been feeding him sweet lies and watching him eat them like candy. But lately, he’s been asking questions — too many questions. So, what do you think? Should I silence his curiosity, or do I let him see what happens when he pokes the beast?

You’d be wise to keep your distance. But if you insist on helping me, meet me at the pier at midnight. I’ll be the one with the smile that could kill.

— Yours in mischief, Vera Malone

Dear Vera,

Oh, Vera, sweetheart, you’re a handful and a half, aren’t you? But that’s the problem with dames like you — always stirring the pot, never worried about who’s going to spill it. You’ve got that look in your eyes, the one that says you could pull off a heist and a heartbreak before breakfast. I respect that.

But here’s the thing, doll — curiosity killed the cat, sure, but satisfaction brought it back. So what are you gonna do when your lawyer friend realizes the game isn’t a game any more? You gonna spin him another lie, or are you gonna let him see the truth before he falls in too deep? Dames like you don’t wear diamonds, doll — they wear secrets.

You’ve got two choices: keep playing your hand and let him unravel you, or keep him guessing long enough that he never figures out the trap. Either way, someone’s getting burned, and I’m guessing it won’t be you. But remember, Vera — if you keep running, sooner or later, someone’s gonna catch you.

I’ll be at the bar when you make up your mind.

Shaken and stirred, Marlowe

Dear Marlowe,

I don’t trust the COVID vaccine. I’ve read that it alters your DNA and that it was rushed out too quickly. Big Pharma’s making a killing, and we’re just the guinea pigs. I haven’t gotten it, and I don’t plan to. What do you think?

— Skeptical in Saint-Jean-sur-Richelieu

Dear Skeptical,

Listen, babe, I’ve tangoed with more shady characters than a poker game in a storm drain, and lemme tell ya — if anyone was gonna inject me with something dodgy, it’d be the kind of dame who wears heels sharper than her intentions. But the vaccine? That ain’t the con you’re looking for. It’s the real McCoy. It won’t turn your genes into alphabet soup or make your blood magnetic. It will, however, keep you from breathing through a garden hose in the ICU.

So unless your idea of fun is learning what a ventilator tastes like, roll up that sleeve and take your medicine like a grown-up. This ain’t 1947 — modern science isn’t trying to kill you. It’s just trying to keep you alive long enough to pay your taxes.

Wake up and smell the malarkey, Marlowe

Dear Marlowe,

Why are we putting fluoride in the water? I didn’t vote for this. I don’t need the government mass-medicating me through my tap. What’s next, Prozac in the coffee?

— Parched Patriot

Dear Parched,

Kid, I’ve had enough cheap bourbon to know what something tastes like when it’s trying to kill me. And fluoridated water? That’s not poison — it’s just science’s way of telling your teeth, “Hey, maybe don’t rot out of your skull before you’re forty.”

If you think the government’s biggest offence is giving you marginally better molars, you’ve clearly never dealt with the zoning board. You want clean, flavourless, cavity-resistant water? That’s not tyranny. That’s a public service.

Quit chewing on conspiracy and brush up on reality, Marlowe

Dear Marlowe,

Is it just me, or is everything connected? The deep state, adrenochrome harvesting, pizza parlours with basements that don’t exist … Q has revealed the truth, and the truth is terrifying!

— Red-Pilled and Ready

Dear Red,

The only thing terrifying here is how deep you’ve gone into the rabbit hole and come out clutching a handful of breadcrumbs labelled “Wake Up, Sheeple.”

I’ve followed trails that led through Chinatown opium dens, backroom baccarat tables, and even a rogue mime collective in Chibougamau. But even I couldn’t chart the corkboard-and-string nonsense you just laid out. And if only it were just you who thinks this way.

There is no shadow cabal, no secret blood smoothies, and no pizzagate basement — trust me, I checked. You’re chasing ghosts in a funhouse, kid, and the only thing real is the mirror showing you a face that’s forgotten how to blink.

So put your lips together ... and blow, Marlowe

Dear Marlowe, I’m a, ahenh, “public servant” of some renown, and I recently received a rather generous gift — a $400 million private jet — from a foreign nation with which I have excellent personal and diplomatic relationships. Now, suddenly everyone’s clutching their pearls and yammering about “ethics” and “conflicts of interest.” I don’t see the problem. Can’t a man accept a nice gesture — a gift free of charge — without it being blown out of proportion? I could be stupid and say no. But why would I?

— Sky-High and Misunderstood

Dear Misunderstood,

Let me break this down for you like a two-bit safecracker at closing time.

If you’re a politician or a public servant, and someone tosses you the keys to a flying palace that costs more than the GDP of several moderately successful island nations, that’s not a “gift.” That’s a favour — and favours, my friend, are just bribes with a bow on ’em.

You can’t call yourself a man of the people while sipping champagne at 40,000 feet in a titanium cigar tube that came courtesy of the Sultan of What’s-It-To-Ya. Ethics isn’t just about what’s legal — it’s about what looks like you might be selling influence faster than hot dogs at a ball game.

You want respect? Try not looking like you’re sponsored by the villain from a Bond movie. The only thing flying higher than your new jet is your detachment from reality.

Next time someone offers you a $400-million token of friendship, try saying, “No thanks — I’ve already got a bike.” And anyway, what if the president found out?

— Trojan Horse Associates, Marlowe

Got a question, a broken heart, or a theory that smells like damp trench coats and gun oil? Send it to retired gumshoe Philip Marlowe. He’ll shoot straight — even if you’re aiming crooked.