Cuffing Season and the Red Flags You Shouldn’t Ignore When Dating Men

Introduction: What Is Cuffing Season?

The air gets colder, the leaves start to fall, and suddenly, even the most commitment-averse men start downloading dating apps again. Welcome to cuffing season — that peculiar time of year, usually autumn through winter, when people rush to “cuff” themselves to a partner for warmth, companionship, and someone to watch six-hour true crime documentaries with.

The term comes from the slang “cuffed,” meaning tied down. Unlike the sweaty, carefree summer of casual flings, cuffing season is about pairing off before the cold, dark months set in. Nobody wants to trudge to the Christmas market alone, and Netflix isn’t quite the same without someone beside you (ideally bringing snacks).

But here’s the catch: desperation makes us overlook the obvious. When it’s cold, dark, and lonely, we’re more likely to excuse questionable behaviour in the hope that it’s just “quirky” instead of concerning. Which is why cuffing season is also the perfect time to remind ourselves of the red flags men wave — often without even realising it.

Because yes, sometimes a man just is bad at laundry. But sometimes, his inability to wash his own socks is symptomatic of something deeper: entitlement, immaturity, or expecting you to mother him.

Let’s take a tour through some of the most common red flags you should watch out for this cuffing season.

Red Flag 1: He Wants to Know Where You Are at All Times

On the surface, this can look like care. He texts, “Did you get home safe?” He asks, “What are you up to today?” And early on, it might feel flattering — like he’s really invested.

But notice the frequency. If “checking in” becomes constant monitoring, that’s not affection, it’s control. Wanting to know your whereabouts 24/7 often signals insecurity at best, and controlling behaviour at worst.

Healthy relationships are built on trust, not surveillance. You shouldn’t feel like you’re reporting to your line manager every time you leave the house. If he insists on access to your location, pressures you to text back immediately, or sulks when you want time alone, it’s not romance — it’s a red flag waving frantically in the cold winter wind.

Red Flag 2: He Doesn’t Do His Own Laundry

It might sound trivial, but stay with me. A man who has reached adulthood without mastering the washing machine isn’t just lacking domestic skills — he’s advertising his expectations. Who, exactly, does he think is going to do it for him?

Often, the answer is his mother. And if he’s transitioning from being looked after by Mum to being looked after by you, congratulations: you’ve not gained a partner, you’ve acquired a dependent.

Laundry represents more than clean clothes. It’s about self-sufficiency, respect for domestic labour, and whether he sees you as an equal or a live-in maid. If he jokes about “not knowing how to fold,” that’s fine. But if he genuinely believes housework is beneath him? That’s not just laziness, it’s sexism dressed up as incompetence.

Red Flag 3: He Speaks Poorly of All His Exes

Yes, breakups are messy. Yes, everyone has a story about someone they dated who turned out to be less than ideal. But if every single one of his ex-girlfriends is branded “crazy,” “toxic,” or “a psycho,” pause for thought.

One difficult relationship? Understandable. A pattern of demonising every woman he’s been with? That suggests the common denominator might not be them.

This kind of rhetoric often signals a lack of accountability. Instead of reflecting on his own role in a failed relationship, he paints himself as the eternal victim. It also tells you how he’ll talk about you if things don’t work out.

Red Flag 4: He Never Plans Anything

At first, it seems spontaneous. You say, “What should we do?” and he replies, “Whatever you want.” How sweet, right? Wrong.

A man who never takes initiative — whether it’s planning a date, cooking dinner, or even deciding on a film — is outsourcing the emotional labour of the relationship to you. You become the cruise director of his life, constantly steering while he passively goes along.

Indecision can be charming in small doses, but as a long-term pattern it’s exhausting. Relationships require effort on both sides. If he can’t be bothered to plan a single evening, what else will he avoid responsibility for?

Red Flag 5: He Tries to Rush Intimacy

Cuffing season is prime time for this one. The cold weather, the Christmas vibes, the promise of snuggling under blankets — all of it creates fertile ground for men who want to fast-track intimacy.

If he’s pushing for sleepovers in week one, introducing you to his friends immediately, or already talking about your “future together,” be cautious. Sometimes it’s genuine enthusiasm. Other times it’s “love bombing” — an attempt to sweep you off your feet so quickly that you don’t have time to notice the cracks.

Rushing intimacy skips over the important part of dating: figuring out whether you actually like each other. And cuffing season, with its pressure to couple up, makes it easier to confuse intensity with compatibility.

Red Flag 6: He Doesn’t Respect Your Boundaries

Boundaries are sexy. They’re also non-negotiable. A man who teases you for saying no, pushes you to “just have one more drink,” or ignores the signals you’re not comfortable — that’s not harmless fun, it’s a warning sign.

Respect for your boundaries in small things (like food, time, or texting habits) usually reflects how he’ll handle bigger ones (like sex, family, or finances). If he can’t handle a “no” to a night out, how will he handle a “no” in the bedroom?

Red Flag 7: He Has No Female Friends

This one isn’t always a dealbreaker, but it’s worth examining. A man with zero female friends often either doesn’t respect women as equals, or sees them only as potential partners.

Healthy men have platonic friendships with women. If he dismisses women as “too much drama” or “I just don’t get on with girls,” that’s not a quirk — that’s a worldview. And it usually means he sees women primarily in relation to what they can give him, rather than as full, complex human beings.

Why These Red Flags Matter More in Cuffing Season

Cuffing season amplifies the urge to settle. You’re cold, he’s convenient, and suddenly you’ve excused away the fact that he hasn’t washed his bedsheets since the Jubilee.

But small red flags don’t stay small. The man who “just wants to know where you are” might become the partner who controls your social life. The man who “doesn’t do laundry” might become the partner who expects you to manage the household while he plays Xbox.

Winter relationships can be wonderful — cosy, romantic, grounding. But they should add warmth to your life, not drain it. The trick is remembering that cuffing season is a social trend, not a mandate. You don’t need to accept red flags just because it’s chilly outside.

Conclusion: Don’t Trade Red Flags for Red Roses

Dating is hard enough without seasonal pressure making us ignore our instincts. If something feels off, it probably is. Trust yourself.

Cuffing season can be fun — an excuse for hot chocolate dates, festive markets, and endless sofa snuggles. But don’t confuse convenience with compatibility. The right man won’t need constant check-ins, expect you to do his laundry, or sneer at his exes. He’ll respect your time, your space, and your boundaries.

So as the nights draw in and dating apps start buzzing again, remember: red flags aren’t decorations. They’re warnings. And if he’s waving one? Put down the mulled wine, pick up your coat, and leave him cuffed to his own immaturity.