A Toronto Edition Guide to Holiday Gifting in the Undefined Era
In the Words of MyCheekyDate — Toronto
Because nothing says modern romance like wandering through a mid-December Indigo at Yonge & Eglinton wondering whether buying someone a candle counts as emotional intimacy in this economy.
Ah, the holidays in Toronto.
A season of twinkle lights at the Distillery Market, hot cocoa on Queen West, and the sudden realization that you have absolutely no idea what to buy the person you’re kinda-sorta-maybe-possibly dating.
You know them.
You like them.
You’ve had a few really good dates — maybe even braved the TTC together, which is practically a bonding ritual —
but you’re not quite at the “Here’s a gift that implies a future condo in Liberty Village” stage.
And so begins…
The Toronto Holiday Gift Anxiety Spiral™.
Let’s unpack it — cheekily, compassionately, and with a nod to the universal truth:
no one has ever defined a relationship by giving someone a box of Purdy’s chocolates.
🎄 1. The Pre-Title Panic (AKA: “What Are We?” Season — Toronto Edition)
Toronto has a very specific kind of early-dating fog:
You’re together enough that ignoring the holidays would feel weird,
but not together enough to buy something that suggests joint hydro bills.
So you stand there in a Kensington boutique holding a mug that says “World’s Okayest Person”,
wondering if it’s ironic, adorable, or a cry for help.
A book?
Cute. Smart.
But books in Toronto can be dangerous — people judge your taste harder than they judge your winter boots.
A sweater?
Relax. You’re not moving to Roncy and adopting a dog together.
A candle?
Intimate… unless it’s from Winners. Winners candles carry zero implied commitment.
Welcome to early dating in the Six.
🎁 2. The Seinfeld Lesson, Toronto Style: Cash Is Not a Love Language
Let us revisit Jerry’s iconic blunder: handing Elaine $182 in cash.
Toronto equivalent?
Sliding someone an Interac e-transfer with the message “Happy Holidays!! 😊”
Bold.
Chaotic.
Legally trackable.
The gift doesn’t have to be big.
It just has to say:
“I notice you, but I’m not trying to meet your parents at a Leafs game.”
🎁 3. The Perfect Lane: Simple, Personal, Under $40, Low-Risk, High-Charm
Here’s the Toronto-approved formula:
Thoughtful but not intense.
Useful but not “I saw this and thought of our future home.”
Personal but not “let me read you my diary.”
CheekyToronto-approved ideas:
✔️ A cozy pair of socks from Roots
Toronto’s unofficial seasonal uniform.
✔️ A small plant from a Queen West shop
Symbolism: “This is cute,” not “Let’s grow together.”
✔️ A fancy hot chocolate mix from SOMA
Festive, local, delicious, zero pressure.
✔️ A TTC token magnet or quirky Toronto-themed gift
Cute, funny, slightly self-deprecating. Peak Toronto.
✔️ A book they mentioned once
Very “I listen,” not “Let’s vacation together.”
✔️ A candle that doesn’t smell like “Musk of Commitment”
Neutral vibes only.
💭 4. The REAL Gift: Clarity Without Clinging
A small, thoughtful gift shows emotional intelligence — Toronto’s hottest winter accessory.
It leaves the other person free to respond however they’d like:
A small gift back → Balanced energy.
A bigger gift → Oh? Bold.
No gift → Valuable seasonal data.
Either way?
You didn’t hand them $182 or a candle called “Lover’s Ember.”
🎁 5. When In Doubt? Light, Thoughtful, Festive Energy Only
Here’s the rule:
If the gift needs an explanation, it’s too much.
If it doesn’t, it’s perfect.
It’s the early-dating equivalent of holding the streetcar door —
kind, thoughtful, and easy to interpret however feels comfortable.
And who knows…
Your small, Toronto-chic gift might just lead to second dates,
shared streetcar rides,
and maybe even a “we survived winter together” moment.
Happy gifting, you cozy legend. 🍁