The Ultimate Guide: How MyCheekyDate Speed Dating Works (Video Tutorial)

In the Words of MyCheekyDate

At MyCheekyDate, we blend low-key sophistication with cheeky charm — a UK-Style approach to modern dating where kindness is the ultimate currency.

Our gatherings are relaxed yet refined, designed for daters who value genuine connection over gimmicks. No name tags, no whistles — just good company, great conversation, and maybe a spark or two.

This short video walks you through how our events work — from booking your seat to receiving your Date-Mates.

🎬 Watch the Video

Prefer to read instead? The full five-step process is outlined below.)

💫 Step-by-Step: The MyCheekyDate Experience

Step 1 — Booking & Confirmation

Reserve your place online through Eventbrite or our website.
You’ll get an instant confirmation email — no paper ticket needed. Just bring your lovely self (and your ID).

Step 2 — Check-In & Mingling

Arrive about 15 minutes early. Our friendly host will greet you, help you settle with a drink, and walk you through the evening — no rush, no pressure.

Step 3 — The Rotation (6-Minute Chats)

Enjoy a series of six-to-seven-minute mini-dates.
Ladies remain seated while gents rotate — quick enough for sparks, long enough for a smile.
No timers, no chimes — just smooth, host-led transitions.

Step 4 — Using the Smart-Card

Log into your digital MyCheekyDate Smart-Card on mobile or desktop (no app required).
Discreetly mark “Yes” or “No” for each guest you meet — paper scorecards are so 2010.

Step 5 — Your Date-Mates

Matches are mutual. By the next day, you’ll receive your Date-Mates email with first names and email addresses of everyone you both selected “Yes.”

💛 The Cheeky Difference: Where Lovely Meets Value

We reward kindness. Guests who bring warmth, wit, and good energy often receive complimentary invitations or blind-date matchmaking opportunities — simply because being lovely never goes out of style.

Our spaces are intimate and refined — think private-club ambiance, soft lighting, and effortless conversation. It’s where authentic meets elegant, and where one night can open the door to many more.

💬 In-Person Speed Dating FAQ

What is MyCheekyDate & UK Style?
MyCheekyDate is American speed dating with a British twist — relaxed, comfortable, and genuinely fun. We celebrate lovely daters who lead with kindness and good energy and reward them with complimentary invitations and discounts.

What type of people can I expect to meet?
Expect a crowd that’s confident, amusing, and a bit cheeky — people who set trends rather than follow them.

How do I reserve my place?
Simply select your city from our homepage, view upcoming events, and register online — no paper tickets required.

Do you screen your daters?
Much like a private club, not every dater is for us. We look for kind, considerate people who treat others with respect. Anyone rude or disruptive may be declined future attendance.

How do I get invited to complimentary events?
By being your delightful self. We notice warmth and kindness — and those who stand out often receive complimentary invitations or blind-date matchmaking at no cost.

How long does a MyCheekyDate event last?
About two hours, including a short intermission to refresh and mingle.

Are there name tags or whistles?
Never. Our events are UK Style — elegant, low-key, and free of gimmicks.

What is a MyCheekyDate ‘Date-Mate’?
A Date-Mate means you’ve made a match! Submit your Smart-Card choices by midnight, then log back in to see who you’ve mutually matched with.

✨ The Takeaway

At MyCheekyDate, we don’t just host events — we create an experience.
With British sensibility, boutique venues, and a dash of cheek, we make meeting someone special feel effortless and authentic.

Ready to see for yourself?

➡️ Find Your City’s Upcoming Events
➡️ Visit Our Full FAQ Page

📝Cheeky Thoughts: Breadcrumbing - The Diet Plan No One Asked For”

In the Words of MyCheekyDate

You know that feeling when he disappears for days… then suddenly sends a “miss your face 😘” text just as you’ve finally moved on?

That, my friend, is breadcrumbing — the emotional version of being handed one crouton when you ordered the full Caesar.

💫 The Push–Pull Rollercoaster

Breadcrumbing thrives on the adrenaline rush.

You get a little hit of attention — a compliment, a like, a random “thinking of you” at 11:47 p.m.” — and boom, dopamine fireworks. You think maybe he’s back!

Then? Silence. Again.

Welcome to the loop: reward, starvation, repeat.

Our brains love it because unpredictability feels like passion.

It’s not. It’s just inconsistency wrapped in cologne and confusion.

😏 The Psychology of the Crumb

Here’s the science — and the sass:

When someone gives us tiny, unpredictable doses of attention, our brains get hooked.

It’s the same system that keeps slot machines profitable and texting habits tragic.

He doesn’t even have to say much — a single heart emoji can send you spiraling into analysis mode:

• Did he mean it?
• Is he warming up again?
• Should I reply?

💡 Cheeky Tip: Don’t. He’s not feeding romance — he’s feeding pigeons.

🧘‍♀️ How to Handle It — The Cheeky Way

When you spot breadcrumbing:

See it for what it is.
It’s not romance — it’s recycled attention. He’s not pursuing you; he’s keeping his options limber.

Don’t feed the birds.
No response is a response. Let him wonder why his “hey stranger” didn’t earn a standing ovation.

Reclaim the chase.
Channel that adrenaline into yourself. Go flirt with life — not the ghost of text threads past.

Upgrade your menu.
You deserve the full five-course meal:

• Consistent attention
• Genuine curiosity
• The sweet stability of someone who actually shows up

🥂 The Cheeky Takeaway

Breadcrumbing is emotional junk food.

It feels satisfying for about thirty seconds, then leaves you overthinking and undernourished.

So next time a man drops crumbs, don’t crawl — crunch.

Wipe your hands, fix your lipstick, and go where the whole loaf is served warm — with effort, humor, and a little cheek.

Because at MyCheekyDate, we don’t settle for morsels.

We host the feast. 💋

Inside Our Venues: Why “Low-Key Sophistication” Leads to Higher-Quality Connections

Step inside any MyCheekyDate event, and you’ll notice something right away — it’s never in a blindingly bright chain restaurant or a noisy nightclub. Instead, it’s that perfectly lit cocktail lounge tucked behind velvet curtains, or the cozy corner of a boutique hotel bar where conversation hums just above the music.

That’s not by chance — it’s by design.

🌿 The Art of the Setting

We’ve always believed that a good venue should whisper quality, not shout it.
Our spaces — from Whiskey Girl in San Diego to The Botanist in Manchester — are chosen for their relaxed sophistication. Plush seating, warm lighting, a good wine list, and just enough background energy to make things feel alive.

Because when people feel at ease, they open up. When the lighting is soft and the energy balanced, confidence rises naturally. A flattering space has that uncanny ability to make even first-time daters feel like they’ve already been let in on a secret.

🥂 The Science of “Just Right”

There’s a reason why five-minute conversations in the right environment lead to stronger connections than hour-long dinners in the wrong one.
It’s not the time that matters — it’s the tone.

Psychologists call it affective contagion — we mirror the mood of our surroundings.
A space that’s curated, calm, and welcoming actually primes our brains for trust and receptivity. The more comfortable you feel, the more authentic you become — and that authenticity is where sparks begin.

💫 Why “Low-Key” Wins Over “Loud”

High-energy venues may seem exciting, but they rarely let two people see one another.
We want laughter, not shouting; conversation, not competition for attention. That’s why you’ll never find us under strobe lights or next to a DJ booth.

Our daters often tell us they feel an instant shift the moment they walk into one of our events — that they can finally breathe. No name tags, no megaphones, no gimmicks. Just a cheeky glass of something lovely, a table set for two, and the quiet hum of possibilities.

💛 The MyCheekyDate Promise

Every venue we choose is a reflection of our philosophy:
Real connections don’t need flash — they need feeling.

Low-key sophistication isn’t just our aesthetic; it’s our strategy.
Because when you create a space that feels effortless, daters can drop the act, ditch the nerves, and show up as their most genuine selves.

And that’s when the real magic — the cheeky, unforgettable kind — begins.

✨ Fancy a go?
Find an event near you and experience the MyCheekyDate difference — where ambiance meets authenticity, and every seat might just be the one.

📝Cheeky Thoughts:💋 Why Men Don’t Flirt Like They Used To

In the Words of MyCheekyDate
The mystery of the disappearing effort.

Remember when a man would lean in just to whisper something that made your knees feel like linguine? When conversation had pace, not lag time? When you didn’t need to decode a message that just said “hey”?

Ah, the lost art of flirting. Somewhere between read receipts and TikTok thirst traps, it quietly left the building — probably holding hands with chivalry and basic attention spans.

💤 The Extinction of Effort

Today’s man flirts like he’s on battery-saver mode.
The grand gestures? Gone.
The witty banter? Outsourced to memes.
A little mystery? Please — he’s already posted three shirtless selfies before 9 a.m.

It’s not that men can’t flirt.
They just don’t see why they should.
Why craft a clever line when you can drop a fire emoji and call it character development?

😬 Fear of the Flop

To be fair — it’s a tough crowd out there.
One wrong word, one misplaced wink, and you’re the next viral screenshot in someone’s group chat.

So many men now tiptoe so carefully…
they forget to actually step forward.

But here’s the rub:
✨ Charm doesn’t survive in caution tape. ✨
It thrives in confidence, mischief, and a little risk.
We don’t want perfect. We want present.

📱 Swipe Fatigue & the Death of Chase

Dating apps were supposed to make things easier.
Instead, we’ve entered the age of emotional scrolling.
Everyone’s browsing — but no one’s investing.

Flirting used to be about discovery.
The spark of “what if.”
Now it’s more like, “what else?”

And that’s the tragedy:
Somewhere in the convenience, the curiosity disappeared.

🧃 The Softboy Era

Ah yes — the modern “nice guy.”
Emotionally fluent. Into breathwork. Probably in therapy.
But planning a proper date? Absolutely not.

He’ll tell you about his inner child, his journaling routine, and his favourite oat milk latte —
and then ghost you before brunch.

He means well.
He’s just… allergic to momentum.

💥 Bring Back the Banter

Ladies, we might have to demand the return of playful pursuit.

A cheeky line.
A compliment with some backbone.
A question that isn’t “wyd.”

Because effort?
💥 Effort is sexy.
💫 Thoughtfulness is irresistible.
💌 Confidence with humour is practically extinct — and therefore, a total power move.

🥂 The Cheeky Takeaway

Flirting isn’t about manipulation.
It’s not about games.
It’s about chemistry — and the courage to show interest without irony.

Somewhere between the endless apps and endless self-protection,
we lost the thrill of the chase.

So here’s a little MyCheekyDate challenge:
Next time you’re tempted to drop a lazy emoji…
Say something actually interesting.
Give someone butterflies again.

Romance might be on life support —
but a little cheek never killed anyone.

📝 Cheeky Thoughts: When Is the “Right Time”? The Truth About Timing and Intimacy

In the Words of MyCheekyDate

Let’s talk about the really uncomfortable thing — when to ‘get it on’.

When is the right time? It’s the most uncomfortable topic, yet it’s also one of the most asked questions we hear from daters.
How soon should I?
When is too soon? When is too long? Should I give in? Should I make the other person wait? Should we hold on to beliefs?

💬 The Honest Truth

There really is no answer to it, you know.

The thing that we at MyCheekyDate acknowledge is this: every person is different, and every feeling is different. There’s no statistic that says that those who wait tend to have more success, or that those who don’t wait have less success.

It can really be just a matter of the two people.

Oftentimes, people who rush into sex can be married together for 30 years. And oftentimes, those who wait for just the right moment at just the right time can see relationships suddenly collapse at a moment’s notice.

We don’t really believe it necessarily has a bearing on much of anything.

💛 The Real Answer

It truly comes down to this: if you feel it — you feel the trust, you feel the connection — and you feel the time is right, then that’s the answer.

But we shouldn’t get caught up in what other people think, in what the world thinks, or in stereotypical ideas about how it “should” be.

It really, truly is about what you believe, not what everyone else tells you to believe.

🌹 No Shame, No Stigma

There should be no shame, no stigma, and no judgment about when two people choose to become intimate.

Whether it’s on the first date or months down the line — both choices are valid. Life is far too short to overthink, overanalyze, or overhype something that should feel natural and human.

If it feels right from the get-go — go for it.
And if it feels right to wait — that’s just as right.

As for anyone who thinks less of you for either choice? Congratulations — you’ve just weeded out someone who isn’t right for you.

Connection is built on respect, trust, and honesty — not timing.

💖 What We Believe

At MyCheekyDate, we’ve watched thousands of daters find connection — some quickly, some slowly — and what stands out most isn’t when something happens, but why.

When two people share mutual respect, trust, and genuine attraction, that’s the real foundation of intimacy.
Not timing. Not rules. Not what anyone else says you “should” do.

Finding Love: Why There’s No “Normal” Timeline (And Why That’s Okay)

In the Words of MyCheekyDate

In the world of modern dating, one of the most common questions daters ask is:
“How long should it take to find someone?”

After months — or even a year — of meeting people, going on dates, and still not finding that one meaningful connection, it’s natural for a bit of doubt to creep in.
“Am I doing this right?”
“Should I have found someone by now?”

The truth is, there’s no universal stopwatch on love.
Every person’s journey is different, and every relationship timeline is unique.

When we start putting ourselves on a dating clock — believing we need to meet someone “within six months” or “by the end of the year” — we often rob ourselves of the very thing that makes dating magical: spontaneity.

It turns what could be an organic experience into a pressure-driven deadline.
And love doesn’t thrive under pressure.

🚧 The Pitfalls of Rushing the Dating Timeline

When daters become fixated on timelines, they can miss the natural flow of connection.
Love isn’t a checklist or a productivity metric.
There are no guaranteed milestones. No fixed deliverables.

Real relationships unfold in their own time.
Sometimes slowly. Sometimes all at once.

By letting go of artificial expectations, daters open themselves up to genuine chemistry — moments that don’t always arrive on schedule, but often arrive when you’re relaxed, curious, and open.

🛤️ Everyone’s Relationship Journey Is Different

Some people meet their person on the second date.
Others? The forty-second.

There’s no correct pace. There’s no ideal window.

What matters most is finding a connection that feels right — not one that fits someone else’s timeline.

Your relationship journey is just that — yours.
Comparison only creates doubt, and doubt creates friction in a process that should be joyful.

🌟 Focus on the Process, Not the Deadline

Instead of asking:
“How long should this take?”
Ask:
“How can I enjoy this more?”
“How can I show up as my most open, relaxed self?”

Think of dating as an adventure, not a race.
You’re not late. You’re not behind.
You’re exactly where you’re meant to be.

When you release the pressure of the stopwatch, something beautiful happens:
you create space.

Space for fun. Space for connection. Space for someone great to walk in — when the time is right.

📝 Cheeky Thoughts: Giving Back with Our “Nights for Suzanne” — Fighting Cancer Together

In the Words of MyCheekyDate

Here at MyCheekyDate, we believe that dating and giving back can go hand in hand. That’s why we created something close to our hearts called “Nights for Suzanne.” It’s a simple yet powerful way for our daters to contribute to the fight against cancer in a way that feels right to them.

We know that people can be skeptical about charities or wonder where their donations go. That’s why we keep it wide open and personal.

All we ask is this: if you’re attending one of our events or purchasing a matchmaking package, simply donate the amount of your ticket or package price to any cancer charity of your choice. That’s right — any charity that you feel connected to in the fight against cancer.

Once you’ve made your donation, just show us that you’ve contributed — and you’re in.
We’ll credit you the amount of your purchase, no matter how big or small.

💛 Making Giving Personal

It’s our way of saying that giving back should be meaningful. Whether it’s a $36 event ticket or a larger matchmaking package, you can turn it into a donation that matters to you. We’ll handle the rest and make sure you’re all set for your dating experience with us.

It’s that simple — and it’s all about joining together to make a difference in the way that feels best for you.

💖 Love, Connection, and Compassion

In the end, it’s not just about finding love — it’s about spreading a little love, too.
And that’s what Nights for Suzanne is all about: coming together as a community, sharing kindness, and doing something that truly matters.

📝 Cheeky Thoughts: Love Isn’t Measured in Dollars — It’s Measured in Drive

In the Words of MyCheekyDate

One thing we often hear from daters is a question about how much a person should make in a year — as if love came with a minimum salary requirement.

But as we watch so many layoffs unfold across industries, it saddens us to think that some daters have set a predetermined income minimum for a potential partner. Because the truth is, that number can change at any time. You could have an amazing job one day and face a layoff the next.

In today’s world, that seems like an awful thing to build a relationship around.

💛 The Ladder of Success Is Always Moving

At MyCheekyDate, we believe that the ladder one is on at any given time is not necessarily where they’ll end up. The ladder of success is just that — a ladder.
Many people who are climbing are on their way up, and many who appear at the top may someday find themselves stepping down through circumstances beyond their control.

It’s all part of life’s natural ebb and flow.

💬 What Really Matters

We believe that ambition, goals, and drive — not current income — are the real markers of potential and partnership. Those are the qualities that never fluctuate with the market. They can’t be laid off, outsourced, or downsized.

When someone has the determination to move forward, no matter where they are right now, that’s what creates success — and that’s what builds lasting relationships.

💖 Love Runs Deeper

At the end of the day, it isn’t about a dollar, or what someone earns today, or might lose tomorrow.
It’s about something far more lasting — the energy, perseverance, and inner strength that define who a person truly is.

Ambition endures. Drive endures. Love endures.

And those are the things that make a partnership strong — not what’s in a paycheck, but what’s in a person’s heart.

📝 Cheeky Thoughts: Beating the Dating Blues — How to Wipe the Slate Clean and Start Fresh

In the Words of MyCheekyDate

Let’s be real: it’s tough out there right now. The economy’s doing somersaults, your favorite spots might be disappearing, and every time you open a dating app, it feels like you’re scrolling through an endless sea of faces. It’s easy to start feeling cynical or to wonder if you’ll ever get to that happy place you see other couples enjoying.

But here at MyCheekyDate, we’re all about helping you wipe that slate clean and start fresh — because every new date is a new beginning.

💛 Wipe the Slate Clean

Think of it like a chalkboard: no matter what’s happened before, you get to erase it and write something new. Maybe you’ve had a rough patch with an ex, or you’re dealing with job stress or financial worries. All of that is real, and it’s understandable that it weighs on you.

But dating is your chance to step into something fresh and embrace the unknown. It’s about pushing yourself a little out of your comfort zone, trying new things — and giving yourself permission to start over each day.

💬 Don’t Let the Past Shape the Present

Don’t let past disappointments or fears shape your future. Instead, try to approach each new connection with an open mind. Don’t ask the next person to fix what the last one didn’t, and don’t carry yesterday’s baggage into today’s possibilities.

Every time you meet someone new, you have a chance to rewrite your story. And who knows? That fresh start might lead to something wonderful.

💖 The Cheeky Perspective

So go ahead — clean that slate, step out there, and give yourself the chance to be surprised. After all, the best connections happen when you’re open to the adventure.

📝 Cheeky Thoughts: What Is the Cheeky Promise? Our Foundation of Kindness and Understanding

In the Words of MyCheekyDate

Let’s talk about the heart and soul of everything we do: the Cheeky Promise.
It’s not just a tagline — it’s the foundation of who we are and how we approach dating. In a world where so many dating companies are rigid and unforgiving, we believe in something different: kindness, understanding, and a truly human connection.

We know life happens. Sometimes daters need to reschedule last minute, or they’re dealing with things that are out of their control. Instead of saying, “Sorry, your ticket’s gone, tough luck,” we choose to be understanding. We’d rather let someone choose any future event that works for their schedule than add stress to their day.

Sure, this might mean we have to occasionally reschedule or shift events around — and we totally get that it can be frustrating for those who were really looking forward to a particular date. But that’s the trade-off we’re willing to make, because at the end of the day, our ethos is all about kindness.

💛 Rewarding Our Loveliest Daters

And here’s the best part: we actually reward those who embody that same kind and understanding spirit.
Our loveliest daters — the ones who show up with a great attitude and treat others with warmth — are the ones who get invited back for complimentary events, included in our blind-date matchmaking program at no additional cost, and even receive personal advice from our team.

It’s our way of saying thank you for being the kind of person who makes our events special.

🧭 Policies With a Human Touch

Our Policies & Guest Experience and Refunds & Cancellations pages reflect the same promise: a commitment to fairness, flexibility, and understanding.
We’d rather work with guests to find solutions than hide behind rigid terms — because compassion creates better experiences for everyone.

💖 The Heart of It

In other words, the Cheeky Promise is simple:
Be kind. Be understanding. And we’ll do everything we can to make your dating experience amazing.

Those who don’t get it? Well, they just don’t thrive here — and that’s okay. Because at MyCheekyDate, we believe that kindness is the real key to finding lasting connections.

That’s the Cheeky Promise.

📝 Cheeky Thoughts: The Dreadful Reality of Ghosting — Why We Believe in Better Dating Etiquette

In the Words of MyCheekyDate

👻 Boo! It’s spooky season — but there’s one kind of ghost we could all do without: the dating kind.
At MyCheekyDate, we’ve hosted over 25,000 events across 65+ cities, and while we love a little mystery, we can’t stand a disappearing act.

Ghosting has become one of modern dating’s worst habits — and we get it, life gets busy. But vanishing without a word? That’s a move scarier than any haunted house.

💫 Why Ghosting Haunts More Than Just the Inbox

We’ve heard it all:

“They were great, then poof!—gone.”
“Did I say something wrong?”
“Are they okay? Should I check the hospitals?”

Sound familiar? Ghosting doesn’t just leave someone wondering what happened — it chips away at confidence and connection. Whether it’s after one date or a few months, it’s never fun to feel like someone’s turned into a ghost in your messages.

And let’s be honest: modern dating already has enough plot twists without adding a paranormal one.

💞 The Cheeky Fix: Kindness Over Silence

We believe great dating etiquette is simple: just be honest.
You don’t have to write an essay — sometimes a message like “You’re lovely, but I didn’t feel the spark” is all it takes. It’s kind, direct, and leaves everyone free to move on with dignity.

At MyCheekyDate, our Cheeky Promise is built on empathy and understanding. We see time and again that kindness creates better connections — whether at an event, on a follow-up date, or even when parting ways.

🌹 Our Cheeky Takeaway

Dating should be exciting — not haunting. 👻
So next time you feel like disappearing, don’t. Send a short, kind note instead. You’ll be surprised how far simple courtesy can go.

Because at MyCheekyDate, we’re all about creating real connections — not ghost stories.

📝 Cheeky Thoughts: Fun and Affordable First Date Ideas — Because It’s Hard Out There!

In the Words of MyCheekyDate

Let’s face it, dating can be a bit of a rollercoaster—and sometimes, that rollercoaster comes with a hefty price tag. But here at MyCheekyDate, we believe you don’t need to break the bank to have a fabulous first date. In fact, some of the best dates are the ones that are a little creative, a little quirky, and totally “cheeky.”

So, let’s talk about some fun, affordable first date ideas that are uniquely us. No fancy restaurants or over-the-top extravagances—just good vibes and great connections.

💡 Cheeky Date Idea #1: Art Walk Adventures

If you’re in a city like Houston or Los Angeles, check out a local art walk or gallery night. It’s often free or low-cost and gives you a chance to wander through colorful exhibits and chat about your favorite pieces. Plus, it’s a great way to spark conversation without the pressure of a formal dinner.

💡 Cheeky Date Idea #2: Bookstore Browsing

In cities like New York or Boston, a trip to a quirky bookstore can be a charming and low-cost date. Pick out a book for each other, read a few passages, and see where the conversation takes you. It’s a great way to get to know someone’s tastes and have a little literary fun.

💡 Cheeky Date Idea #3: DIY Picnic in the Park

No matter where you are—be it Central Park in New York or the Boston Common—pack a simple picnic and enjoy the great outdoors. Bring along some homemade snacks or grab a few treats from a local deli. It’s laid-back, affordable, and totally charming.

💡 Cheeky Date Idea #4: Local Trivia Night

Head to a local pub for trivia night! It’s a fun and interactive way to team up and get to know each other without spending a lot. Plus, you get to show off your random knowledge and share a few laughs along the way.

📝 Cheeky Thoughts: Great First Date Spots in Boston — Our Cheeky Picks for Chemistry and Charm

In the Words of MyCheekyDate

Welcome to the Boston edition of Cheeky Thoughts! We know that finding the perfect first date spot can make all the difference. Whether you’re wandering through historic neighborhoods or enjoying a trendy new venue, we’ve got you covered with some of our favorite Boston locales.

🏙️ Back Bay

1. Oak Long Bar + Kitchen — Nestled in the historic Fairmont Copley Plaza, this elegant spot is perfect for a classy, laid-back first date. Enjoy craft cocktails and a warm, inviting ambiance that’s perfect for easy conversation.

2. Newbury Street Café — For a more casual vibe, take a stroll along Newbury Street and stop into one of the cozy cafés. It’s perfect for a relaxed coffee date with plenty of people-watching.

🌊 Seaport District

1. Lookout Rooftop and Bar — With stunning views of the Boston Harbor, this rooftop bar is a fantastic spot to impress your date. Enjoy the breeze off the water and a laid-back vibe that’s perfect for a memorable first meeting.

2. Legal Harborside — For a quintessential Boston experience, head to Legal Harborside. It’s a great spot to share some seafood and enjoy the waterfront setting.

🎨 Cambridge (Harvard Square)

1. The Sinclair — Located in the heart of Harvard Square, The Sinclair offers live music and a cool, laid-back atmosphere. It’s perfect for a date night that’s a little out of the ordinary and full of personality.

2. Tatte Bakery & Café — For a more low-key date, Tatte is a beloved local favorite. Enjoy a pastry and a coffee in a cozy, charming setting that’s perfect for easy conversation.

🌳 South End

1. The Beehive — This bohemian spot in the South End is known for its live jazz and eclectic vibe. It’s a great place for a date that’s full of character and a little bit of adventure.

2. Barcelona Wine Bar — If you’re in the mood for tapas and a laid-back, romantic vibe, Barcelona in the South End is a fantastic choice. Share a few plates and enjoy the cozy ambiance.

📝 Cheeky Thoughts: The Good, The Bad & The Ugly of Dating Who You Really Are (Not Who You Want to Be)

In the Words of MyCheekyDate

Let’s talk about something every single has wrestled with at some point — the idea of finding someone who’s the perfect complement to the person you wish you were.
It sounds romantic, right? But let’s get real: dating isn’t about building a wish list of traits you don’t have — it’s about being brave enough to show up as your authentic self.

At MyCheekyDate, we’ve seen it all — from the dreamers who picture dating someone totally opposite, to the charmers who think opposites always attract. But in reality, when you date based on an idealized version of yourself, it rarely lasts.

💫 The “Wish List” Trap

We see it over and over: someone from a small family dreams of finding a partner with a huge, boisterous one because they never had it.
A quiet introvert seeks out an extrovert to “balance them out.”
A career-driven dater looks for someone spontaneous to help them “relax.”

It’s a nice idea — but here’s the truth: the further your dating choices stray from who you actually are, the more those differences start to clash over time.

A few months or a year later, the very things that drew you in may start to divide you. The “complement” you thought you needed ends up being the mismatch you never saw coming.

❤️ Real Connection Comes from Real You

Authentic relationships are built on comfort, not performance.
When you stop trying to be the “ideal version” of yourself, you create space for genuine connection.

If you’re someone who loves quiet nights in, find someone who enjoys the same.
If you’re spontaneous and outgoing, choose someone who loves that energy.
You don’t need someone to complete you — just someone who matches you.

At MyCheekyDate, we’ve spent nearly two decades watching chemistry unfold — and the best matches happen when people stop trying to impress and start trying to connect.

🌹 Our Cheeky Takeaway

Date from who you are, not who you’re trying to be.
Because the spark that lasts doesn’t come from pretending to be perfect — it comes from being perfectly you.

So embrace your quirks, lean into your energy, and find someone who fits your rhythm.
That’s not just compatibility — that’s real connection.

Cheeky Thoughts: So You’ve Matched at MyCheekyDate — What Happens Next?

In the Words of MyCheekyDate

So, you did it! You came to one of our MyCheekyDate speed dating events, had a fantastic time, and voilà — you’ve got a match. Now what? Well, that’s where the fun really begins. Here’s your guide to keeping things just as cheeky, confident, and connected after the event as they were during it.

After your event, you’ll head over to your MyCheekyDate dashboard and mark the names of the people you’d love to see again. If the feeling’s mutual, you’ll get that magical “It’s a match!” notification. You’ll receive their first name and email, and then it’s your turn to reach out. Keep it light, keep it breezy, and pick up right where you left off.

If you chatted about your mutual love of hiking, espresso martinis, or 90s throwback playlists — start there. A little continuity goes a long way in making your first post-event message feel natural and genuine.

💌 When and How to Follow Up

There’s no need to rush. Take things at a comfortable pace, just like at our events. Once the conversation flows easily, suggest something simple — a drink, a walk, a cheeky coffee meet-up. Remember, first dates work best when they feel effortless.

Here’s a fun insider tip: many of our daters love going back to the venue where they first met. There’s something nostalgic about revisiting that familiar space — turning a few minutes of speed dating into a full-fledged first date with chemistry already built in.

🌹 From Match to Magic

So go ahead — take that match and turn it into something special. Be yourself, stay kind, and let things unfold naturally. Whether it’s a follow-up coffee or a dinner that lasts three hours longer than expected, the best stories always start the same way: two people willing to show up and see what happens.

At MyCheekyDate, we’re cheering you on every step of the way — because we know that sometimes, all it takes is a few minutes and an open heart to find something truly extraordinary.

📝 Cheeky Thoughts: Great First Date Spots in Los Angeles — Our Cheeky Picks for Chemistry and Charm

In the Words of MyCheekyDate

Welcome to the Los Angeles edition of Cheeky Thoughts! We know that finding the perfect spot for a first date can set the stage for real chemistry, and we’ve got you covered with some of our favorite neighborhoods. Whether you’re downtown sipping cocktails with skyline views, enjoying a cozy corner in Studio City, strolling by the marina in Marina Del Rey, or taking in the beachy breeze in Manhattan Beach — these first date spots in Los Angeles are sure to add a little magic to your evening.

🌆 Downtown Los Angeles

1. Perch — A chic rooftop bar with stunning views of the LA skyline. Perfect for cocktails at sunset, it’s the kind of spot that makes a first date feel effortlessly glamorous — and a bit cheeky.

2. The Last Bookstore — For a more quirky and laid-back vibe, this iconic bookstore is a great place to wander through aisles of books and spark easy conversation. It’s a low-pressure way to connect while sharing a few laughs over unexpected finds.

🎬 Studio City / Sherman Oaks

3. Firefly — A romantic hideaway in Studio City with a gorgeous garden patio. It’s intimate and atmospheric — perfect for a first date that feels cozy and memorable.

4. The One Up — If you want something a little more playful, this arcade bar in Sherman Oaks is perfect. It’s casual, fun, and a great way to break the ice with a little friendly competition (and maybe a rematch date).

🌊 Marina Del Rey

5. Cast & Plow — Overlooking the marina, this spot at The Ritz-Carlton offers a sophisticated yet relaxed setting. It’s perfect for enjoying a sunset cocktail and watching the boats drift by.

6. Salt Restaurant & Bar — Located right on the waterfront, Salt offers breezy coastal vibes that make it perfect for a laid-back first date. Share a few small plates, take in the view, and enjoy the easy rhythm of marina life.

🏖️ Manhattan Beach

7. The Strand House — With its stunning ocean views, The Strand House is a top pick for a first date. It’s elegant but not stuffy — ideal for great conversation and that golden-hour glow.

8. Manhattan Beach Creamery — For something lighthearted, head to this charming ice cream shop. Grab a cone, take a stroll along the beach, and let the evening feel as effortless as it should.

💞 Our Cheeky Takeaway

At the end of the day, the best first date spots in Los Angeles are the ones that help you relax, laugh, and connect. Whether you prefer rooftops or beaches, the secret ingredient isn’t the venue — it’s the energy you bring to it.

Because as we’ve learned from hosting thousands of MyCheekyDate events across 65+ cities, real chemistry doesn’t come from the menu — it comes from the moment.

📝 Cheeky Thoughts: “Who Pays on a First Date? Our Cheeky Take on Chivalry and Chemistry”

In the Words of MyCheekyDate

All right, let’s dive into that age-old dating question that never fails to spark a lively debate: who pays on the first date?
We’ve heard every opinion imaginable — on Instagram, at our events, and from our lovely daters around the world. And yes, this topic always gets people talking! But here’s our cheeky take, and it might surprise you.

At MyCheekyDate, we absolutely adore chivalry. There’s something timeless and genuine about someone wanting to treat their date to a nice dinner or drinks. It’s a beautiful gesture — one that speaks to kindness and confidence.
But — and here’s the twist — we believe chivalry means even more after you’ve made a genuine connection.

💫 Real Chemistry Comes Before the Cheque

Imagine this: you meet someone at one of our MyCheekyDate speed dating events, you share an effortless chat, and the conversation just clicks.
That’s where authentic chemistry begins — and where true chivalry can follow naturally.

It’s not about grand gestures right off the bat. It’s about showing genuine interest after you’ve discovered a real spark. Many of our guests tell us they prefer to start simple — maybe just a drink or a coffee — and let things grow naturally from there.

The truth is, no one wants to feel obligated on a first date. The best connections happen when both people are relaxed, themselves, and open to where the evening leads.

💞 Modern Dating Etiquette, the Cheeky Way

We’ve hosted over 25,000 events across 65+ cities, and we’ve learned this: the most memorable matches come from people who focus on connection over convention.

Women often tell us they appreciate chivalry more when it’s genuine, not performative — when it comes from interest, not expectation.
It’s not about who pays the bill to impress; it’s about who shows up sincerely.

At MyCheekyDate, we believe modern dating works best when kindness comes first. Whether it’s offering to split the bill, picking up the first round, or planning the second date — what matters most is authenticity.

🌹 Our Cheeky Takeaway

So, who should pay on the first date?
Simple: whoever wants to.
Let it flow naturally, keep it thoughtful, and remember — the best gestures come from genuine chemistry, not social rules.

Because in the end, the most charming thing you can bring to a date isn’t your wallet — it’s your warmth, wit, and willingness to connect.

📝 Cheeky Thoughts: “It’s Not the Menu, It’s the Mindset: What 18 Years of Dating Events Have Taught Us”

In the Words of MyCheekyDate

Here we are — celebrating our 18th year of curating tens of thousands of dating events across 52 cities worldwide. After all those speed dates, Smart-Card matches, and countless cheeky conversations, we’ve learned something that may surprise you: sometimes the real dating challenge isn’t about who you’re meeting — it’s about the person looking back at you in the mirror.

💫 The Problem with the “Perfect Order” Mindset

We’ve seen it over and over again: daters put so many constraints on who they think they’re supposed to meet that they miss the people right in front of them. It’s like ordering from a restaurant menu — but dating isn’t a restaurant.

You can’t treat it like a job interview or a buffet where you tick off every checkbox: height, career, city, hobbies, dog ownership, and favorite wine. Chemistry doesn’t care about checklists. It just shows up — or it doesn’t.

When people approach modern dating like they’re curating a “perfect order,” they often end up missing out on something far better — the unexpected connection.

❤️ What 18 Years Have Taught Us About Real Connection

In fact, after 18 years, we’ve noticed a pattern:

The more someone demands, the less they often offer in return.

At MyCheekyDate, our best matches come from guests who are open, kind, and willing to be surprised. They’re the ones who approach each introduction with curiosity rather than criteria.

Our biggest piece of advice?
Get out of your own way. Be open to the unexpected. Step outside your comfort zone and let yourself meet someone who might just surprise you.

🌹 Where True Chemistry Begins

Because at the end of the day, the best connections aren’t about checking boxes — they’re about opening doors.

And sometimes, that door leads to a kind of chemistry you never saw coming — the kind that makes you forget about lists, rules, and algorithms altogether. That’s where the magic happens — and that’s exactly why we do what we do.

The Surge of In-Person Dating: Why Singles Are Ditching Apps for Real Connection

💫 A Quiet Revolution in Modern Dating

After nearly a decade dominated by swipes, DMs, and digital fatigue, something unexpected is happening — singles are craving real connection again.
Across cities like New York, Los Angeles, Chicago, and Sydney, attendance at in-person dating events has surged. Venues once reserved for post-work cocktails now hum with conversation, laughter, and the spark that no algorithm can replicate.

At MyCheekyDate, we’ve watched this transformation firsthand. Our events have seen record attendance in 2024 and 2025, especially among professionals and creatives who’ve simply had enough of curated profiles and ghosted messages.

📱 Why Dating Apps Lost Their Magic

Dating apps promised efficiency — yet created overwhelm. Studies show users spend an average of 90 minutes per day on apps, but report less satisfaction with matches.
Endless scrolling, mismatched expectations, and the rise of “textationships” (relationships that never leave the chat) have made dating feel transactional instead of emotional.

The pandemic years only amplified that. After so much screen time, many realized what they were truly missing: authentic chemistry, tone of voice, eye contact, and presence.

🥂 The Return of Real-World Connection

In-person events — especially those with structure, warmth, and personality — are filling that gap. At a MyCheekyDate evening, daters meet up to 15 people in one night, each conversation guided but never forced.
There are no pings, no profiles, no performance — just genuine energy between two humans sharing a moment.

Our hosts create what we call the “Cheeky-Chic atmosphere”: elegant venues, ambient music, and an easy social rhythm that feels miles away from the chaos of apps.

💌 The Data Behind the Movement

According to 2025 dating trend reports, in-person introductions are up 37 % year-over-year, while app usage among 25- to 40-year-olds has dropped by nearly 20 %.
Even the largest dating platforms are scrambling to host “live mixer nights” — confirming what we’ve always known: people still meet best when they’re face-to-face.

🌍 Where the Movement Is Happening

From Austin’s Oak Hill Social to London’s The Soho Residence, MyCheekyDate’s events are part of a global return to dating with intention. Singles want to laugh, flirt, and feel something — not just swipe through profiles on the sofa.

And the beauty of in-person dating? You can see attraction unfold in real time — the body language, the spark, the subtle smile that says, “Let’s see where this goes.”

❤️ Why It Matters

Dating, at its best, isn’t about technology — it’s about humanity.
That’s the heart of MyCheekyDate’s mission: to remind people that meeting someone lovely can still happen in a beautiful room, not just a digital feed.