Fancy a Bit of Matchmaking, the Cheeky Way?

💛 Fancy a Bit of Matchmaking, the Cheeky Way? 💛

We wanted to bring a fresh alternative to the endless forms, contracts, and hours of consultations that so many matchmaking services rely on.

While other matchmakers boast of thousands of daters (without saying where they come from), we actually meet ours — every week at our curated, host-led events. That gives us a fantastic pool of genuine, real-world singles to choose from — the kind of people you actually want to meet.

Sought after for the quality of our daters, the personal service we offer, and our distinctly cheeky charm, MyCheekyDate Matchmaking is effortless, elevated, and a little indulgent.

We’re honored to find that special someone just for you.

✨ Simplify Me!

A light, lovely introduction to matchmaking — perfectly suited for those ready to dip their toes into something new.

• Two pre-arranged Date-Nights, each with a different partner chosen for you based on your mutual aspirations, expectations, and likes.
• Matchmaking by our experienced team — a thoughtful, human approach to understanding you and finding your complement.
• A personal consultation upon confirmation to discuss your preferences and details.
• Date arrangements at one of our preferred venues (or a venue of your choice).
• Complimentary admission to our Speed Dating events for the duration of your package.

Originally $695.

✨ Date Me!

A step beyond the basics — for those ready for a bit more connection, attention, and flair.

• Four pre-arranged Date-Nights, each with a thoughtfully matched partner.
• A comprehensive matchmaking process led by our experienced team.
• A detailed consultation to understand your goals and preferences.
• Elegant arrangements for each Date-Night at one of our partner venues — or your own favorite spot.
• Enjoy our signature “This, That & The Other” concierge service — from fashion advice to unique date-spot recommendations. Ask, and you shall receive.
• Complimentary admission to Speed Dating events for the duration of your package.

Originally $895.

✨ Indulge Me!

Our most luxurious experience — for those who believe love deserves the red-carpet treatment.

• Six pre-arranged Date-Nights, each with a carefully selected partner chosen based on compatibility, lifestyle, and goals.
• A detailed and personal matchmaking process — comprehensive, intuitive, and truly bespoke.
• A one-on-one consultation to explore your preferences and desires.
• Custom arrangements for all Six Date-Nights at one of our preferred venues or a location of your choosing.
• Enjoy our “This, That & The Other” concierge service combined with a sampling of our Advice Package — from wardrobe guidance to meaningful insights designed to elevate your dating journey.
• Complimentary admission to Speed Dating events for the duration of your package.

Originally $1,195.

Because love shouldn’t feel like logistics — it should feel like laughter, connection, and a bit of cheeky fun.

Find your perfect package — and let’s make meeting someone lovely as effortless as it