From Pearl District lounges to Alberta Arts cocktail spots and Nob Hill hideaways, Portland is built for conversation and connection. MyCheekyDate hosts host-led speed dating events across the city — warm, welcoming, and a little cheeky. Prefer something more curated? Curated Introduction Packages are available in Portland, while those seeking a more private, premium approach can explore Luxury Matchmaking, a founder-led experience built from these same real-world communities.

🪞 It's all about you right now. Matchmaking and dating coaching are having a real moment — see the data behind it — and for a limited time you can get 50% off Curated Introductions, 25% off Advice & Coaching, or 35% off Luxury Matchmaking with code SummertimeMe.

Portland Speed Dating, Hosted with Experience

MyCheekyDate hosts professionally organized speed dating events in Portland, bringing together local singles for structured, in-person conversations, no swiping, no guesswork. With over 900 events hosted in Portland and more than 26,000 across 50+ cities, each evening follows a proven, host-led format refined over nearly two decades, with events taking place regularly at venues such as The Civic Taproom and Bottle Shop.

Events are ticketed through Eventbrite, with clear expectations and transparent policies. Because these are live, in-person events, schedules may occasionally be adjusted to keep things well-balanced and enjoyable, a deliberate choice to protect the experience, and your ticket always remains valid for a future Portland event. If you prefer not to attend a rescheduled event, you may request a refund. It’s all part of the Cheeky Guarantee, a simple approach built around flexibility, clarity, and making sure guests are genuinely taken care of.

“Fun, well organized, and a great mix of people — I’d definitely go again.”
— Trustpilot review

Transparency & Trust  |  How Our Events Work  |  Independent Reviews & Media