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.


AUGUST 26TH 2026 | SPEED DATING @ KIMPTON HOTEL VILLAGE PORTLAND | AGES 25-39

Speed Dating @ Kimpton Hotel Vintage Portland - August 26th 2026

Ages: 25-39 | 6:30PM

422 Southwest Broadway, Portland, OR 97205

Early Bird Admission - Ends 08/21 | $32.95

Regular Admission | $36.00 


AUGUST 30TH 2026 | SPEED DATING @ KIMPTON HOTEL VILLAGE PORTLAND | AGES 29-42

Speed Dating @ Kimpton Hotel Vintage Portland - August 30th 2026

Ages: 29-42 | 5PM

422 Southwest Broadway, Portland, OR 97205

Early Bird Admission - Ends 08/25 | $32.95

Regular Admission | $36.00 


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

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