From the indie lounges of Uptown to the waterfront energy of Jack London Square, Oakland offers endless date-night character. MyCheekyDate hosts host-led speed dating events across the city — lively, social, and wonderfully cheeky. Prefer something more curated? Curated Introduction Packages are available in Oakland, while those seeking a more private, premium approach can explore Luxury Matchmaking, a founder-led experience built from these same real-world communities.
👻 Boo! October is the month singles stop ghosting and start dating. See why the numbers peak now. For a limited time, get 50% off Curated Introductions or 35% off Luxury Matchmaking with code CheekyBoo. When does it vanish? We're not telling.
NOVEMBER 7TH 2026 | SATURDAY NIGHT SPEED DATING @ IRON AND OAK RESTAURANT AND BAR | AGES 25-39
Saturday Night Speed Dating @ Iron & Oak Restaurant and Bar - November 7th 2026
Ages: 25-39 | 5PM
1001 Broadway, Oakland, CA 94607
Early Bird Admission - Ends 11/02 | $32.95
Regular Admission | $36
NOVEMBER 8TH 2026 | SPEED DATING @ IRON AND OAK RESTAURANT AND BAR | AGES 32-44
Speed Dating @ Iron & Oak Restaurant and Bar - November 8th 2026
Ages: 32-44 | 5PM
1001 Broadway, Oakland, CA 94607
Early Bird Admission - Ends 11/03 | $32.95
Regular Admission | $36
NOVEMBER 21ST 2026 | SATURDAY NIGHT SPEED DATING @ IRON AND OAK RESTAURANT AND BAR | AGES 25-39
Saturday Night Speed Dating @ Iron & Oak Restaurant and Bar - November 21st 2026
Ages: 25-39 | 5PM
1001 Broadway, Oakland, CA 94607
Early Bird Admission - Ends 11/16 | $32.95
Regular Admission | $36
NOVEMBER 22ND 2026 | SPEED DATING @ IRON AND OAK RESTAURANT AND BAR | AGES 32-44
Speed Dating @ Iron & Oak Restaurant and Bar - November 22nd 2026
Ages: 32-44 | 5PM
1001 Broadway, Oakland, CA 94607
Early Bird Admission - Ends 11/17 | $32.95
Regular Admission | $36
Oakland Speed Dating, Hosted with Experience
MyCheekyDate hosts professionally organized speed dating events in Oakland, bringing together local singles for structured, in-person conversations, no swiping, no guesswork. With over 800 events hosted in Oakland and more than 26,000 across 50+ cities, each evening follows a proven, host-led format refined over nearly two decades.
Events are held at Iron & Oak Restaurant and Bar in downtown Oakland, offering a warm, modern setting for relaxed, in-person connection. To keep things balanced, we monitor attendance and may occasionally adjust the schedule in advance, a deliberate choice to protect the experience. Your ticket always remains valid for a future Oakland event, and 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.
“Great experience — well organized and I met some really awesome people.”
— Trustpilot review
Transparency & Trust | How Our Events Work | Managed Room Quality | Independent Reviews & Media
The Cheeky Guarantee
If MyCheekyDate reschedules or cancels your event, you may request a full refund to your original payment method. Simply contact us directly and we’ll take care of your refund from there and make sure it gets processed. If your own plans change, your ticket remains valid as flexible credit and never expires, so you’re always welcome to reschedule for another event.