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The Best Portland Dates

Posted on May 16, 2023   |   Updated on September 30, 2025

Rachel Monahan

Eden Dawn is an expert in fun, and the co-author of “The Portland Book of Dates.” She offered her expertise in planning spring activities on the City Cast Portland podcast recently. Her winning combination is “funtivity,” plus drinks (no need for alcohol), plus snacks.

Great First Dates

“A really simple one that I have recommended, especially to my serial first-daters, because I recognize the cost adds up: just go down to Southeast Waterfront and go wandering around together. Maybe you get a juice and then you go into [the warehouse] Cargo, which is such a fun wonderland. It's a fun thing when you're going through stuff together. But also if you feel anxious, you pop out for a minute, and then you come back and you're like, ‘Here, I found a flamingo for my front yard!’

“Then something I love to do is take people to Soro Soro afterwards for the affogatos, which are amazing. So you warm up before you just sit down and stare at each other across a table.”

Great Long-Time Couple Date

“If you have been together a long time and it's your 10-year anniversary, or your 20-year anniversary, there's hot air ballooning that you can do out in Newberg, which is an utterly amazing thing to splurge on.”

My Personal Favorite: Date as Sleeping Pill 

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