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Can't go wrong with the Sapphire Hotel. I like it for dates because it's intimate without being intimidating. + they have great cocktails.
I was also going to say sapphire hotel!
Op, update us, how did the date go?
Also curious!
For future dates, Scotch Lodge is our (wife’s) jam. It’s damn solid across the board.
If you can get a reservation Janken is beautiful with delicious food. Went there yesterday (not my photo). It’s has a great atmosphere and the waiters are very attentive.
It sounds like they already know each other. I went to Janken with a friend, we each got fish, a side, edamame and dessert and it was under $80 a person. Agree that first time date should be lower key but OP sounded like they wanted to take them somewhere nice.
Perhaps the best date spot in Portland is the actual cave at Les Caves, Alberta’s subterranean wine bar. For the out of the box couple. She is going to live it there! Good luck
Had a great first date there, after amazing omakase at Zilla. Great drinks and the cave is perfect for inappropriate first date canoodling
Try the Box Social. This unassuming cocktail bar on North Williams is, in fact, an intimate spot for an inexpensive drink, whether it’s a rotating spritz or a flight of mini-cocktails. Hope you have a good time!
No one has asked yet: What age group are you in? 20s? 40s? And what is YOUR favorite sort of place/activity? What do you know about her interests?
We're both in our early 30's. I'm pretty much down for anything, but I like trying new eclectic or well hidden spots, or doing something fun like batting cages or something. She's pretty adventurous from what I know, and is usually up for trying new things.
I done Axe throwing as a fun activity date. Since it’s the Holidays, Peacock Lane or the Grotto are great for Christmas lights. While I haven’t been myself, I have had a lot of recommendations for EaT Oyster Bar if you like seafood/Southern food.
I would try a nice speak easy
Me and my partner have been wanting to go to Portland's Japanese Garden for a date. Spring and fall are the best season to visit the garden but winter visits are still majestic, nevertheless. And there is a japanese cafe so if your date loves asian cuisine then I really think uou should take her here. From a girl's point of view here's a tip, you can never go wrong with nature dates. Good luck!
Expatriate!