Skidmore Bluffs

A classic first date idea, though not especially common at night, is having a picnic in the park. The Skidmore Bluffs are the ideal place for a nighttime feast: you’ve got an edgy industrial view, a hidden suburban environment for drinking carefully concealed (or not very carefully concealed) wine or beer, as well as a particularly radiant view of the sunset. For the picnic, try going French: buy a baguette (or vegan bread), goat cheese (or vegan cheese), and a bottle of imported red or white wine. Wine will fuel either a sentimental or an honest conversation, and you might get a real look at your potential partner very early on. Show up around sunset, preferably during the non-summer season because of the many added distractions (e.g. clowns with hula hoops). 

2206 N Skidmore Terrace

Ground Kontrol

Who doesn’t want to sit back, play Mario kart and have a beer on a first date? Ground Kontrol is packed with 60 nostalgic video games, plenty of pinball machines, and even live DJs. There is something for everyone here: even if you don’t like video games, it’s still a catchy bar with a rare futuristic theme. This is a place recommended for adventurous daters who want an experience. Not that first dates aren’t always experiences. Also for those more frugal by nature: try Ground Kontrol on the 2nd Thursday or last Wednesday of the month when all games are free (5 pm to close). If you can correctly identify one of these two dates on the calendar, you should plan your date accordingly. 

511 NW Couch St. 

Rimsky-Korsakoffee House

Probably the most absurd setting for a first date imaginable: the haunted Rimsky-Korsakoffee House is prone to both live piano as well as an upstairs bathroom with faux feet dangling out of the walls. Though located with much subtlety off to the side of East Burnside in an aged craftsman, the Rimsky-Korsakoffe House is open from 7 pm to midnight. These hours are absolutely ideal in terms of contributing to the ominous vibes.

The Rimsky-Korsakoffee house hosts a sizeable selection of delicious desserts and coffee drinks. Note: there is NO alcohol here. But if you are interested in a late night caffeine rush, your date may actually last longer (even if there isn't a second date). 

707 SE 12th Ave.

Portland Aerial Tram

One of Portland’s most overlooked attractions, the Portland Aerial Tram might suffer from being a bit too romantic. Start by walking along the SW waterfront and for the price of a bus ticket (or literally just a bus ticket), you can ride the Portland Aerial Tram and get one of the most moving (literally) views of Portland. Also, make sure to bop around the fairly new, state of the art hospital before taking the aerial tram back down to the waterfront. The aerial tram is quick but it is effective: it is very likely that it’ll show you a side of Portland and maybe even your potential partner that you wouldn’t have otherwise witnessed. This one’s great for those with a childlike sense of wonder. 

3303 SW Bond Ave.

Portland Japanese Garden

Even if your date goes sour, the Portland Japanese Garden guarantees you at least three solid Instagram photos. The Portland Japanese Garden occupies 5.5 acres and is widely considered to be one of the most authentic of its kind in the continental US. Be careful: the Portland Japanese Garden will also occupy your heart, and possibly the heart of your date. There is a strolling pond garden, a tea garden, and a sand and stone garden all within these grounds. The Portland Japanese Garden breeds a sense of exoticism, serenity, and yes – romance. Plus, when you’re done, you’re still in Washington Park! 

611 SW Kingston Ave.

Helium Comedy Club

On most Tuesday nights, there is free standup involving some of the most noteworthy local comedians at the Helium Comedy Club off of SE Hawthorne. Drinks are especially cheap, comedians are expectedly ridiculous, and this is the perfect place to pick up inside jokes with any potential partner. In fact, comedians often crack jokes here about their own dating lives, many of which are rooted from the Internet. Suggestion: get dinner and talk first, then go to the show and get drinks. The Helium Comedy Club is a safe bet for a good date as laughter can produce endorphins, which could mean happiness. And truthfully, first dates are kind of funny; you might as well be more honest about it. 

1510 SE 9th Ave.

Lone Fir Cemetery

It might seem a tad peculiar to want to experience a first date in a cemetery. But if you want a first date that you and your date will both remember, this is a logical option. Southeast Portland's Lone Fir Cemetery is not just any cemetery: it’s an antique that houses one of Portland’s largest concentrations of botanic gardens. Bring a coffee or a picnic basket and stroll through the graves before nesting on a bench or in an unoccupied area (e.g. unoccupied by a deceased person). One thing you can definitely count on here: some peace and quiet. Unlike at a noisy bar or club, conversation should be easy and accessible. 

SE 26th Ave.

First Thursday

If you’re not so taken with the idea of a first date in a graveyard or a haunted house (even if it is October), you will probably enjoy the more traditional First Thursday. First Thursday combines wine, art, and music as part of a comprehensive grouping of art galleries all conveniently located near one another. First Thursday will familiarize you with local artists and the blend of art and alcohol could inspire abstract conversational topics that encourage deep conversation with your date. After all, you might as well get right into it.  

OMSI After Dark

Do you remember field trips? Everybody loved those. A late night date at OMSI After Dark (a.k.a. the Portland natural science museum) is like going on a trip down memory lane – with booze in hand. Each month, there is an OMSI After Dark night with a novel theme and an exclusively 21+ crowd. You get to be the kid at the science museum without actually having to be around any kids. Also, when the science becomes too much, you can wander out into OMSI’s backyard and take in the tender view of the river. First kisses may ensue. And with a spot this romantic, the first kiss is unlikely to be the last. 

1945 SE Water Ave.

Oregon Zoo

Sometimes the best dates are those that uncover some necessary nostalgia. The Oregon Zoo is a great bet for a first tinder date because you can be childish if you want to be (e.g. stuffing cotton candy into your mouth while mocking the less subtle movements of orangutans), distracted if you want to be; and also, romantic if you want to be. This first date will stand out because truthfully, how often does one go to the zoo without children or without being a child? Letting out your inner child can encourage a playful attitude that may eventually lead to more complex emotions. 

4001 SW Canyon Road