How to Take Your Dating Game to the Next Level

Dylan Thuras: So Eden, I wanted to start by asking: What is the date that you have planned that you are the most proud of?

Eden Dawn: I’m in Portland, Oregon, and out on the west coast we have Tillamook. So out in Tillamook, which is a pretty little town, one first step as to many good dates, stop for Mexican food, because almost every date is made better with chips and guac and a margarita. Then you go to the Tillamook Bay and you go nighttime, moonlit kayaking. And so my husband and I upped it a level based on a tip we had heard—I don’t even remember where, because I wish I could credit them—of taking a bunch of glow sticks with us.

So you go out at sunset into the bay and you’re paddling around and it’s so calm you can have zero experience in a kayak. You do not have to do anything. But you’re getting into the water. We were paddling around. We were looking at, like, the beavers had put all these little homes together. There’s lily pads. The sunset goes down. It’s absolutely stunning.

Then the stars come out and you break all your little raver glow sticks and you put them around your wrists and your head and your boat. And so then you’re just paddling in total darkness where all you can see are your little glow sticks moving around underneath the stars. It was one of those days where I was like, if that was our last day on earth, that was, like, a good day.

Dylan: I think this reveals maybe Pacific Northwest versus Midwestern difference, but I fully thought you were going to be like, go to the Tillamook Creamery and, like, try all the cheeses. And I was like, yes, best day.

Eden: That’s just like a Tuesday.

Dylan: That’s the Midwesterner in me. I’m like, yes, cheese tour, best first date. I’m Dylan Thuras, and this is Atlas Obscura, a celebration of the world’s strange, incredible, and wondrous date spots. We’ve always wanted to make a dating episode for the show, largely because it comes up. I talk to people and they say, “Oh, you know, I went on my first date at an Atlas Obscura spot.” And usually it’s a nice story. I usually only hear these stories when they’re like, “now we’re together.” It’s not usually like, “and that was it.” I just think that going on dates to kind of strange and unusual places is sort of a good dating strategy.

So we’re here with Eden Dawn, the author of several books that specialize in travel and dating, books like The Portland Book of Dates and The Seattle Book of Dates. She has co-written these books with her partner, Ashod Simonian, and Eden’s here today to answer some of our dating questions. What kind of out-of-the-box date spots work? How to navigate traveling with a new partner? You may also hear some embarrassing stories from my dating past.

This is an edited transcript of the Atlas Obscura Podcast: a celebration of the world’s strange, incredible, and wondrous places. Find the show on Apple Podcasts, Spotify, and all major podcast apps.

Dylan: So Eden, you’ve lived in Oregon your whole life. I can kind of feel it, like in that description of that date, it is this magical, ethereal, beautiful set piece. I feel like that’s got a Pacific Northwest vibe to it. But you’re a journalist who’s written a ton about Portland. Your husband, Ashod, is also your co-author of your dating book, so you have a quality assurance tester involved here. What inspired these books?

Eden: When Ashod and I started dating, we really were trying to impress each other. So we did this thing called 23 Picnics where we were like, let’s each come up with 23 ideas—it took us like a year—of these incredibly special spots to go have a picnic. And so some might be hiking to the back of a waterfall. Some might be meeting friends out at, you know, in the city for whatever, a beer over sunset. But we had all of these ideas and people started kind of stealing our itineraries, being like, “Hey, that looks really fun. How—can you write …?” And then before I knew it, I was writing whole itineraries for weekends away for people.

Dylan: You were doing like, that’s competitive dating you were doing. There’s a kind of, you’re like …

Eden: Oh yeah, it’s ridiculous. With two Leos, we’re both like, “I gotta be the best! Look at me!”

Dylan: Do you remember your first date as a teenager? Was there like, was there a cool spot to go dating?

Eden: Oh, 100 percent.

Dylan: What was your first date?

Eden: So I grew up in Salem, Oregon. And in the ’90s, we had Skate Palace, 11 or 12 years old, roller skating at Skate Palace, holding hands with Randall Van Landingham and skating to Bryan Adams, literally probably the most romantic moment of my entire life.

Dylan: When I was in high school, I think I was a sophomore, and I wanted to date, I think she was a junior or senior, she was out of my league by a huge degree. But I was like, okay, I was like, all right, we’re gonna do a date in the high school. Come meet me in this conference room at midday, like lunchtime. This is brutally embarrassing, actually, now that I’m saying this story out loud. I brought a tablecloth and candles and music and I had made food, and I brought—and she was like, I think I think she was impressed. I also think she was like, okay, that’s a little much. I had aspirations at a young age.

Eden: Dylan, I applaud young you for putting in the effort. It’s the effort, that is the thing when it comes to dating that people want more than anything. It just inspires people to kind of be like, we need a plan. We need something to do because we can’t spend the rest of our lives sitting around for each other every day going, “What do you want to do for dinner?” which is so much of adult life.

Dylan: Let’s get into some specifics. We got some date travel questions from listeners. So I think we are going to hear one of those now.

Nick: Hi, my name is Nick. All right. I’m just bored of the endless bars, but I also don’t want to overcomplicate things, and like to be able to just chat with someone. Do you have any ideas for first dates that would kind of split the difference between the two?

Dylan: All right, what do you think, Eden?

Eden: Yeah, I think for first dates, and also being very money conscious, because how much do you want to—and especially if you’re somebody who goes on a lot of first dates. I know this is going to sound very basic, but I’m telling you it’s a good date, and it’s to ask somebody to meet you at a cute coffee shop, get your coffees to go and plan a walk nearby. Like it’s so simple. And also an increasing amount of young people are sober, so the bar is not necessarily the hangout that it was in my generation.

Dylan: Yes. I think that is really good advice. I have, this is a weird—okay, here’s a question I have. Like I said, my wife and I’ve been together forever, so this isn’t like a problem I’ve run into. But I have invited just friends or people I have met, I think I have freaked people out a few times, because I’m like, come meet me at this weird tunnel. You know, I brought some snacks and beers, let’s go climb into this tunnel and hang out. And I feel like a couple of times I’ve forgotten that some people are not at that comfort level. Maybe they feel like “I need to know this person better before I climb into a weird tunnel with them.” So maybe there’s like—what number date can you say, “Let’s go climb into this tunnel”?

Eden: Yeah. I do think I’m going to put out a PSA. Women, don’t be climbing into tunnels with men you don’t know on a first date. I’m just going to say, I feel like that’s, you know, good advice. Well, I think you have the simple kind of walk-and-talk dates. You literally meet for a donut and then go for a neighborhood cruise because you’re like, let’s go see all the flowers in bloom. Any of that’s adorable. And on that date, you’re like, what do you like to do? Are you an adventurous person? Would you be interested in going into a cave sometime? You know, you do have to, at the beginning, gauge people’s interests, because for sure, not everyone is going to want to do those things.

Dylan: Right. Gauge these, build up to these. Okay. I got it.

Eden: Yeah. I think you build up to some of that stuff. You make sure—and also, that stuff’s special to you. So you hold a little bit of the special stuff, because you want to share it with somebody who’s—nothing is more of a bummer than to share something you really care about for it to fall on a flat audience.

Dylan: Yes, totally. All right. So when we told people we were, you know, answering dating questions, we got a bunch of people about to embark on a true rite of passage in a new relationship, which is their first overnight vacation, their first overnight trip with a new significant other. So people called in to tell us about these and had some questions.

Eden: I love it.

Sam: Hey, this is Sam from St. Louis. I’m about to go on my first vacation with my girlfriend. But I’m very nervous about the eating part of it. I hate to admit it, but I’m a super picky eater. It’s easier to hide it when you’re at home, and I can choose restaurants or at least scout them out beforehand, but it’s a more of a gamble when we’re traveling. I’m terrified of seeming boring or lame. Do you have any tips for navigating being a picky eater while traveling? And also trying to impress somebody?

Dylan: Interesting. That’s kind of a tough one, actually, because, like, I feel like food is such a big part of traveling and, you know, it might feel like a little bit of a damper if your person you’re traveling with has got very narrow restrictions. What do you think? What’s your advice here?

Eden: Here is a trick that I have used many a time when on group vacations or whatever. Yes, it is a little bit of effort, but you plan things really carefully. However, you do the research, you look at the menus, you find all these places. There’s a ton of stuff. There’s Eater. There’s all the regional journalists. Look on Reddit. Like, I can’t tell you, there are all the places you can go. So find five, six restaurants that you feel okay with, and then you offer those to your girlfriend.

Dylan: Switching gears a little bit. So your book is really about exploring your hometown, your home state, your city. All right. We have a question from a listener who wants to know something about this.

Camila: Hi, my name is Camila. So my partner and I have always been tempted to stay overnight in a hotel, like in our own city, but it’s like for a special date night. But it feels like I don’t know, maybe it feels like a waste of money. Like, are we allowed to do this? I mean, we live in a big city, so it’s very expensive. So I will be staying in a hotel that’s 20 minutes away from my house. But then like, what’s the best way to make the most of it?

Dylan: I struggle with this, too, because this is a thing that my wife and I will do. Well, I try to. But it’s always like, “Are we really going to go and spend a bunch of money, like half an hour from our house? This feels dumb,” and usually ends up being really great. But like, I’m curious about what you think about it.

Eden: Yeah, here’s what I would say. If you’re going to do that, go to a hotel that has a bunch of amenities you want to use. And with a hotel, you can access those amenities before you check in, and usually after you check out to an extent. So like, does this place have a killer pool? Do they have a spa sauna? Do they have a hot tub? Do they have any of that stuff? Because, you know, now check-ins are like three or four.

But if you’re going to go do it, get up at 9am, go to that hotel, have an entire swimming day, sit by the pool or in the hot tub, drink your fruity cocktails, hang out, any of that stuff. And so that by the time dinner rolls around, you’re already loosey goosey, right? Like you’re having the best day ever. And I would really enjoy it.

So again, if you’re going to do it, have a place where you like the restaurant, because it doesn’t make sense to go pay all the money at a hotel and then not be there. So either eat there, or maybe it’s across the street from, you know, a venue where there’s a show going that you really want to go, and then it’s just adding on to that night. But I think it’s worth it if you can extend it and make it feel special. I wouldn’t do it just to do it. I would do it because you’re like, hey, I’ve always wanted to go to the spa here and you can only do it if you spend the night and so then it seems worth it. Otherwise, I think it’s worth it to look at going slightly outside your city.

You know, we are in Seattle, you have downtown Seattle, and then you have all of the islands, you can hop on a ferry and go an hour away. So you don’t have to get on a plane, you don’t have to drive far. But it’s worth it to spend 45 minutes to go someplace. And you can do that in a weekend without taking off a lick of work. And I think that that is slightly more than a staycation, but not much. You know what I mean? And that might feel a little more bang for your buck.

Dylan: Yeah. Okay, last question. And maybe with a specific place in mind: What is your dream date? Is there something you’re dying to do that you’ve never done? Or maybe you’ve done it and it was just true pinnacle experience? But what’s your dream date place?

Eden: You’re—this is a weird one.

Dylan: Go on.

Eden: I want to hold a baby elephant and I kind of want one to sit on me.

Dylan: I genuinely did not see that answer coming.

Eden: So I know there are a couple of elephant animal sanctuaries in Thailand. I have not done the full research to which ones, so I cannot tell you the exact name. But I follow a couple of them. And there are just these baby elephants. And now it’s also very sad because it means they’ve been orphaned by poachers and very bad people who I want to do very bad things to. But looking at, I don’t know why, I just, I love animals, and the idea of hugging a baby elephant that’s just like tackling me out of the way, I desperately want to do it.

Dylan: That was Eden Dawn. She’s a journalist and podcast host and the co-author of the books, The Portland Book of Dates and The Seattle Book of Dates along with her husband. They are at work on their Nashville version of the book and that will be out in October.

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This episode was produced by Manolo Morales. Our podcast is a co-production of Atlas Obscura and Stitcher Studios. The people who make our show include Doug Baldinger, Kameel Stanley, Johanna Mayer, Manolo Morales, Amanda McGowan, Alexa Lim, Casey Holford, and Luz Fleming. Our theme music is by Sam Tyndall.