How Portlanders are navigating the ups and downs of modern dating

“Think Out Loud” wanted to hear how people are navigating the dating scene right now. So we gathered a panel of “experts” to help us break it down.

Sarah Ruby Armstrong is the creator of Dating Profile Tune-Ups, Playdates and Kissing Booth Social Club. Taylor Kravitz is a licensed marriage and family therapist, the CEO of Empowered Fulfillment Therapy, and an adjunct professor at Lewis & Clark College. Margaret Bagan is a marketing specialist in Portland and served as our resident dating single.

They bravely joined us in front of a live audience at Portland’s Revolution Hall to talk about the highs and lows of modern dating.

Note: The following transcript was transcribed digitally and validated for accuracy, readability and formatting by an OPB volunteer

Dave Miller: This is Think Out Loud on OPB. I’m Dave Miller. We have a special show for you today. We recorded it at an audience event a few weeks ago at Portland’s Revolution Hall. We called it “Dating Decoded.” It was an hour all about the lows and the highs of modern dating. Anybody was welcome in the audience, but we did advertise the event as a way not just to talk about dating, but to meet people, and there was time for mingling and games both before and after the conversation. There were three people on the stage with me. Sarah Ruby Armstrong is a creator of Dating Profile Tune-Ups, Playdates, and Kissing Booth Social Club. Taylor Kravitz is a licensed marriage and family therapist and the CEO and clinical director of Empowered Fulfillment Therapy, and Margaret Bagan is a marketing specialist in Portland. She served as our resident dating single. I started by asking Margaret what she’s looking for.

Margaret Bagan: I can tell you I’m not looking for just a date on a Friday night. I’m looking for a long term relationship, and I have been for quite a while. So that’s where it kind of gets tricky, because it’s easy to just go meet someone, but when I’m looking at online dating, which is what I’m doing now, I’m looking at somebody long term and so I’m really more critical than I would have been probably in my twenties. Because I’m 60 and it’s a weird time to be dating, for sure.

Miller: What do you mean by that?

Bagan: I just think I’m set in my ways, as are men set in their ways, and so you don’t want to go through what you don’t want to go through, and you just want to live out the rest of your life happy. So I’m just more critical in my dating.

Miller: You’re looking for a man.

Bagan: I’m looking for a man.

Miller: What else? I mean, what kind of person? So I mean, a long term relationship, not just a date on Friday night. What qualities are you looking for?

Bagan: I’m looking for somebody who’s independent on his own, because I spend a lot of time with my friends. I’d like to incorporate them into my friendships as well. But I also like my space, so I hear a lot about people that are married or dating, but everybody goes back to their own spaces. That sounds really good to me. I want someone in Portland too, and I’ve met a lot of great guys that don’t live in Portland. I seem to meet more guys that don’t live in Portland than guys that live in Portland that I match with, that I have attraction with and have chemistry with. So that’s kind of been my challenge.

Miller: And you said that mainly at this point it’s online, it’s using apps.

Bagan: Yep.

Miller: What’s your experience with apps in recent years? What’s it been like?

Bagan: It’s been good. I mean, it’s been good and not good. I have done Match and Bumble and I just got back onto Bumble three months ago, so I’m fresh back into the dating world and I’ve met a couple guys in Portland, but it didn’t go past one date. I just didn’t have any chemistry or they just weren’t my type.

Miller: How quickly do you realize that?

Bagan: Immediately.

Miller: Literally immediately. Does that ring true for other folks? Everybody. Who could share something about the Spidey sense of how you know, because it seems like an immediate thing. So how you know and how quickly you know that this is not gonna work?

Patrick Patterson: OK, so my name’s Patrick Patterson. The way I know is, I think the level of comfort that I feel with that person, how easily we exchange rhetoric, how easy it is to talk back and forth. And if I don’t feel defensive, if I just feel comfortable talking and sharing information, then it’s likely going to work.

Miller: And the sense you get is that that level of comfort, it’s not about newness. It’s not about awkwardness if you don’t know this person. It’s more deep and chemical and unchangeable.

Patterson: Yes, feeling like you understand me and we can relate. We have similar experiences.

Miller: And so you’ve been on dates where you didn’t feel that, but it’s minute two and you have to keep going.

Patterson: Yes. Although it’s been a few years since I’ve been on dates, but generally, yes.

Miller: Who else has felt that, that immediate sense of no, no, this is not gonna work? Because I’m curious how - I can’t see in the back, but I’m told there’s somebody there. What’s your name?

Amy: Hi, I’m Amy, and I think that you just know and you don’t have to figure out why you know whether you like them or not. I think that women don’t pay enough attention to their instincts and you should just know right away and if you don’t like them, you don’t like them, and that’s it. I mean, right?

Miller: Yeah.

Amy: I mean, I just, I feel like you can later be like, yeah, maybe he didn’t smell good or maybe his shirt was funny or whatever, but I just feel like there’s either a vibe or there isn’t, and you should just follow that.

Miller: We asked folks in preparation for this show that we had a survey and we got a lot of interesting responses to that, and one of the themes that came up in a lot of comments specifically about online dating is that – this is not a surprise – that plenty of people are not exactly honest in their profiles, about their age or their profession or their appearance or any number of things about who they are. Is that something that folks in the audience have experienced? Is anybody willing to admit that you were less than honest in your own profile?

You don’t even need to give your name if you don’t want to.

Speaker 1: So I will say that being online is very public, and I think our safety and our privacy is our own to manage. And I feel like there is no reason we have to be completely honest until we meet somebody in person, and we know them pretty well. So I think you can slowly unfold who you are and your personal details because going on dates, people dive deep right away and they learn a lot about you. I think it’s OK to withhold some information initially until maybe the second or third date. Or if you really, really vibe with somebody, sure, let them know every little tiny secret you may have not shared online.

Miller: Sarah Ruby, I should have said earlier that one of your many sort of relationship and dating related… This isn’t even a job, it didn’t start as a job. It started as, what, just like a kind of a past time.

Sarah Ruby Armstrong: It depends on how you define job.

Miller: But it was to, for free, give people advice for how to improve their dating profile.

Armstrong: Offering friendly objective feedback on your dating profile, no charge. Can you believe it? That was the sign.

Miller: So what did you learn by doing that? What didn’t you learn? Is that what that means?

Armstrong: So I mean, I spent four years talking to thousands and thousands of people about their dating experiences, and it was really just an entry point, right? It turns into talking about the problem of self-perception and how we talk about ourselves and how do we even articulate what it is that we want? So what didn’t I learn? I mean, truly, I don’t know where to even puncture that question.

Miller: OK, so you said one of the problems that is not necessarily only about men, and not all men, but more common among men is a lack of self-awareness, and we can come back to that question later this hour. What are some of the other pitfalls that you saw, common things that would come up over and over in the way someone would present themselves to the world?

Armstrong: I think a common pitfall in app-based dating besides photos, like we won’t talk about photo problems. That’s a different category. But I think it’s really easy to try and boil ourselves down [to] a distillate list of interests separated by commas: hiking, brunch, Netflix, reading. Like when you’re out in public and you see somebody and you’re like, that’s kind of, they’re kind of cute. I’m vibing with them. You’re not vibing with a list of their interests pinned to their arm, right? Don’t just say, here’s all of my interests, please pick one to connect with me on.

It’s more about how you talk about your interests, right? Don’t give me a list of 10 interests, pick one thing and just say something about it. It’s not about the thing you’re saying, it’s about how you say it, because I’m not seeing you in person. I’m not knowing what you talk like, our goal in app-based dating is to show people what it’s gonna be like to spend time with you and have a conversation with you, not if your list lines up, right? So talking about, just take a sentence and say something specific, no one cares if all the things line up. It’s more about, are you gonna be boring or unbearable to spend time with?

Miller: Taylor, how much do frustrations with online dating come up among your clients?

Taylor Kravitz: All the time. I work with a mixture of folks around dating, so there’s single folks who feel like they’re perpetually single and are longing to find a connection and feeling pretty exhausted by the process. There’s newly single folks who feel kind of excited and energized by dating. It feels really fun. And then I work with folks in relationships who are dating in a non-monogamous context or they’re dating to, I’m a sex therapist, so I work with folks around kink and BDSM who are trying to find partners to explore that kind of connection with. But across the board there are certainly lots of challenges that come up.

Miller: What are the most common ones?

Kravitz: I hear a lot of folks feeling a lot of pressure. I think because so much dating happens on apps right now, there’s like this tiny moment that you have an opportunity to present yourself to folks and I think for some that’s a little easier, but for others it can feel like a lot of pressure to try to sell yourself. And when we think about folks who experience marginalization in this world we live in, I think that can be even harder if you’re approaching dating as, let’s say a trans person or a person in a bigger body or a neurodivergent person or someone who’s disabled, it can feel like the system is not set up for you to be chosen, and that can feel really hard and discouraging. So I definitely see that a lot, a lot of feeling like pressure to perform.

Miller: Are there also, for some of those same communities you’re talking about, some benefits to the not in real life aspect of apps?

Kravitz: Yeah, I think for some there can be the safety of having this separation. For example, if a trans person is dating, it can feel very scary or risky to meet someone you don’t know who either knows about you being trans or you feel like you want to disclose that to them. That can be really dangerous, so it can feel like there’s safety in that separation. I also work with a lot of neurodivergent folks and I’ve heard from autistic clients that they’re like, I will not be caught dead in a bar or at a speed dating event, that’s my nightmare. And so they’re like, I like apps because it means I can be home in my cozy, supportive environment and get to pursue connections there, and then slowly build the comfort and meeting folks in person.

Miller: Sarah Ruby, you said that pictures on online dating apps are its whole specific world. We got one comment about that. When we asked folks about their experiences, one person wrote, “Ghosting, dick pics, male toxicity, and abusive language when kindly rejected. And why do so many men think it’s OK to post selfies from public bathrooms?”

Armstrong: So I actually only heard one question in that, which was about public bathrooms.

Miller: And that’s my question for you. So is this really a thing?

Armstrong: Yeah, sure, sure.

Bagan: They’re personal bathrooms as well.

Armstrong: OK, did you say, someone say please fix that? OK, well, I would like to let you know that I’m doing my part. And I think, on a larger scale, what a lot of people miss or underconsider when they’re putting together their dating profile pictures is all of the things that you’re saying between the lines of your photo, right? Like, it’s not your body and your face, it’s how filthy your bathroom is. Or how clearly it is that you haven’t cleaned your bathroom mirror in a very long time, right? That’s the thing that you’re at, like I don’t wanna come over if I can see the state that you keep your house in. We have to think about these things, like think about your shot. And people are always like, I don’t have enough, I don’t have any good pictures of me. I’m not good at selfies.

Dating is arguably one of the most important things you’re ever gonna do, right? Take the time and energy to get a picture or two that matters. You care about your LinkedIn profile picture, right? You care about what you put on your Instagram. Even if it’s just for hookups or you’re looking for the love of your life that you’re gonna spend forever with, we should be embarrassed that we’re not taking the quality of our dating profile pictures more seriously.

Miller: Let’s bring the mic over here.

Speaker 2: So on the other end, since this is an educational thing for both sides…

Armstrong: So glad you’re here!

Speaker 2: …one thing, I, when I swipe or when I’m on dating apps, it’s the first thing that I see in a lot of profiles, is no dead fish pics. Right, that’s a big one, and we haven’t touched that.

Armstrong: We haven’t touched that.

Speaker 2: We haven’t touched on that.

Miller: I may not be the only person who has no idea what that means. I know what a dead fish is.

Speaker 2: Yeah, yeah, so a lot of guys hold their fish like trophies in the dating profile, right, and they’re flexing and they got their fish, but apparently it’s unattractive to women. I see it a lot.

Miller: Did you bring this up because you have an equivalent that you’d like women to not –

Speaker 2: I have dead fish pics, but I don’t put them up thanks to the feedback on the dating profile.

Miller: Oh, you’re a fisherman who’s proud of your catch?

Speaker 2: Yes, absolutely.

Miller: Would you like everybody in the audience –

Speaker 2: And by the way, I don’t get a lot of pictures, but the pictures I do get are, hey, I’m out in the ocean. I’ve got this monster. I’m pumped!

Miller: I think it, I speak on behalf of maybe just myself to say, I’m proud of you.

Speaker 2: Thank you.

Armstrong: You caught that fish!

Speaker 3: OK, so I have two questions.

Miller: Let’s just do one question because there’s other folks. So choose the best one.

Speaker 3: OK, so we’re talking about pictures that we don’t want to see on male profiles. Can you give some feedback on what you want to see for male profiles?

Miller: I actually, I want to hear Margaret’s response to this first.

Bagan: I know I’m thinking really quickly like what do I, because I totally get the dead fish, but I also…

Miller: You mean like you don’t want to see him holding his fish up?

Bagan: Hey, if a guy loves to fish, show it. But I love just seeing a guy with his buddies, what he’s doing.

Miller: And the fact that he has buddies.

Bagan: And the fact that he has buddies because I’ve dated guys who have no friends, and that’s not a good sign. So I like seeing them at a football game or out enjoying fun with their friends, and then I can see what their friends look like. And if the friends are cute and good looking, then maybe he’s a great guy. Like I do. I’m shallow that way. I really am.

Miller: I wanna move from online dating or meeting people primarily online to meeting them in real life. Margaret, you said you recently turned 60. When you started dating, this was before apps, I’m guessing.

Bagan: Oh yeah.

Miller: What do you remember about meeting people when in your twenties, say?

Bagan: Well, you got a face with a voice at the same time. So that’s kind of the funny thing. There’s a show out called “Love Is Blind,” so people meet each other through a wall, but they hear each other’s voice and they can’t put it together afterwards. I’m having a hard time where I’m meeting them through the app and then I hear their voice and I hear how they speak and it’s a different thing.

Miller: You had an idea of what their voice is going to be.

Bagan: I’ve got a vision of what they’re going to sound like and they don’t. But back in my twenties, like you’d meet people out, you’d meet them through friends, you’d meet them at a party or at a bar, and so you got it instantly.

Miller: Taylor, we’ve had a lot of conversations on Think Out Loud in recent years about how schools and students are still experiencing sort of the lingering social effects of the pandemic. Do you think that’s still affecting dating?

Kravitz: Yeah, I think I’ve had that come up with some clients where, I think we got so used to connecting with folks online and that way of viewing relationships that it can feel quite uncomfortable for some to connect in person, kind of feels like we still kind of keep to our own little bubble, our own familiar people, and that branching out to connect with others is less likely to happen. I definitely hear that from young folks a lot, who developed socially during the pandemic. I mean that was like, it’s like when you learn how to be a social being in a lot of ways, it’s in these developmental years and for so many it’s like COVID took that time. Yeah.

Miller: So how do you help people? If they want to be more social, more comfortable around other people in the moment, where do you start?

Kravitz: Well, one thing I talked to folks about is what do you value? What do you enjoy, like starting with just building community around those things that matter to you. So I think you’re more likely to meet folks with shared values, interests, ideas, beliefs, if you’re engaging in those communities. That might be like volunteering or going to a local meetup around an interest of yours. I think that’s a starting point. And then for some of my clients we’ll work on, if they have some social anxiety, let’s get to know the anxiety. Why is it there? What is it trying to protect you from? What are you afraid of and how can you be a little gentler with yourself? And maybe we’re practicing how do you wanna start a conversation with someone? How do you express yourself? What do you want people to know about you? So those are some starting points.

Miller: Sarah Ruby, one of the benefits of online dating is that you may not know exactly who the person you’re chatting with is, and they may want something different from a relationship than you do, but they’re there and you’re there because you both want some kind of short term or long term relationship. That’s not true with people you just see in a dog park or it may be true, but you’d have no idea, which is a huge difference, and then you have to somehow chat them up. You have to start it.

Armstrong: How have people been doing it this whole time?

Miller: How do we even exist?

Armstrong: Incredible. I don’t even know what we did before about 15 years ago.

Miller: I’ve seen a lot of, in the last 15 years or so, there have been a lot of articles about so-called the lost art of flirting.

Armstrong: 100%. Well and to –

Miller: So…

Armstrong: Go ahead.

Miller: I want to, let’s get a mic to you if you’re gonna – so what were you saying?

Speaker 4: I have some strong feelings around this question that you brought forth, and part of it is being comfortable with the uncomfortable. It isn’t always going to feel comfortable. And if you feel like this person might be worth your time, there is no harm in asking a question or introducing yourself and I don’t know why there’s such a fear. You have to be comfortable with that.

Miller: Do you not know why there’s a fear – to me it makes perfect sense because you’re putting yourself out there. You could be rejected.

Speaker 4: It is hard.

Miller: I mean, I’m not saying that they’re good reasons, but they make perfect sense why someone would be scared about putting themselves out there.

Speaker 4: 100%. But I feel like then, the reward from doing it though, whether you’re rejected or not is twofold too. You build confidence one way or another, right? And if you don’t do it ever, you just, in my opinion, retreat a little bit more, a little bit more, and then you need help to get you out of your shell.

Miller: Are you good at chatting people up in a supermarket line, say? Like if you see somebody who catches your eye, what do you do?

Speaker 4: Well, I think it’s more of I’m just Curious George. I’m just more like, hey, why did you pick that? Or that magazine looks interesting. And I feel like it’s just more, I’m more of a people person, but I wasn’t always that way. And the more you do it, the more reward you get for doing it too.

Miller: Can you go from sort of, gentle Curious George questions to, can I get your number?

Speaker 4: Yeah, it’s all a matter of respect and being respectful of someone. And if you can tell they’re super anxious about it or whatever, and it was just like, hey, I thought your shoes were fabulous. I wanted to say hi. I’d love to talk to you more, right? I feel like it can be a soft, gentle hello. It doesn’t have to be like, can I get your number?

Armstrong: To your point about the dog park though, I mean, it wasn’t your point about the dog park, but I do want to take this opportunity to speak to, I think dog parks are like the most under-celebrated adult social spaces for both connecting as friends and flirts because it doesn’t cost you any money. You’re on a regular routine, like you see people regularly, [it] takes a lot of the social anxiety out of things when you have the buffer of dogs, you’re just talking about the dogs. You don’t even have to look each other in the eye.

And to that same point it’s really easy for people to get hyper-focused on dating and why isn’t it working and why aren’t I connecting and this feels bad, and completely neglecting the practice of building other community and how important it is to make friends and find other interests because it’s often not the date that you go on that turns into the thing. It’s the friend that you made at that one thing that invited you to a dinner party and then at that dinner party, you met this other person… like you have to flex the muscle of socialization. It’s the same muscle as flirting and if you’re not doing it in other places, it’s not gonna work flirtatiously.

Miller: What’s your name and what do you want to tell us?

Emily: I’m Emily and I’m in agreement with the previous comments. I grew up in the Midwest being gay, and you have to get used to asking people, feeling out if they are gay. With same-sex relationships, especially in public, you really have to bet on yourself that you can navigate this world of trying to see if there is interest or getting your number or initiating, because usually in heterosexual relationships, this is always assumed to be the man’s job. And I think in in-person interactions, a lot of online dating is very external-based. You look at a picture, you’re getting a lot of external validation, but if you are approaching people in public, you may give people a chance that at first glance they may not be super attractive to you or you may not swipe on them, but you feel their energy, you feel their vibes, you see how people are connecting with them. So I think it really makes sense to really try to have the gumption to approach people in public.

Miller: We asked folks ahead of the show for the challenges that they’ve been experiencing with dating right now and one person wrote, “Monogamy, LOL. There are too many ethical non-monogamy folks, solo polys and couples looking for their unicorn.” A lot of yeses. So is that the general murmuring “yes” there, people who are looking for monogamous relationships saying it’s hard for you to find people who are also looking for monogamous relationships?

Armstrong: Ahhhh… sorry I didn’t meant to dissent so vocally.

Miller: OK, well, while we find folks who want to talk about that, Sarah Ruby can explain her “ahhh” sound, but please put your hand up so we can hear, we can get more of your personal experience as we hear Sarah Ruby.

Armstrong: No, I just think we’re all… I don’t wanna invalidate the experience of the straights and the monogamous. It’s a struggle, and I understand. But I think we all have, like as a non-monogamous person and when I hear other non-monogamous people talk, I feel like we all are saying the same thing. It’s like, oh, there’s no monogamous people in Portland. Like, ah, there’s no non-monogamous people in Portland.

Miller: So you, I mean this is a simple case in your mind of the grass being greener on the other side?

Armstrong: Yeah, like it is a challenge and a real labor to make connections and it’s easy to gripe about it when it’s not super easy and going. And I think the double-edged sword of our app-based way of existing in the world now, especially with dating, is this problem of unlimited options right before you. And so I should be able to find exactly what I’m looking for, but it still means you have to sift through all of the things that aren’t the thing you’re looking for.

Miller: All right, let’s go into the back of the room and then we have someone in front after.

Speaker 5: Preach. Sarah, you said it right there like I, as a man, am a bad communicator and that has been very present in my life recently. But what’s been more obnoxious is the way that, as a third party or a guest star or the poly – yes, you hear me – it’s obnoxious when I ask for a cuddle and it’s not received. I come from the Midwest also, but living on the West Coast is interesting to me where it’s free love and it’s this we can just live together, but then there’s more cliques and more red tape around, I can’t say that word, but the cuddling and the extracurriculars that go along with being “poly”, which is dependent on every person in that sort of relationship. Yeah.

Miller: Wait, I don’t feel like I fully understood what you’re… No, I’m serious, what…

Speaker 5: What reciprocity, yes.

Miller: So what do you, what do you feel like? What’s it hard for you to get that you want right now?

Speaker 5: Well, to everybody’s point here is the communication and just being clear about what is understood, what the boundaries are, and what relationships actually mean instead of being available when other people want you available and not being included in things that are lovey.

Miller: OK, and do I understand correctly that at base this is a response to that comment I read earlier from someone seeking monogamy saying, it’s easy for folks who are looking for some version of non-monogamy. You’re saying no, it’s not.

Speaker 5: Correct.

Miller: OK, we have another comment here in the front. What’s your name?

Mariah: Yeah, hi, my name’s Mariah. I am monogamous. I came to that after a lot of interrogation. And I’m also a person who is queer and likes to date people who are very much not on the relationship escalator and very much have done a lot of work around, OK, how do I create a relationship I want within a monogamous framework that I think is how I’m hardwired. My struggle in this with dating is, well, how do I advertise this? How do I say, well, I’m monogamous. Is this is a checkbox, is this is a category people filter on? And I’m not ending up with dates with people who are like, well, when do you want kids? When do you want to get married? Because that is super not how I’m thinking about this. It’s something I’m really

grappling with, on how to advertise that and how to find the right people sort of within that framework.

Miller: Right, because what you’ve just outlined is you figured out after, as you said, a lot of work, really what you want, and you were able to actually communicate that in 25 seconds, so it wasn’t like it was, I mean, and it was clear, it made sense, but you’re saying that it’s specific enough that it’s been hard for you to match with what you want.

Mariah: Yeah, I run in a lot of non-monogamous circles, so my friends have done their diligence in trying to find me some people who are well aligned, but ultimately I do feel like I often have to go to the apps just because it’s not really aligned with my social circles a lot of the time. And in those apps, what I’m often finding is I feel like I’m vibing with someone online. We reach the first date, and all of a sudden it becomes clear that they have a timeline. They have that. I don’t think we’ve talked about the relationship escalator yet, but it’s something I’ve really run into as a big issue of misalignment within dating in Portland, especially monogamously.

Armstrong: Can I ask you a question about your profile real quick?

Mariah: Please.

Armstrong: Does your dating profile have that language of the relationship escalator on it?

Mariah: It doesn’t. Maybe it should.

Armstrong: I think that kind of language is exactly, like it sounds like you, it sounds like a human being talking, it doesn’t sound like a list of things. Putting that first filter out of like, yeah, especially how you talked about I’ve worked through non-monogamy. Like I am at monogamy, very intentionally. I vibe well with people that do the similar kind of relationship craft and interrogation that polyamorous people do, but I am monogamous and want to be in a relationship monogamously with somebody who is not into the relationship escalator. Like, put that in there, girl, you’re gonna, it’s like a completely different category of dates you’re going to be getting. I’m so glad we were here to work this out with you. It’s wonderful.

Mariah: Thank you for the free advice.

Armstrong: It’s my specialty.

Miller: Taylor, one of the things that that has been coming up there though is just the how the menu of available options is more, there’s more possible communication about it than ever before and more awareness among some people about what they want and what they don’t want, but also more possibility for people to be on different pages about what they want. How do you navigate that as someone who’s helping people think about maybe the beginning of a relationship, or the middle of one or the end of one?

Kravitz: Something I explore with clients a lot is what their relationship values are. Our society gives us a lot of scripts for relationships, like the relationship escalator, but in addition, our society tells us this is what love should look like, this is what commitment should look like, this is how you should navigate freedom and sexual connection and like communication, we just get a lot of these scripts. So I think it’s helpful to examine, what are my values? What do these things mean to me, because if we do that we can give more clarity to potential partners.

I do want to highlight though, as a relationship therapist, I’ve seen folks work so beautifully together who are quite different and who might have different ideas and approaches on relationships, but they have this care for each other, curiosity, compassion, and they can find a way to build a relationship that works well.

Miller: Even if they actually want different things out of the relationship? It’s one thing to have a different outlook on life or to have a different approach, but you’ve seen it work even if they want literally very different things about the relationship itself?

Kravitz: Sometimes, yeah, I mean, I’ve definitely seen plenty of couples separate and not feel like the most supportive thing, but it’s so interesting because I think it depends on what we value the most. I’ve had clients who are like, yeah, this sexual relationship with my partner is not very satisfying. But I value these other elements of our relationship so much, even though that really matters to me, this other stuff matters more and so I choose them anyway. So I think that can be the case. I think we have to be intentional about what matters the most because we’re never going to find someone we’re aligned in every single way at all times for all of the life or relationship span together. We change so much throughout our lives, so it’s just impossible and so I’m like this optimist for working together, I guess. I think I’ve seen it.

Miller: What’s your name?

Margot: Hi, my name is Margot, and I was wondering if any of the panelists have any advice for a late Gen X widow in the dating scene.

Kravitz: I have thoughts, thank you for asking. First I wanna name, as someone who’s in big grief right now, that I see you and I care about your experience. And it takes a lot of courage to get that out there and date when you thought you had this relationship that you just wouldn’t have to do that again. My favorite thing when I feel uncomfortable is to, I call it meta-process, so I’ll just say the thing that I’m uncomfortable about to the person and see how they respond and if they respond well, I know we’ll vibe, and if they don’t, they don’t.

So for example, I was at my kid’s 5th birthday party and a mom came up to me and was talking to me and I was like, I’m having a hard time because my sister died and I feel weird because there’s grief and I also want to make friends with you. And she was super kind and she shared about her grief and I was like, OK, you’re someone I can talk to grief about and you can hold that part of my experience and we can also build a connection.

And so I think our society doesn’t set up folks well to know how to hold grief and it’s a deeply human experience that we all will navigate. And so I think if it felt right for you and you felt like you had that courage to say the thing of like, I know it might feel hard to date a widow, and it feels hard for me to hold grief and want to connect, what do you think of that? I think the right kind of person would probably respond well to that and not the right kind of person may totally fumble and make you feel uncomfortable and then you kind of know they’re not for you. That’s what comes to my mind, yeah, I hope it helps.

Miller: Margaret, one of the themes that’s been coming up is how folks communicate. I mean, often it’s online, but it doesn’t have to be, their expectations or their hopes or their desires for the relationship. How do you think about telling the world what you want?

Bagan: Online or in speaking to somebody?

Miller: Both, I suppose.

Bagan: Well, I don’t feel like I’m telling the world online. I feel like I’m telling a little community, even though it does go further than that, but more talk about my interests, not about what I want in life, but I talk about what I’m interested in, what my activities are. And I don’t say in my profile, and maybe I should, now that I’ve listened to this, I should say I’m looking, I mean, I do say a long term relationship. I do say I’m looking for someone with integrity and that’s kind and that kind of thing. But I think a lot of people think of themselves as being kind with integrity, so I mean I could go on and on about a really bad date I had in Lake Oswego a month ago, but I won’t.

Miller: Could you give us just a small taste of it?

Bagan: I think people look at themselves that way, and I’ll just say the guy showed up. We met at the Tap House in Lake Oswego, and he sat down and he did not stop complaining for five minutes. And so I think he thought he was a great guy, but he sat down.

Armstrong: You didn’t happen to give him that feedback, did you, post-date?

Bagan: No, I didn’t.

Armstrong: Oh, you should have told him. Maybe no one’s ever told him he complained.

Miller: Wait, so what is your recommendation for what she should have said?

Armstrong: Girl. I mean, that’s impossible. It’s very easy for me to sit here, not being in that situation and be like, you should tell this guy this thing. But I do think that especially in our modern era of dating where we are often so far removed from the people that we have gone on one unspectacular date with. Truly, what a gift it is to offer feedback. Like it’s gonna be uncomfy for sure, for sure. But like, what if no one’s ever told him that like…

Miller: That he’s obnoxious.

Armstrong: That he’s like a complainer.

Miller: Well, no, I mean that’s what we’re talking about, like putting it in one word.

Armstrong: Well yeah absolutely, like, hey, honestly I just kind of knew right away because the first five minutes you didn’t stop complaining. That’s such a short amount of, it’s such a short text of information. And you don’t owe this guy anything. You’re not going to see him, like…

Bagan: That was my thing. I’m never going to see him again, so I wasn’t worried about it.

Armstrong: Yeah, like what do we owe? Is it our responsibility?

Audience Member: But should she tell the truth when he could become violent towards her?

Armstrong: That’s totally fair.

Miller: The question from the audience was, does she owe him the truth when he could become violent towards her?

Armstrong: That’s totally fair. Yes, and. Although I do think that, well, one, I mean, you’re probably not, does this guy know where you live?

Bagan: No.

Armstrong: OK, but I do, as a side note, I do think that that sidebars the problem of women behaving differently because men are unsafe rather than expecting men to behave better, like a core level. But no, like we don’t owe people anything, right? But I do think that we’re in this new era. We’re having so many varied kinds of connections now and to say maybe we do not owe each other or owe anybody, but if we’re out here doing it anyway and we’ve already spent this time, if it’s really easy to just tell somebody like, hey, you’re a real bummer. The first five minutes of that sucked. Like, who knows? It could be transformative. He might invite you to his wedding.

Bagan: Oh God, no.

Miller: I’m gonna flip it a little bit. We’ve been talking for a little while now about if and how to tell somebody what you feel about what they did. I’m curious what you all have learned about yourselves from dating. Does anyone have any thoughts they want to share? Raise your hands if you want to. I mean, I ask it because we’ve been talking about vulnerability, about putting yourself out there, about figuring out what you want and a lot of it, I mean, and all in the service of some kind of connection with somebody else. But it starts, it seems, with trying to figure out a little bit more about yourself. Margaret, I’m curious what comes to mind for that.

Bagan: Well, I’m paid up on Bumble till the end of the month and then – truly, till the end of this month, and then I’m going to go off of it, and I’m going to try to meet someone out in the real world. I really am, because then it’s spring and it’s summer and I’ll be outside. And I’ve only been on it for three months, other than a couple of years ago, but I truly want to meet someone in person again because I’m just seeing that photos and texts just don’t match up when you meet face to face. So I want that to happen at the same time.

Miller: What’s your name?

Kate: Hi, I’m Kate. I have been on the sites and Bumble was supposed to be great, and it was not necessarily any better than anything else. It’s the weird, maybe generational, like my way of communicating who I am is not great on an app. I think there’s the added thing and kind of what I came in here a little bit with is as a 60-something person who’s actually still interested in the world of, in my case, heterosexual engagement. I don’t want to be married. I don’t want to necessarily live with someone, but that sharing cool stuff, it’s just part of, I think the question about what I’m looking for, raises curiosity about what even is the dating pool? And where are those super interesting, some shared experiences, men, in their mid-60s, who are not necessarily looking for someone younger, hotter, even though like, I’m super hot in my mid-60s. But, they’re not looking. And like that’s, maybe that’s the psychology question. Maybe it’s just like other folks in the generation, in the audience. But that’s kind of what I came in here with. It’s like, where are they? I’m sure they’re out there.

Miller: We’ve got a hand in the front here.

Eleanor: Hi there. My name’s Eleanor. So I’m a trans person, and the last time I like dating services and dating apps and things, I was trying to sort of figure out who I was. I was in the sort of midst of transition, and I used dating as a way of trying on different versions of myself. I would change my dating profile every four to six weeks, kind of radically, and it was hysterical. It was super fun. I’ve never learned more about myself from that process. And so, I’m not single right now and I was not expecting to comment, but your question, like I learned so much from dating through that process. So I wanted to reflect that to you.

Miller: I think we have time for two more comments.

Morgan: Hi, I’m Morgan. So once I turned 18, fortunately, this was pre-COVID, I spent two years intentionally using dating as a hobby, because I was aware of it, even then, it still took me a while to actually enter my first relationship. But I wanted to learn more about other people, and I wanted to learn more about the world through people’s perspectives and hobbies, and even more so, I wanted to learn about myself and my own preferences. And I learned so much. I learned about my own experience being neurodivergent and how long it takes for me to actually trust my intuition and learn if I’m actually attracted to the person or just really engaged in the conversation over the course of five dates and then realizing, oh, I don’t want anything to do with kissing you.

I learned about my preferences. For instance, I learned that I don’t like or I’m not looking to date tall men and I learned that after a date with a guy who is 6′7” and I felt like a hobbit the entire date. It was almost poetic what I was able to learn in terms of the depths of my preferences and also just how to engage with people. I’m so glad that it was before COVID cause I’m sure that it’s a hellscape now. I’m newly single and not looking forward to, I don’t think I’m going to jump onto the date or the dating apps, but I’d like made an entire inventory list, pre-COVID, of what I was looking for for each date or dating app, looked at it as an experiment. And I’m good with not going back onto those.

Armstrong: It’s an excellent point that both of you are bringing up that like, I really think like we cannot overstate enough. It’s because it’s really easy to fixate on the narrative around dating for ourselves and for, culturally, that it’s hard and it hurts and it’s exhausting, and it takes time and money and it’s hard and it’s hard and it’s hard, and it’s not working. It’s not working because I haven’t found this person. But dating in our current age, especially, is such a gift of opportunity for self-realization.

It’s like fertile soil, you get to learn about the world, you get to expand your knowledge of things and people and perspectives, like, trying to shift our mindset to like, dating is a social practice, is valuable. Finding the one and being partnered, these things are also valuable and be on your journey and do those things. But if we can shift our mindset of like, my ideal outcome for dating is to expand myself. That’s different than like, every single date I go on, every single match conversation I have, every single one of those things is a failure if it isn’t leading to that one person. And that’s not helpful. Then you’re just in a stew of failure and feeling bad about it, as opposed to like, yeah, dating is fun and I can learn about myself and expand. That’s a completely fantastic way to be going into dating. Thank you for sharing those things.

Miller: Sarah Ruby, Taylor, and Margaret, thank you all so much and thanks so much, everybody in this spirited audience. Thank you so much.

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