Dear Ally,
Thank you so much for joining me today on Tea For Two with Melanie Rose, where we pour a cup and dive into the most fascinating stories of creatives, designers, artisans, and educators like yourself.
Your resume, darling, is absolutely a "put the kettle on" situation—there's no way we're getting through this without a good brew.
Today, we're not just talking about where we travel, but who we become and how we love along the way.
They say travel is the only thing you buy that makes you richer, however my guest today believes the most profound "souvenirs" aren't the ones you can fold, pack, or squeeze into a suitcase. They're the ones that slip into your body, your boundaries, and your beliefs about what's possible in love.
Joining me is Ally Iseman, the visionary architect behind Passport 2 Pleasure. Over the last decade, Ally has been quietly but radically deconstructing the "default settings" of modern romance and replacing them with something far more adventurous. She's moved from the world of serial monogamy into becoming a premier community leader, guiding people through the often-uncharted territory of ethical non-monogamy, erotic freedom, and radical self-honesty.
Whether she's designing retreats, teaching workshops, or consulting one-on-one, Ally treats desire like a language people can actually learn, not a mystery they're doomed to misunderstand. But Ally doesn't just talk about these things in a classroom; she takes you right to the edge of the map. Through her work, she treats relational wellness not as a chore to be managed, but as a destination to be explored: integrating travel, play, and adventure into a "map of experiences" that gently, and sometimes provocatively, challenges everything we thought we knew about "happily ever after."
With Ally, your love life looks less like a checklist and more like a passport full of unexpected stamps.
Ally, I've been looking forward to this because you make the work of intimacy feel less like a therapy session and more like a first-class departure to a version of ourselves we haven't met yet.
Welcome to the show, darling.
You've spent years as a practitioner and educator, and you also wear the hat of writer and consultant. Was there a specific moment when you realized that your personal "un-learning" of relationship norms needed to become a public resource for others? Was it a conversation, a heartbreak, a client session—what was the spark?
For me, like so many, this all began as a personal journey unpacking the relational scripts that were no longer (if they had ever been) serving me. As I began exploring other ways of dating and relating, I also found myself exploring the rich world of play parties and other erotic events, diving deep into the uncharted territory of my own desires. This led me to start hosting events myself and helping grow communities in this area, a position that
found me inadvertently counseling and educating new explorers, individuals and couples alike, as they began collecting new stamps on their own passports to pleasure. Fast forward 7 years into my relation-trip as I call it, and I was stepping down from my in-house role as VP of Marketing at a growing brand. I knew I wanted to do something myself, something I cared about, something that lit me up and I felt would make a difference. And that’s when I realized I was already doing it, albeit informally and through referral only. I decided that pulling together my two decades of entertainment and marketing experience into a personal content brand and digital education platform, along with getting formally certified as a relationship coach, would make my resources available to a wider audience. My hope is that this would help continue to legitimize these conversations and ideally open up the wider discourse about what sexual and relational wellness really looks like in the modern age. It’s been a wild ride ever since launching Passport 2 Pleasure publicly in 2024. I truly believe that if we have better relationships that last longer, we’ll have a better world that lasts longer. Or, as I say in less polite company: If our world leaders were better fucked, we’d be less fucked.
Thank you so much for joining me today on Tea For Two with Melanie Rose, where we pour a cup and dive into the most fascinating stories of creatives, designers, artisans, and educators like yourself.
Your resume, darling, is absolutely a "put the kettle on" situation—there's no way we're getting through this without a good brew.
Today, we're not just talking about where we travel, but who we become and how we love along the way.
They say travel is the only thing you buy that makes you richer, however my guest today believes the most profound "souvenirs" aren't the ones you can fold, pack, or squeeze into a suitcase. They're the ones that slip into your body, your boundaries, and your beliefs about what's possible in love.
Joining me is Ally Iseman, the visionary architect behind Passport 2 Pleasure. Over the last decade, Ally has been quietly but radically deconstructing the "default settings" of modern romance and replacing them with something far more adventurous. She's moved from the world of serial monogamy into becoming a premier community leader, guiding people through the often-uncharted territory of ethical non-monogamy, erotic freedom, and radical self-honesty.
Whether she's designing retreats, teaching workshops, or consulting one-on-one, Ally treats desire like a language people can actually learn, not a mystery they're doomed to misunderstand. But Ally doesn't just talk about these things in a classroom; she takes you right to the edge of the map. Through her work, she treats relational wellness not as a chore to be managed, but as a destination to be explored: integrating travel, play, and adventure into a "map of experiences" that gently, and sometimes provocatively, challenges everything we thought we knew about "happily ever after."
With Ally, your love life looks less like a checklist and more like a passport full of unexpected stamps.
Ally, I've been looking forward to this because you make the work of intimacy feel less like a therapy session and more like a first-class departure to a version of ourselves we haven't met yet.
Welcome to the show, darling.
You've spent years as a practitioner and educator, and you also wear the hat of writer and consultant. Was there a specific moment when you realized that your personal "un-learning" of relationship norms needed to become a public resource for others? Was it a conversation, a heartbreak, a client session—what was the spark?
For me, like so many, this all began as a personal journey unpacking the relational scripts that were no longer (if they had ever been) serving me. As I began exploring other ways of dating and relating, I also found myself exploring the rich world of play parties and other erotic events, diving deep into the uncharted territory of my own desires. This led me to start hosting events myself and helping grow communities in this area, a position that
found me inadvertently counseling and educating new explorers, individuals and couples alike, as they began collecting new stamps on their own passports to pleasure. Fast forward 7 years into my relation-trip as I call it, and I was stepping down from my in-house role as VP of Marketing at a growing brand. I knew I wanted to do something myself, something I cared about, something that lit me up and I felt would make a difference. And that’s when I realized I was already doing it, albeit informally and through referral only. I decided that pulling together my two decades of entertainment and marketing experience into a personal content brand and digital education platform, along with getting formally certified as a relationship coach, would make my resources available to a wider audience. My hope is that this would help continue to legitimize these conversations and ideally open up the wider discourse about what sexual and relational wellness really looks like in the modern age. It’s been a wild ride ever since launching Passport 2 Pleasure publicly in 2024. I truly believe that if we have better relationships that last longer, we’ll have a better world that lasts longer. Or, as I say in less polite company: If our world leaders were better fucked, we’d be less fucked.
“Open up without blowing up" Your tagline, helping people "open up without blowing up," is so resonant. Looking back to your early days in 2016, was there a particular "near-explosion" in your own life that taught you the most about the necessity of relationship design? And if you're willing to share, what did repair look like after that moment?
The catalyst for me was experiencing the implosion of what ultimately became my last monogamous relationship in 2016. Let me preface by saying had I known then what I know now, I would have done A LOT differently. This is why I tell my clients: I’ve learned everything the hard way so they don’t have to! Back to an abridged version of “day zero.” Two years into our relation-trip, we had agreed to start exploring sexual connections outside of it within clear agreements. His opportunity came before mine and he operated within the parameters of our agreement, but they ended up staying up all night talking
with no play. Perfectly fine, it felt exciting to me! When my opportunity came, we agreed and I too operated within our agreement but ended up “seeing it through” and having a wonderful sexy night with my friend who was clear about the whole situation. It was such a confirming night that had opened up for me what I can only call “expansive love” – while my partner had not been physically present with me for the experience, he was deeply felt by me throughout and it added so much to my internal bond with him. I thought I had been loving my partners to the fullest extent of my potential up to this point in my life, but this experience showed me that there was so much more available. My boyfriend had requested that I call him when I was leaving and so I did, asking what he wanted to hear. I was gushing and radiating with love for him, telling him how close I felt to him, how grateful I was that we were exploring this together. And I was met with dead silence. And then all he said was, “I can’t believe you did it.” I’ll spare you the details, but over the next
two weeks our relationship fell apart, believe me there were many other issues at play as well that contributed. This experience was a symptom, not the causation. I will never know if he was “testing” me or if he had thought he would be okay with it and then was met with an onslaught of emotions he couldn’t manage, but either way, it wasn’t pretty. We both could have done a lot of things better. I learned that this was real for me, something I didn’t understand and wanted to explore, so I made the decision to do so on my own to avoid any further emotional casualties on my conscience. It doesn’t have to unfold like that, and I’ve witnessed and been a part of seeing how many wonderful ways people can open up, and so I’ve dedicated my work to helping people navigate these transitions, mitigating as much risk and unintended consequences as possible.
The catalyst for me was experiencing the implosion of what ultimately became my last monogamous relationship in 2016. Let me preface by saying had I known then what I know now, I would have done A LOT differently. This is why I tell my clients: I’ve learned everything the hard way so they don’t have to! Back to an abridged version of “day zero.” Two years into our relation-trip, we had agreed to start exploring sexual connections outside of it within clear agreements. His opportunity came before mine and he operated within the parameters of our agreement, but they ended up staying up all night talking
with no play. Perfectly fine, it felt exciting to me! When my opportunity came, we agreed and I too operated within our agreement but ended up “seeing it through” and having a wonderful sexy night with my friend who was clear about the whole situation. It was such a confirming night that had opened up for me what I can only call “expansive love” – while my partner had not been physically present with me for the experience, he was deeply felt by me throughout and it added so much to my internal bond with him. I thought I had been loving my partners to the fullest extent of my potential up to this point in my life, but this experience showed me that there was so much more available. My boyfriend had requested that I call him when I was leaving and so I did, asking what he wanted to hear. I was gushing and radiating with love for him, telling him how close I felt to him, how grateful I was that we were exploring this together. And I was met with dead silence. And then all he said was, “I can’t believe you did it.” I’ll spare you the details, but over the next
two weeks our relationship fell apart, believe me there were many other issues at play as well that contributed. This experience was a symptom, not the causation. I will never know if he was “testing” me or if he had thought he would be okay with it and then was met with an onslaught of emotions he couldn’t manage, but either way, it wasn’t pretty. We both could have done a lot of things better. I learned that this was real for me, something I didn’t understand and wanted to explore, so I made the decision to do so on my own to avoid any further emotional casualties on my conscience. It doesn’t have to unfold like that, and I’ve witnessed and been a part of seeing how many wonderful ways people can open up, and so I’ve dedicated my work to helping people navigate these transitions, mitigating as much risk and unintended consequences as possible.
You've been featured in everything from The New York Times to Cosmopolitan. When you're speaking to such a broad audience, what is the one myth about non-monogamy that you feel most protective of debunking? Is there a misconception you wish you could gently retire from the headlines forever?
It’s this two-hander: that consensual or ethical non-monogamy is not “a phase” synonymous with casual dating and that it’s not all about sex (sometimes it can be, just like monogamous dating, and that’s okay too when everyone is clear and on the same page).
Trying to open your last monogamous relationship didn't go the way you hoped. Looking back, what did that experience, gently or not so gently, teach you about desire versus readiness? For listeners who might be in that "we're curious, but we're not sure" phase, what do you wish they knew?
The discrepancy between desire and preparedness is one of the biggest gaps I see causing so much unnecessary turmoil right out the gate. Being curious about something is not the same thing as being knowledgeable about it, but it can be a great motivator to learn more. People who are curious to explore ENM often think the first conversation to have with their partner is about “convincing” or “persuading” them that it’s a good idea. Great recipe for a fight and to create division in your partnership. If this truly is a “we” thing (because exploring on your own is not the same thing as exploring with a partner) then your first conversation is about understanding where your partner is coming from. Have they even heard the term ENM or open relationship before? What do they think about it? I’m willing to bet they’ve heard all the same misinformation you have and that’s the filter that they’re going to hear you through. Step one is: educate yourself. Being curious is one thing, but do you even really understand the thing you’re curious about, or WHY you’re even curious about it in the first place? (I created a free tool to help people understand their Big Why for exploring ENM: www.passport2pleasure.com/bigwhy) Once you’ve satisfied your curiosity for your own motivations, and educated yourself to better understand what it even is you want to explore, now it’s time to get curious about your partner. Invite them into the experience with you. Maybe there’s an article you saw or a film you heard about and you’re wondering if they've ever heard the term ENM? What do they know about it? Would they be interested in reading that article or watching that film together and then talking about it? If you realize you’re curious to swim, you don’t just go jump into the Pacific Ocean, first you educate yourself, get the right equipment, and take lessons at the local pool. This isn’t a destination you get to, it’s an ongoing conversation, that’s why I call it a relation-trip.
So let's talk about play, safety, and sanctuaries. You've gone from participant to leader in these spaces. Do you remember what it felt like to walk into your first curated play party? What shifted for you in how you understood consent, safety, or intimacy in that moment?
I will never forget my first play party. It was equally confirming as my fun sexy night with my friend from my monogamy blow up story. I had managed to get an introduction to this community through one of the app dates I had been on, a delicious afternoon delight (I was deeply into my new “try everything once” era, don’t think I’ve ever stopped). Since I was new and not really talking about this with anyone in my life, I didn’t have anyone to go with, so I decided to go on my own. It was being held at a penthouse suite in a fancy hotel in West LA. When the play partners who were hosting the party found out it was my first, they were thrilled and took me under their wing, introducing me to everyone and giving me the run down. Later on in the evening, after meeting a lot of lovely people whilst classy pornography played on large screens in the background, I noticed it had cleared out quite a bit. It was earlier for that than I would have thought and I hadn’t seen much play, so I noted this to the lovely host. She quickly smiled, took me by the arm, and said, “come with me.” She led me around a corner down a short hallway I hadn’t even noticed which opened up into what I can only call the orgy room. I stood transfixed in the doorway, rooted so deeply in my body, all I could do was breathe. It was like witnessing a live Renaissance painting, bodies of all types undulating in rhythm, I was riveted. All of a sudden this deep inner voice resonated within me, “You are safe, there are others like you, you are home.”
It’s this two-hander: that consensual or ethical non-monogamy is not “a phase” synonymous with casual dating and that it’s not all about sex (sometimes it can be, just like monogamous dating, and that’s okay too when everyone is clear and on the same page).
Trying to open your last monogamous relationship didn't go the way you hoped. Looking back, what did that experience, gently or not so gently, teach you about desire versus readiness? For listeners who might be in that "we're curious, but we're not sure" phase, what do you wish they knew?
The discrepancy between desire and preparedness is one of the biggest gaps I see causing so much unnecessary turmoil right out the gate. Being curious about something is not the same thing as being knowledgeable about it, but it can be a great motivator to learn more. People who are curious to explore ENM often think the first conversation to have with their partner is about “convincing” or “persuading” them that it’s a good idea. Great recipe for a fight and to create division in your partnership. If this truly is a “we” thing (because exploring on your own is not the same thing as exploring with a partner) then your first conversation is about understanding where your partner is coming from. Have they even heard the term ENM or open relationship before? What do they think about it? I’m willing to bet they’ve heard all the same misinformation you have and that’s the filter that they’re going to hear you through. Step one is: educate yourself. Being curious is one thing, but do you even really understand the thing you’re curious about, or WHY you’re even curious about it in the first place? (I created a free tool to help people understand their Big Why for exploring ENM: www.passport2pleasure.com/bigwhy) Once you’ve satisfied your curiosity for your own motivations, and educated yourself to better understand what it even is you want to explore, now it’s time to get curious about your partner. Invite them into the experience with you. Maybe there’s an article you saw or a film you heard about and you’re wondering if they've ever heard the term ENM? What do they know about it? Would they be interested in reading that article or watching that film together and then talking about it? If you realize you’re curious to swim, you don’t just go jump into the Pacific Ocean, first you educate yourself, get the right equipment, and take lessons at the local pool. This isn’t a destination you get to, it’s an ongoing conversation, that’s why I call it a relation-trip.
So let's talk about play, safety, and sanctuaries. You've gone from participant to leader in these spaces. Do you remember what it felt like to walk into your first curated play party? What shifted for you in how you understood consent, safety, or intimacy in that moment?
I will never forget my first play party. It was equally confirming as my fun sexy night with my friend from my monogamy blow up story. I had managed to get an introduction to this community through one of the app dates I had been on, a delicious afternoon delight (I was deeply into my new “try everything once” era, don’t think I’ve ever stopped). Since I was new and not really talking about this with anyone in my life, I didn’t have anyone to go with, so I decided to go on my own. It was being held at a penthouse suite in a fancy hotel in West LA. When the play partners who were hosting the party found out it was my first, they were thrilled and took me under their wing, introducing me to everyone and giving me the run down. Later on in the evening, after meeting a lot of lovely people whilst classy pornography played on large screens in the background, I noticed it had cleared out quite a bit. It was earlier for that than I would have thought and I hadn’t seen much play, so I noted this to the lovely host. She quickly smiled, took me by the arm, and said, “come with me.” She led me around a corner down a short hallway I hadn’t even noticed which opened up into what I can only call the orgy room. I stood transfixed in the doorway, rooted so deeply in my body, all I could do was breathe. It was like witnessing a live Renaissance painting, bodies of all types undulating in rhythm, I was riveted. All of a sudden this deep inner voice resonated within me, “You are safe, there are others like you, you are home.”
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As you moved from participant to leader, how did your relationship to these spaces, and to your own boundaries, change?
Shifting from guest to staff to leader and organizer and now educator and facilitator, these roles all come with their own power dynamics in different settings and circumstances. It has taught me SO much about power and responsibility, boundaries and respect. As one example: when I am hosting or facilitating, I do not play at that event and I do not approach anyone. I am open to people approaching me and asking if we can connect at another time. I also explicitly state this to guests at the event and in any pre-event materials that I have control over. This helps honor what I consider important boundaries and the impact of power dynamics on consent.
You've described play environments as feeling like a "vacation from reality." What do you think allows people to show up more freely there than they often do in everyday life? And how do you help them bring a little bit of that freedom back into their "normal" lives without blowing everything up?
Shame is used to control people in much of the world. These spaces are shameless by design. Erotic events and pleasure-positive communities are led by curiosity and shaped with mutual celebration. Shame is one of the most useless emotions to feel within yourself as it is more about someone else’s perspective than your own reality. When you learn to understand, accept, and then celebrate the things within yourself which you have been taught to feel shame around, you can start to feel untouchable. This is easier to do when it’s being modeled all around you. You thought that one kinky thing you were always curious about was so crazy?! It won’t take long for you to see things far beyond that you’ve never even dreamed of. And everyone involved is having a great time doing it. This is the power of pleasure-positivity in a pleasure-negative world. Without the stranglehold of shame limiting how you speak and show up in the world, you become empowered in a deep felt sense of self knowledge, and that’s something no one can touch. I don’t have any shame about any corner of myself. Even things I wish I had done differently in the past are not held as regrets because I created value in learning from them. If I have nothing to hide, I don’t have a control mechanism that someone else can activate. I encourage people to bring these experiences out into their “real” lives by building pleasure-led practices in their every day, and that is by no means limited to sexual activities. I love and celebrate who I am and how I create pleasure in all areas of my life, and I want that empowered experience for everyone. Harness your sensual empowerment and watch every area of your life open up exponentially, from the bedroom to the boardroom!
I love the name Passport 2 Pleasure. Was there a moment when it clicked for you that travel and relational wellness were deeply connected? Was there a particular journey or destination that first made you think, "Oh, this is more than a holiday, this is a relational reset"?
It was more of an esoteric realization than a particular lived experience as I am a deeply reflective and thoughtful person by nature. I got to thinking about how people refer to growth as a “journey” yet often personal and relational growth is met with resistance. It’s seen as work, another task, something else that takes more effort loaded onto an already maxed out schedule. The unknown is seen as a risk, dangerous and uncomfortable territory to be avoided at all costs. Yet when that same unknown is taken out into the world in the form of a vacation or unknown adventure, there couldn’t be more excitement and
anticipation. I want people to have the same experience with their internal journey as their outer one. This relationship we all covet is often seen as the finish line, a destination we get to when we’re ready, we’ve worked on ourselves enough, and we “deserve” it. But it’s not a destination. Think about it, Disney movies, fairy tales, and romcoms all end at the beginning of the relationship. It’s not one happily ever after, a relationship is an ongoing conversation. There are a variety of stops and experiences along the way shaping it and adding skills to your relationship toolbelt. Like stamps on a passport. That’s why I call it a relation-trip.
You intentionally avoid telling people how their relationships "should" look. Why is creating space for self-discovery more important to you than giving advice?
I don’t tell people what their relationships should look like because “should” is usually inherited, not chosen, and I wouldn’t want anyone “shouldering” all over themselves. Most of us are running unconscious scripts. Monogamy by default. Marriage as a milestone. Jealousy as proof of love. We didn’t design those; we were prescribed them. So when someone comes to me asking, “Should we open?” or “Should I stay monogamous?” my job isn’t to hand them a template. It’s to help them uncover what’s actually true for them. Advice creates compliance. Self-discovery creates ownership. And self ownership is what sustains a relationship when things get hard. When you design your relationship around your real emotional and sexual needs, your values, your capacity, your desires, you don’t feel like you’re performing someone else’s blueprint. You feel aligned. That alignment is far more durable than following expert instructions. That’s why I built my free Relationship Style Quiz. It’s based on my exclusivity quadrant model, which maps emotional/romantic and physical/sexual needs separately. Most people have never been invited to look at those as distinct dimensions. Once you see within which of the 4 Relationship Styles you naturally fall, you can explore what types of relationship structures might actually support you, instead of trying to squeeze yourself into one that doesn’t just because you’ve been told you “should.” If you’re curious about your own relationship style, you can take my free quiz at www.myrelationshipstyle.com. My work isn’t about telling people how to love. It’s about giving them the tools and language to consciously choose how they want to.
Shifting from guest to staff to leader and organizer and now educator and facilitator, these roles all come with their own power dynamics in different settings and circumstances. It has taught me SO much about power and responsibility, boundaries and respect. As one example: when I am hosting or facilitating, I do not play at that event and I do not approach anyone. I am open to people approaching me and asking if we can connect at another time. I also explicitly state this to guests at the event and in any pre-event materials that I have control over. This helps honor what I consider important boundaries and the impact of power dynamics on consent.
You've described play environments as feeling like a "vacation from reality." What do you think allows people to show up more freely there than they often do in everyday life? And how do you help them bring a little bit of that freedom back into their "normal" lives without blowing everything up?
Shame is used to control people in much of the world. These spaces are shameless by design. Erotic events and pleasure-positive communities are led by curiosity and shaped with mutual celebration. Shame is one of the most useless emotions to feel within yourself as it is more about someone else’s perspective than your own reality. When you learn to understand, accept, and then celebrate the things within yourself which you have been taught to feel shame around, you can start to feel untouchable. This is easier to do when it’s being modeled all around you. You thought that one kinky thing you were always curious about was so crazy?! It won’t take long for you to see things far beyond that you’ve never even dreamed of. And everyone involved is having a great time doing it. This is the power of pleasure-positivity in a pleasure-negative world. Without the stranglehold of shame limiting how you speak and show up in the world, you become empowered in a deep felt sense of self knowledge, and that’s something no one can touch. I don’t have any shame about any corner of myself. Even things I wish I had done differently in the past are not held as regrets because I created value in learning from them. If I have nothing to hide, I don’t have a control mechanism that someone else can activate. I encourage people to bring these experiences out into their “real” lives by building pleasure-led practices in their every day, and that is by no means limited to sexual activities. I love and celebrate who I am and how I create pleasure in all areas of my life, and I want that empowered experience for everyone. Harness your sensual empowerment and watch every area of your life open up exponentially, from the bedroom to the boardroom!
I love the name Passport 2 Pleasure. Was there a moment when it clicked for you that travel and relational wellness were deeply connected? Was there a particular journey or destination that first made you think, "Oh, this is more than a holiday, this is a relational reset"?
It was more of an esoteric realization than a particular lived experience as I am a deeply reflective and thoughtful person by nature. I got to thinking about how people refer to growth as a “journey” yet often personal and relational growth is met with resistance. It’s seen as work, another task, something else that takes more effort loaded onto an already maxed out schedule. The unknown is seen as a risk, dangerous and uncomfortable territory to be avoided at all costs. Yet when that same unknown is taken out into the world in the form of a vacation or unknown adventure, there couldn’t be more excitement and
anticipation. I want people to have the same experience with their internal journey as their outer one. This relationship we all covet is often seen as the finish line, a destination we get to when we’re ready, we’ve worked on ourselves enough, and we “deserve” it. But it’s not a destination. Think about it, Disney movies, fairy tales, and romcoms all end at the beginning of the relationship. It’s not one happily ever after, a relationship is an ongoing conversation. There are a variety of stops and experiences along the way shaping it and adding skills to your relationship toolbelt. Like stamps on a passport. That’s why I call it a relation-trip.
You intentionally avoid telling people how their relationships "should" look. Why is creating space for self-discovery more important to you than giving advice?
I don’t tell people what their relationships should look like because “should” is usually inherited, not chosen, and I wouldn’t want anyone “shouldering” all over themselves. Most of us are running unconscious scripts. Monogamy by default. Marriage as a milestone. Jealousy as proof of love. We didn’t design those; we were prescribed them. So when someone comes to me asking, “Should we open?” or “Should I stay monogamous?” my job isn’t to hand them a template. It’s to help them uncover what’s actually true for them. Advice creates compliance. Self-discovery creates ownership. And self ownership is what sustains a relationship when things get hard. When you design your relationship around your real emotional and sexual needs, your values, your capacity, your desires, you don’t feel like you’re performing someone else’s blueprint. You feel aligned. That alignment is far more durable than following expert instructions. That’s why I built my free Relationship Style Quiz. It’s based on my exclusivity quadrant model, which maps emotional/romantic and physical/sexual needs separately. Most people have never been invited to look at those as distinct dimensions. Once you see within which of the 4 Relationship Styles you naturally fall, you can explore what types of relationship structures might actually support you, instead of trying to squeeze yourself into one that doesn’t just because you’ve been told you “should.” If you’re curious about your own relationship style, you can take my free quiz at www.myrelationshipstyle.com. My work isn’t about telling people how to love. It’s about giving them the tools and language to consciously choose how they want to.
You often say relationships aren't something we "arrive at," but something we continually shape. How has this perspective changed the way you love? Has it changed the way you handle conflict, or endings, or even commitment?
I see endings more as transitions now, and definitely not as failures. As long as it was a net- positive experience and we’re both better off for having known each other in that context, ideally having learned something about ourselves and from each other, that’s a major success in my book! Love is not a zero sum game, approaching it like that greatly limited how it showed up in my life. Approaching it expansively and from a place of curiosity has led me to have far more deeply enriching relationships of all kinds, from platonic to romantic, casual to committed.
When people finish a course or a session with you, they've learned the skills. But what is the feeling you hope they carry with them when they close their laptop or leave the event? If you could bottle that feeling and label it like a perfume or a candle, what would you call it?
Curiosi-tea, of course.
Ally, if the 2016 version of you walked into your office today, what is the one piece of Passport 2 Pleasure wisdom that would have most surprised her? And do you think she would have believed you?
I would invite her to understand that “trying to make something work” is not the same thing as creating something that does. She used to think that the most important thing was making a relationship work, at the expense of herself, her joy, her pleasure, and her growth. She would have never believed that she could be in a relationship that was so secure she could actively choose to work with and play in erotic jealousy safely with a partner, let alone have a community of friends who live and love in expansive ways like she does, even if it doesn’t look exactly like it does for her.
I see endings more as transitions now, and definitely not as failures. As long as it was a net- positive experience and we’re both better off for having known each other in that context, ideally having learned something about ourselves and from each other, that’s a major success in my book! Love is not a zero sum game, approaching it like that greatly limited how it showed up in my life. Approaching it expansively and from a place of curiosity has led me to have far more deeply enriching relationships of all kinds, from platonic to romantic, casual to committed.
When people finish a course or a session with you, they've learned the skills. But what is the feeling you hope they carry with them when they close their laptop or leave the event? If you could bottle that feeling and label it like a perfume or a candle, what would you call it?
Curiosi-tea, of course.
Ally, if the 2016 version of you walked into your office today, what is the one piece of Passport 2 Pleasure wisdom that would have most surprised her? And do you think she would have believed you?
I would invite her to understand that “trying to make something work” is not the same thing as creating something that does. She used to think that the most important thing was making a relationship work, at the expense of herself, her joy, her pleasure, and her growth. She would have never believed that she could be in a relationship that was so secure she could actively choose to work with and play in erotic jealousy safely with a partner, let alone have a community of friends who live and love in expansive ways like she does, even if it doesn’t look exactly like it does for her.
RAPID-FIRE ROUND
This is a first for me: rapid-fire questions. Think of it as a little lightning round for your relational carry-on. The ultimate relational souvenir: would you say it's a shared memory, a new skill, or a physical object?
Our relation-trips are merely passports filled with stamps of shared memories, so that will have to be my answer.
Window or aisle? And does that choice say anything about your personality in bed?
If I’m traveling solo, I grab that window so I can see the sights and take a nap easily if I need to. A little restraint doesn’t make me claustrophobic, quite the opposite. Besides, I never mind crawling over top of someone to get what I want…in this case, the bathroom.
Carry-on only or checked bags? In other words, do you prefer minimalist connection, or do you like to bring all the emotional "luggage" to the table?
It really depends on the trip. I like to feel prepared, but I’m a wilderness backpacker so I prefer to travel minimal and light. Better for flexibility.
Jet lag or heartbreak: which is harder to recover from?
Jet lag – time is a construct but damn is her zoning impactful! Heartbreak is the bittersweet nectar of life, it lets me know I’ve loved. And what a privilege that is.
Your next destination: where, physically or relationally, is Ally Isleman headed next?
I am in the midst of moving my base from Los Angeles to London. That looks like packing up my house in Santa Monica to be rented out and renegotiating what long distance looks like with my LA girlfriend of 1.5 years (we’ve known each since pre-pandemic times). That also looks like relying heavily on my London bf to sort out our new home as I await my visa approvals (we’ve been dating for just shy of a year and a half and are now moving in
together).
Room service or local street food: what's your style when it comes to novelty in relationships?
Room service is great after a good long sex session – aftercare FTW! – but I love the culinary adventure of trying all the best-plant based cuisine anywhere I am in the world! I have lived a consent-based (vegan) lifestyle since 2006: I don’t eat or put anyone in my mouth without their explicit permission.
Darling, I'm sure you knew this was coming. You've been residing in my old home town, London, for the last several months, so it's only fair to ask: have you found your tea yet? I’ve chosen three which, I think, you might like.
English Breakfast Tea. Bold, rich, and comforting, it's the classic British morning tea, usually taken with milk (and sometimes sugar). Think cozy kitchens and rainy mornings.
Earl Grey. Black tea scented with bergamot citrus. It's fragrant, slightly floral, and a touch elegant. It’s giving very afternoon tea vibes. Lovely plain or with a splash of milk.
Yorkshire Tea. A much-loved everyday British blend, especially in the north of England. Strong, smooth, and made to stand up to milk. If you want something authentically British, this is it.
So, Ally, when it comes to love and adventure, are you English Breakfast, Earl Grey, or Yorkshire Tea?
I’ve only yet tried two of the three, so I must add Yorkshire Tea to my liquid longing list. I’m a bougie bitch and so I love a little something extra like the bergamot twist in Earl Grey. Though I have discovered whilst on this rainy island: not all Earl Greys are created equally. Thus continues my exploration of all 50 shades…
Milk? Yes or No
Generally only with black tea, and depending on which one: oat or almond.
Sugar? Yes or No
My boisterous sweet tooth is reserved solely for high quality desserts and unique pastries. I would rather eat my sweets than drink them.
This is a first for me: rapid-fire questions. Think of it as a little lightning round for your relational carry-on. The ultimate relational souvenir: would you say it's a shared memory, a new skill, or a physical object?
Our relation-trips are merely passports filled with stamps of shared memories, so that will have to be my answer.
Window or aisle? And does that choice say anything about your personality in bed?
If I’m traveling solo, I grab that window so I can see the sights and take a nap easily if I need to. A little restraint doesn’t make me claustrophobic, quite the opposite. Besides, I never mind crawling over top of someone to get what I want…in this case, the bathroom.
Carry-on only or checked bags? In other words, do you prefer minimalist connection, or do you like to bring all the emotional "luggage" to the table?
It really depends on the trip. I like to feel prepared, but I’m a wilderness backpacker so I prefer to travel minimal and light. Better for flexibility.
Jet lag or heartbreak: which is harder to recover from?
Jet lag – time is a construct but damn is her zoning impactful! Heartbreak is the bittersweet nectar of life, it lets me know I’ve loved. And what a privilege that is.
Your next destination: where, physically or relationally, is Ally Isleman headed next?
I am in the midst of moving my base from Los Angeles to London. That looks like packing up my house in Santa Monica to be rented out and renegotiating what long distance looks like with my LA girlfriend of 1.5 years (we’ve known each since pre-pandemic times). That also looks like relying heavily on my London bf to sort out our new home as I await my visa approvals (we’ve been dating for just shy of a year and a half and are now moving in
together).
Room service or local street food: what's your style when it comes to novelty in relationships?
Room service is great after a good long sex session – aftercare FTW! – but I love the culinary adventure of trying all the best-plant based cuisine anywhere I am in the world! I have lived a consent-based (vegan) lifestyle since 2006: I don’t eat or put anyone in my mouth without their explicit permission.
Darling, I'm sure you knew this was coming. You've been residing in my old home town, London, for the last several months, so it's only fair to ask: have you found your tea yet? I’ve chosen three which, I think, you might like.
English Breakfast Tea. Bold, rich, and comforting, it's the classic British morning tea, usually taken with milk (and sometimes sugar). Think cozy kitchens and rainy mornings.
Earl Grey. Black tea scented with bergamot citrus. It's fragrant, slightly floral, and a touch elegant. It’s giving very afternoon tea vibes. Lovely plain or with a splash of milk.
Yorkshire Tea. A much-loved everyday British blend, especially in the north of England. Strong, smooth, and made to stand up to milk. If you want something authentically British, this is it.
So, Ally, when it comes to love and adventure, are you English Breakfast, Earl Grey, or Yorkshire Tea?
I’ve only yet tried two of the three, so I must add Yorkshire Tea to my liquid longing list. I’m a bougie bitch and so I love a little something extra like the bergamot twist in Earl Grey. Though I have discovered whilst on this rainy island: not all Earl Greys are created equally. Thus continues my exploration of all 50 shades…
Milk? Yes or No
Generally only with black tea, and depending on which one: oat or almond.
Sugar? Yes or No
My boisterous sweet tooth is reserved solely for high quality desserts and unique pastries. I would rather eat my sweets than drink them.
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Ingredients:
1 cup water
1 teaspoon loose Earl Grey tea or 1 tea bag
A small strip of fresh bergamot peel (or substitute: orange + a little lemon zest)
Honey or sugar (optional)
Milk (optional)
Instructions:
Bring the water to a boil, then let it cool for about 30 seconds (ideal temp: just under boiling).
Add the Earl Grey tea to your cup or teapot.
Drop in the fresh bergamot peel (this intensifies the signature citrus aroma).
Pour the hot water over the tea and steep for 3–5 minutes.
Remove the tea leaves/bag and peel.
Sweeten with honey or sugar if you like, and add a splash of milk if desired.
Extra twist ideas:
Add a drop of vanilla extract for a creamy “London Fog” vibe
Try a slice of fresh ginger for warmth
Serve iced with a squeeze of lemon for a refreshing version
