A Conversation with Dr. Jess O’Reilly: Modern Intimacy, Desire & Feminine Power
A deep-dive into emotional literacy, relationship dynamics, confidence and how women can cultivate connection without performance pressure with sex and relationship expert
By: The Lace Ledger Staff
Intimacy has long been dressed in expectation. For generations, women were handed scripts about desire that prized accommodation over appetite and harmony over honesty. What is shifting now is not simply how we speak about sex, but how we inhabit it.
In this conversation, Dr. Jess O’Reilly invites us to look at intimacy as something cultivated, deeply tied to emotional literacy. What emerges is a recalibration—one that reframes feminine power not as perfection, but presence.
When you look back at the messages women were taught about intimacy, desire and femininity even a generation ago, what do you think we are still carrying — consciously or unconsciously — into our relationships today?
Pressure to perform still exists on so many levels.
When it comes to sexual desire, for example, we feel pressure to “have it”. We’re told that we’re broken or something is awry if we don’t experience spontaneous desire rather than recognizing that:
a. Sexual desire fluctuates greatly between individuals and across the lifespan.
b. Sexual desire can be cultivated; it doesn’t have to show up on its own.
We also experience pressure to be accommodating, likeable, flexible and emotionally attuned to others. Of course, there is value in embodying these behaviours or traits, but not when it’s to our own detriment or at the cost of deprioritizing our own needs. Even when we consciously reject those scripts, they often show up unconsciously through guilt around saying no, pressure to be desirable rather than desiring, or the belief that relational harmony requires self-erasure.
With regard to intimacy, we often see it as unique to romantic or sexual relationships; but we are seeing a shift to recognize that we can be intimate in so many different ways and in many types of relationships including friendships.
When we talk about femininity being “rewritten,” where do you see the most meaningful shifts happening right now?
One significant shift certainly involves role flexibility. Femininity is no longer tied to a narrow set of behaviours, timelines, or relational scripts. There is more room to define how show up at work, in relationships, as parents, and in the bedroom. The idea is that we can find ways that feel personally meaningful rather than prescribed - of course, this isn’t always the outcome and some folks have more privilege to push boundaries when it comes to roles. Choice comes with privilege.
Having said that, this expansion can come with added pressure. When there are more options, there can be an unspoken expectation to do femininity “well” and the checklist can just get longer and longer. Do we always have to be empowered, sexually confident, emotionally available and self-actualized? Is there really more flexibility if we don’t really have the option to opt out a rest and not constantly be optimizing ourselves?
How have modern expectations around femininity changed the way people experience desire and intimacy in their day-to-day lives?
Modern expectations have expanded the conversation about desire and intimacy, but they have also intensified self-monitoring and pressure. We often feel pressure to be sexually confident, emotionally literate, communicative and self-aware at all times. Desire becomes something we evaluate and manage rather than something we experience in varying ways.
We may find ourselves asking whether desire is showing up in the right way or with the right intensity. But desire is highly contextual. It responds to stress, safety, fatigue, health, relationship dynamics and power. Performance pressure can detract from desire and intimacy and move these experiences away from presence into a space of expectation.
On the positive side, many folks now have more language for desire and intimacy, which can be deeply affirming. When used with flexibility rather than pressure, it allows us to name what we want, recognize what feels good — emotionally, physically, relationally, spiritually, erotically. And if makes space for us to experience pleasure and intimacy as evolving.
In your work, where do people most often confuse intimacy with obligation, especially in long-term relationships?
Intimacy is sometimes confused with access especially in long-term relationships. Emotional closeness or commitment can start to feel like entitlement to sex, emotional labour, reassurance or availability on demand. But intimacy isn’t something we are entitled to because we’re in a relationship for a specific period of time.
Every interaction and every dynamic requires that we opt in. Role fulfilment and pressure can really create unrealistic expectations. We make assumptions that a partner ought to be available in a specific way rather than cultivating consent. This doesn’t just apply to sex, but also to care, emotional labour, mental labour and more. When we impose expectations of care or connection, we’re often missing curiosity and true respect. And all of these relational elements need to be cultivated; they’re not automatically bestowed.
How does emotional literacy — or the lack of it — shape the way people navigate sex, conflict and connection?
Emotional literacy really lays the groundwork for connection, sex, pleasure, relationships and every human interaction because every interaction — from the mundane to the intimate — is an emotional one. It doesn’t matter if you’re having a one night stand or making love to someone you consider your soulmate — all interactions involve feelings.
With emotional literacy, we are better equipped to stay present with discomfort, express needs without blame and respond to their partner rather than react to our own fears. This doesn’t eliminate conflict or vulnerability, but it does make connection more resilient and sex more grounded in mutual awareness rather than guesswork.
What role does self-intimacy play in sustaining healthy romantic and relational intimacy over time?
Self-intimacy often involves the ability to stay connected to your own experience. When it comes to self-pleasure, this may involve your own sensations, desires, feelings and fantasies.
More generally, this might involve awareness of your emotions, limits, values and capacity. And this connection to self — whether in the bedroom or in the living room — allows you to stay connected without outsourcing your needs to a partner.
When it comes to pleasure, we often turn to a partner with expectations that they understand our needs intuitively. Or we expect them to create pleasure in our bodies without knowing how to do so ourselves. Of course, you can enjoy being curious and exploratory together, but it can be just as fulfilling to do so on your own. And the benefits of knowing your own body, needs, desires and boundaries flows into the relationship, as you’ll likely be better equipped to express needs clearly, tolerate difference and engage in connection from a place of choice rather than depletion.
What misconceptions about desire do you most wish people would let go of as they age or move through different life stages?
The biggest misconception is that desire should show up spontaneously and consistently across time. Many people experience responsive desire, meaning desire emerges after connection, touch, or erotic context.
As bodies, hormones, health, stress levels and identities shift, desire often changes form rather than disappearing. When people interpret this change as failure, they stop engaging with desire altogether.
Desire doesn’t necessarily vanish with age or life transitions, but it needs to be approached differently. Not only can our definitions of pleasure and the erotic expand over time, but our triggers for desire also evolve. If we treat a change as problematic, we may miss out on the potential for expanding our repertoire which comes with curiosity.
For those navigating open, evolving, or non-traditional relationship structures, what foundations matter more than rules?
Regardless of whether you’re monogamous or ethically non-monogamous, care, respect, communication and curiosity are of paramount importance. We often think that the framework or arrangement determines the outcome in relationships, but research suggests otherwise. The foundations are similar and might include emotional regulation, self awareness, repair skills, the capacity to manage discomfort and general kindness and commitment. Rules can provide some clarity, but if you struggle with avoidance, communication or accountability, no set of rules (whether you’re monogamous or ENM) are going to fill the gap.
Relationships that grow successfully are built on consent and commitment as ongoing practices as opposed to one-time agreements.
If intimacy today is less about perfection and more about presence, what practices help people stay connected to themselves and each other?
From a practical perspective, disconnecting from our devices to reduce technoference can make a world of difference. Even brief, intentional pockets of undistracted time help people feel seen and prioritized. And so much scrolling can drain us emotionally, with psychogenic symptoms showing up in the body. It’s hard to transition to connection and pleasure after engaging with heartbreaking and exhausting news all day long in the palm of our hands.
Physically, slowing down matters. This can mean taking more time with touch, pausing before responding or allowing moments of quiet without rushing to fill them. Slowness can increase awareness and help you to discover new ways to express and receive pleasure.
In terms of approach, letting go of specific outcomes is key. When intimacy is treated as something that must lead to a specific experience (e.g. orgasm, resolution, reassurance), we tend to perform rather than connect. Shifting the focus from goals to experience can alleviate pressure and heighten pleasure.
And finally, making space for ongoing check-ins helps intimacy stay responsive. Asking simple questions like “How are you feeling right now?” or “What would feel supportive in this moment?” keeps connection dynamic rather than assumed. Presence can’t begin or end in the bedroom. Sometimes people note that they have trouble staying in the moment in bed, so we start by looking at how we move through life all day long; it makes sense that if we move through meals, work, commutes and habits mindlessly that we may be inclined to do the same thing in bed.
As femininity continues to be rewritten, what do you hope intimacy looks like for women in the next decade — not just in partnership, but in how they relate to themselves?
I hope intimacy becomes more accessible — to everyone. It’s related to joy, ease, rest, comfort, care and safety and so many people don’t have access to these basic needs. Shame, stigma, judgment and pressure all distract from our experiences of intimacy and pleasure, so part of an ideal future would involve their dismantlement.
And this isn’t an individual or coupled process. Shame is systemic. It’s tied to oppression, greed, imperialism and control. So it’s not a matter of a single movement that will destroy it. The process has to be entirely about liberation and it’s hard to feel hopeful at this moment in time. But there are glimmers. So many people hold space for joy and nuance even in grief. I hope that intimacy and pleasure feel like experiences we’re allowed to embrace in our bodies, in our relationships and in our everyday lives.
When it comes to sex, I hope we have fewer hangups. I hope we can do what feels good and not have to perform (unless we’re into that!). One positive shift I see is an increase in sexual communication across generations and cultures, so I’m hopeful that bringing sex from the backroom to the living room will create more openings for pleasure for everyone.
What lingers after this conversation is a mindset shift to treat intimacy as something practiced (not presumed), something rooted in consent and desire rather than entitlement, expectation or role fulfillment. If desire is contextual and connection is cultivated, then feminine power no longer hinges on performing confidence or sustaining perfection: it lives in awareness, in the courage to opt in deliberately.
To rewrite intimacy is to loosen the grip of shame and make room for slow, sacred presence.
To follow Dr. Jess’ ongoing work on all things sex and intimacy, visit @sexwithdrjess, and subscribe below to receive our free monthly digital issue, where conversations like this continue to unfold.
