The Art of Solo Dating: Learning to Redefine and Embrace Connection from an Ethical Non-Monogamous Perspective

I’ll admit that I sat for far too long trying to think of a fitting title for this post.

I played with words and phrases such as independence, adventure, challenge, communication, tips, how to… and then promptly reminded myself that actually, I’m not one to sit here and pretend that I’m an expert in this space. I prefer to explore it all with you.

So I settled for the word art.

I’m a huge fan of art in all of its forms because it’s subjective, it’s liberating, it’s confusing, it’s chaotic, it makes the most sense, it’s messy and ugly and beautiful and it humbles you like no other human experience can.

I even went as far as to acquire a rather passé vine tattoo in my early twenties, that nestled the words ‘Explore the Art of Loving’ in Latin. At the time, I thought I understood the world, and having emerged a few years earlier with two A-levels in Philosophy and Psychology, I was quite chuffed with myself for representing (permanently on my skin, no less) the wise words of Erich Fromm; a German social philosopher and psychoanalyst who wrote The Art of Loving in 1956, and explored love as an artful skill that needs practice, concentration and understanding.

Something that is key to a fulfilling human existence.

Significantly, Fromm also believed that there are many different types of love, such as romantic love, brotherly love, erotic love, the love between parent and child, platonic love, and even the love of somebody’s concept of God. This feels important because certain types of love are often neglected or feared in life, while others are glorified, but I want to explore it all. I’ve always been in search of close connection with other human beings; it’s part of the main reason I became ENM in the first place, and certainly feeds into why I’m moving into solo dating within that dynamic.

Love isn’t to be feared. It’s the whole point.

At this point, you might be thinking…”why are you banging on about art and love when we’re just here to read about how you might have cocked up a date?” And look, you know I’m going to share a date-gone-wrong story with you; I know how to keep a person scanning the page. But… if there’s one thing that I’ve learnt whilst my husband and I are trying to navigate this new dynamic of dating people separately from each other…it’s that it has consistently tested our understanding of love for each other, and has demanded that we develop a certain artful skill set, in order to make it work.

So, settle in for an article in which I:

• define what I mean by ‘solo dating in the ENM lifestyle’;
• offer some suggestions about considerations, and questions to ask yourself and your partner/s before embarking on it;
• explore some challenges I had personally, and some tension points my husband and I experienced between us;
• reflect on how to communicate healthily, when these things happen;
• outline some funny ‘WTF’ moments on my early dating ventures so far;
• pretend to know what I’m doing.

I’m quite enjoying the idea that this reads like an overly-honest Intro Slide of a corporate training day. You know… where Andy ‘Head of People Operations’ Burton has read out every intention of the meeting painfully slowly, and you’ve just realised you sat next to Halitosis Susan from accounts.

But there will be far less BS here, and I’m only going to ‘open the robe’ (ha) on what I feel will be valuable to think about, particularly if you’re in any way curious or actively involved in solo dating within the ENM lifestyle.

What is ‘solo dating’ in the Ethical Non-Monogamous World?

This can be a bit of a minefield.

You’ve probably heard terms such as ‘Single’, ‘Solo Poly’ or ‘Solo Non-Monogamy’. These terms differ from the meaning of ‘solo dating’ that I’m aiming for within this post, but for the sake of comparison and clarity:

Single: A person who isn’t in a romantic relationship with anybody, including long-term dating, engagement, or marriage. As you’ll be aware, it’s a term used more in the monogamous world, since it assumes that the person is either single by choice (and not looking to be romantically involved with another person), or that they are seeking a partner which will likely be of a monogamous nature, one day.

Solo Polyamory: A dynamic in which somebody considers themselves ‘solo’ or ‘single’ and maintains their independent lifestyle, but who may also have (or be open to) multiple intimate relationships with others. Solo polyamorous people are mostly open to concurrent loving relationships, but don’t always live with partners, share finances, or aim to reach traditional relationship milestones. These relationships may remain casual but may also escalate into something more serious or intertwined, over time. Or they may prefer to stay ‘solo’ whilst enjoying different connections.

Solo Non-Monogamy: I haven’t heard this term quite as much, but it could be considered a broader term in which the person practises some type of non-monogamy (could be polyamorous or not) while intentionally remaining without a ‘primary’ partner, ‘nesting’ partner or spouse. They may be open to falling in love (poly leaning) or simply be open to multiple casual partners, but would always aim to communicate their intentions to partners, to set expectations.

Ultimately, it’s best to ask individuals what their unique dynamic is, because each of these terms is on a spectrum; they can be nuanced and they can evolve or change over time.

Now that I’ve described these terms, this post is about a different kind of ‘solo dating’, and despite potential overlaps or similarities, I only aim to talk about my experiences within it. Perhaps some elements of the dynamic I share with my husband might be familiar to you.

Solo Dating: For the purpose of this post, I’m talking about being in a relationship with a primary partner (my husband), who – up until fairly recently- has joined me in most of our intimate experiences with other people. However, we’re now exploring our desire to branch out from group experiences, and make connections with other people, separately from each other. Currently, for my husband, that involves having a female FWB (Friend With ‘Benefits’) and being able to enjoy dates with another woman besides me. For me, solo dating has involved wading through barbaric dating apps and looking for a lovely woman who doesn’t immediately ask to see my tits, or who writes more on her profile bio than ‘Dunno what to put on here’.

It might be prudent to say here that exploring separate or solo dating generally takes us further away from a purely ‘swinger’ space in our dynamic. We’ve personally never labelled ourselves as ‘swingers’ anyway, because it feels more complex than that. We lean towards deeper connections that are sometimes quite emotionally involved rather than focusing on the sexual aspects…but we do acknowledge that we have had ‘swinger-esque’ experiences and have enjoyed group sex on more than a few occasions! I make this distinction not because we hold any judgement towards swinging. It just feels more fitting to place ourselves underneath the broader language of an ‘open marriage’ or ‘ethical/ consensual non-monogamy’.

It took a while to get here though.

The Journey

When we first opened our marriage, we spent two years exclusively playing with another couple, who had been long-term friends. As I’ve explained in previous posts, it was the perfect storm of friendship, sexual tension, open-mindedness, and a well-timed drunken birthday hot tub that set all of this in motion. We didn’t necessarily do all of this by the book, but were lucky enough to enjoy some quality, hot times with these friends. It didn’t come without challenges and by the end of this initial foray into what outwardly presents as ‘swinging’, we all decided to draw a line and end that part of our relationship, in order to maintain our friendship. Which we did.

COVID and Lockdown happened shortly after that, and we took an extended break from the lifestyle owing to the pandemic, and my Mum’s terminal illness. I think this is important to say because for us, we knew immediately that it was time to lean into each other, into family, and spend enough time healing from grief before bringing any other human beings into the fold. Luckily, we didn’t have any established relationships with other people to consider at that time, and so the decision to almost ‘close’ our marriage again for a couple of years was an easy one. In this way, I advocate for regularly checking in with your own mental state and circumstances, in order to make the best decisions for yourself and other people, so that nobody emerges worse-off than before!

Around the Summer of 2022, we both began to get stirrings of curiosity about what a broader ENM dynamic might look like for us, so we booked a social/ sex club event, in which we were thrown into meeting a range of people in this community, and had the chance to explore Le Boudoir in London; our very first lifestyle club. This was an eye-opener, and was equally exhilarating and overwhelming, but it propelled us to book another similar event in Penthouse the following February. In the lead up to this event, something unexpected happened, and we met a couple who slotted themselves beautifully into our lives, like something that was always meant to be there. This taught us that we didn’t want it to be all about sex in this lifestyle. We realised that we had the natural capacity (and openness) to develop feelings and deeper connections, and to enjoy an incredibly close friendship with others. It’s something quite intangible at times, but something we hold very close to our hearts.

Over time, this led to us exploring a few different experiences with this couple and owing to my raging bisexuality, which matches the female half of this couple, we enjoyed the odd hotel night stay together, and our husbands were supportive of that. The intimacy and validation I experienced during this time was so significant, that I began to feel as though I wanted to focus more on building connections with women. Again, this goes deeper than sexual intimacy for me. It’s a celebration of an identity that I suppressed for a very long time, and an expression of myself in all of my wholeness. I wanted more.

And thus began the deeper conversations into whether my husband and I might like to explore solo dating further. The question of whether he would like to date women separately arose, and I was forced to face my own feelings about that prospect. From the very beginning, we had mutually agreed that if I had the opportunity to be with another woman on my own, then he also deserved that freedom. But the reality of a woman sliding into his DM’s was far scarier than I had expected.

Ultimately, we were thrust into putting the work into very honest, open and vulnerable conversations about:

• why we wanted to date separately from each other;
• how we would go about it;
• what we foresaw as the benefits and challenges;
• how we’d cope with these.

These discussions were absolutely essential in addressing some complicated questions, emotions and ‘wonderings’… so I’ll share some tips and consideration points for you to think about below, in case you’d appreciate some guidance here:

Questions to ask yourself when thinking about solo dating:

• Why do I want to date separately from my partner?
• What am I hoping for?
• Am I emotionally ready to date somebody else?
• Do I have the emotional/ mental capacity to fit another person into my life?
• Can I logistically fit another person into my life?
• How might it affect my family?
• How will I look after myself in this process? How will I look after my established partner/s or primary partner? How will I look after the person I am dating?
• Do I want to date casually, e.g. just sex and fun? Or do I want to date in order to find a deeper, emotional connection? Am I open to love?
• How will I communicate this with my partner/s?
• What do I want in a partner when solo dating?
• How will I look for this?
• Am I prepared to accept that my partner may want to date separately as well? What feels ‘fair’?

Questions to ask each other:

*** You’ll notice that these questions aren’t as direct as the questions above. This is because I’ve framed them in a way that a therapist might- in a curious way. This can soften a conversation when we might be feeling heightened or emotional. e.g. Instead of confronting our partner with an abrupt ‘why’, it’s often more helpful to say ‘I’m wondering…’ instead. Hopefully this helps you both to have a calm, supportive discussion, even if you’re feeling vulnerable. ***

• I’m wondering what you’re hoping to experience with solo dating?
• Can you help me to understand how I fit into this process? How our potential partners might fit in?
• I’m curious about what feelings are coming up for you when we talk about this?
• Is there a way for you to reassure me about how I’m feeling here?
• I’m excited about… how do you feel about that?
• I’m worried about… is that something you can relate to? How do you think we could navigate it together if that happens?
• What boundaries should we put in place when solo dating?
• What would help you to feel connected to me when we’re together? What can I do to help facilitate that?
• How will we communicate our needs and feelings to each other?
• What boundaries should we put in place? Are these boundaries final, or is there room for adjustment down the line? Any ‘non-negotiables’?
• How should we address any problems that might arise? Is there a way to remind each other that we are a team when things get tough? What do you need when you’re upset in the moment…. and afterwards?
• How much are you comfortable hearing about, when we talk about our dates?

These are good starting points… but there’ll no-doubt be other things you want to ask, too.

Some useful consideration points before (and during) solo dating:

• How will you manage balance, e.g. if one of you has regular dates (or a regular solo partner) and the other is struggling temporarily to find somebody? If one of you is feeling insecure and the other is enjoying a confidence boost? If one of you has more time to spare than the other?
• How will you navigate the possibility that one day, one of you wants to stop solo dating, and the other doesn’t?
• Have you considered the possibility that one of you might develop deeper romantic/ loving feelings towards your solo dating partner? Is that okay? If not, how will you guard against that? Have you asked yourself why that isn’t okay?
• How might this dynamic impact your life? Will you keep your dating discrete? Would you like to be open about it? Can you balance the needs of the person/ people you date, with the wider needs of your family/ friends/ job…. your own mental health and capacity?

And this one is really important:

• Consider your own ‘stuff’ in all of this.

Are you in a mentally healthy place for solo dating… or ENM in general? Do you have unresolved baggage that you need to resolve first? How will you work through this? Do you even want to?

Before involving anybody else in your life, I’d urge you to explore where some of your ‘stuff’ has come from; explore how that fits into the present, e.g. see if you can separate past traumas or painful experiences from the reality of the current situation (Hint: therapy). Because it’s one thing to be suffering within yourself to some degree if you haven’t yet resolved some things in your life…but it’s an entirely new concern to be dragging somebody else (often inadvertently) into this, when naturally, they will already have their own past and present ready to offer you, all wrapped up with a relational bow.

You don’t have to be perfect. But you do need to be present.

In all manners of the word.

Challenges and Tension Points

I could list a thousand potential challenges within ENM in general, but for now I’ll just talk about a couple of tension points that came up for my husband and I when first dipping our toes into solo dating, and how we navigated them (which continues to be an ongoing process).

The first one of them was back when I’d first begun to happily swipe left and right on a few different dating apps designed for sapphic, or poly/ ENM connections. My husband was quite relaxed about what might come of this for me, whilst remaining fairly satisfied in just continuing to enjoy our established relationships with other couples. He hadn’t yet thought about dating another woman on his own, despite our agreement that this would be okay, if an opportunity arose. In all honesty, this was a very comfortable space for me. I was out there enjoying potential bisexual experiences with other women, and I didn’t have to process any emotions about my husband having his own experiences, because he wasn’t all that bothered.

I had my cake and I was bloody well enjoying eating it too!

However, one evening, we were floating around the hot tub in our garden and a ping went off on my husband’s phone. He glanced down at it and an old, familiar name popped up: T. We’d met T a few times at social events in the past and there’d been a strong attraction between them both. T was interested in getting together and it seemed to be the ideal opportunity for my husband to explore this on his own. On the surface, it felt quite serendipitous, and I watched the smile spread across his lips.

The love of my life was smiling down at the words of another woman. Without me being involved. And unexpectedly, a storm started to brew low down in my stomach. My heart was aching in a way that almost didn’t register. A faint stirring of fear and projections, and a strange longing for a time when we had held hands and made vows on a Cornish beach all those years ago. A more vulnerable and protective part of me was voicing a few concerns like:

What if he doesn’t come home again?

What if the novelty and excitement of being with a new woman blots out years of our history; the laughter, pain, sorrow and joy?

What if he moves further and further away from being … mine?

Over time, when I was able to talk about this with my husband, and with friends I trusted etc, I was able to give myself the grace to understand that these questions were valid. They were coming from the part of myself that wants me to be okay; for us to be safe; to be secure. Most of us grow up with fairly traditional monogamous ideals and I didn’t know how to manage this new thing in our lives.

For a while, I was convinced that my husband would have a taste of this new freedom, and be so intoxicated with the fun of it, that he’d run away from our family and set up a whole new life. I was suspicious that this is what T would want, too. I told myself an intricate story of how in years to come, I’d end up dropping my son off to him and his new woman at the weekend, and I’d be playing sad Patrick Watson songs on the car ride home, and psyching myself up for the rest of my family and friends to tell me “I told you so” when I arrived back at an empty house. I’d end up bitter and alone, take up crochet to kill the hours that ticked by, and realise at 9pm that my underwear had been on inside out all day, and that I’d forgotten to eat lunch or dinner.

To my credit, my therapist says that I’m an excellent storyteller, and he has belly laughed at my ridiculous narratives at time. Which feels pretty great when you’re in the thick of irrational thoughts.

But this also gave me the kick up the butt I needed, to be able to move through them, and see my reality for what it was:

My husband and I had trust. He loved me and I loved him. We had a family built on hopes and dreams that were still very much playing out as we’d hoped. We communicate. We respect each other. This could be fun, liberating and serve us both. We’re strong enough to navigate the challenges and celebrate the joys with, and for each other.

My counsellor also helpfully brought into my awareness the idea of transference, when I was outlining my irrational fears that another woman might want to ‘steal’ my husband away eventually.

Transference is a psychological phenomenon that occurs when someone redirects their feelings, attitudes, or desires about one person onto another.

During my therapy session, I was able to look back into my formative years of early relationships and dating, and recognise that I’d been deeply and repeatedly hurt by one ‘friend’ who convinced my boyfriends to break up with me, so that she could pretend to want them for herself. As an adult remembering this, it feels absolutely trivial and I was quick to dismiss it… but the moment I recognised that the teen version of myself was transferring these feelings directly onto T, I was able to see T for who she actually was: somebody funny, kind, generous, decent… not a carbon copy of a shitty teenage girl who’d once played with my feelings for fun.

So if you’re struggling with painful or uncomfortable emotions when thinking about having separate sexual or romantic experiences from your partner/s, I urge you to do the following:

• Identify the uncomfortable emotion: Where do you feel it in your body? Can you label it? (sometimes we think we’re feeling anger, for example, but that’s a secondary emotion that often disguises fear or sadness).
• What might be causing this feeling? Is it the reality of the current situation, or a ghost from the past?
• Talk about it honestly. Stop hiding your emotions and expecting your partner to be a mind-reader. That’s not fair.
• Put some boundaries in place and stick to them. Communicate at every twist and turn.
• Accept that solo dating (or any new dynamic) might not be for you, whether that’s just for now, or for always. And that’s okay.

Since my husband and I have worked through these things, I’ve now been able to celebrate my husband’s fun dates with this woman much more easily, and have reached a certain level of compersion for his experiences there.

I even ate the chocolate brownies T sent home, which were annoyingly delicious.

And best of all, that security has enabled me to enjoy some funny and exciting experiences in my own dating life since…

So I’ll conclude this post with two short dating stories and a final word. Then perhaps you can decide whether you feel like this solo dating lark is worth it.

A Date with the Police Detective

I’d matched with this woman on a dating site called Feeld.

She was a petite, brunette, detective in the Met, and looked very different in each of her profile photographs. In one picture, she was on a sunny beach in a demure Summer dress, holding some kind of cocktail. In another, she was wearing a subtle leather collar that I suspected reflected a kink of hers, and a domme-like frown.

One part of her bio said “NO I DON’T WANT TO SLEEP WITH YOUR BOYFRIEND”, which I had assumed would probably be the case anyway, since she was a lesbian. Plus I wouldn’t usually open with ‘my husband wants to fuck you’ so I was okay with this. Not to be deterred by the mild aggression of this statement, I sent a nice opening message and we began a conversation. Within a couple of weeks, there had been minimal red flags, other than the fact that she once left me a voicenote while eating lunch, and I could hear her sandwich sloshing around her mouth. So we set a low-key date to meet at a local Mexican restaurant.

When I saw her walking towards me on the night, I noted in my mind that she was very physically attractive, and seemed quite relaxed, which put me at ease. Although I distinctly remember thinking about that opening scene of The Bill as she walked with her long, black trench coat flapping, which meant I had to suppress an almost insane bout of chuckling. Anyway, we ordered a couple of margaritas and some food, and settled into what I thought would be a chilled evening of good conversation, and hopefully some flirting that I didn’t need to second-guess.

However, what ensued was approximately two hours of her angrily telling me about all of her ex-wife’s transgressions, and violently tapping out replies to this ex, in what seemed to be a confusing argument regarding who would attend their daughter’s school meeting the next morning. Unprompted, she showed me these walls of text as I silently eyed her suspiciously from the rim of my salted glass. She went on to say a variety of offensive things about her work colleagues, expressed some problematic views about the trans community, and told me that her friends have always said she has ‘zero emotional intelligence’.

This was evident when she tried to blame her lack of emotional awareness on being an Aquarius.

My silence, coupled with the occasional empathetic nod or confused head-tilt, obviously didn’t compute in her mind, since she continued on in a tirade of huffs and sighs, while shovelling a salad in large forkfuls. Throughout, I had already gently challenged some of her view points, and decided we were absolutely not on the same wave-length, but I was distracted enough by an unusual habit she had of winking one eye every time she chewed, that I hadn’t noticed time flying by.

At the end of the night, we went our separate ways, and she text me saying I’d been super easy to talk to, but she hadn’t felt any chemistry, which was an absolute plot twist, as you can imagine.

I promptly blocked her number.

A Date with Portugal

This is a nice story so you can relax back in your chair.

After a few weeks’ break on the apps, I decided to venture out into the murky world of Feeld again, and after some time, I matched with a beautiful Portuguese woman.

She was a vibrant and interesting extrovert, who had a love of cats, sunshine, the outdoors, baking, reading and a healthy obsession with pineapples. She came with a self-professed cute accent, and seemed to be a pretty optimistic ray of light, despite struggling with the greyness of a British Autumn… and declaring (quite rightly) that most English people look depressed. I explained that this wasn’t depression; it’s simply a hardened shell of sarcasm and resignation that sets in when you’ve dealt with 90% cloud cover and too much time spent queuing.

We ended up spending our first date together eating noodles in an Asian/ Japanese restaurant and I convinced her to play indoor Crazy Golf with me for an hour afterwards. This gave me the opportunity to make fun of her quick-temper when she’d hit the ball far too hard again, and despite the fact that I was in my own head about whether we were flirting or just having fun (or both), she put her hand around my waist towards the end and I could feel a little spark. A tentative one.

As we walked out, she made a cloaked comment about a ‘next time’ and I told myself I had to pull it together in asking to kiss her goodnight, because I was becoming more sure I wouldn’t be rejected. She spoke animatedly about things as we arrived at my car and I noticed she didn’t hurry away… so during a natural pause in the conversation, I took a deep breath and asked if I could kiss her. She said yes and I summoned all the gentle dominance I could, pulled her in to me as I leaned against the driver door, and cupped her face while my lips touched hers. My fingers were woven in her long hair as the kiss grew a little deeper, and when we came apart, she looked at me and told me I’m absolutely not allowed to ghost her after a kiss like that.

And despite it being very, very early days, I’ve had the pleasure of talking to her and enjoyed another date since. Long may the fun continue!

Redefining and Embracing Connection

It’s an uncomfortable thought, but I try to remind myself that we can’t own each other in this life, and that guarantees are just an illusion. As human beings, we struggle so much to grasp onto some semblance of control when in actuality, many things in this world are frustratingly uncontrollable. We spend hours going through every worst-case scenario so that we can feel more prepared, if it happens. But what usually happens is something that’s positive/ isn’t too bad/ something we couldn’t foresee anyway… and yet we’ve still wasted hours, days, weeks, months, years preparing for what wasn’t meant for us in the first place.

Psychoanalyst Donald Winnicott famously said:

“Tell me what you fear and I will tell you what has happened to you.“

When we’re feeling insecure, scared, abandoned, rejected, etc, this is often a projection of the past onto our present. Yes, sometimes the present is genuinely terrifying in some ways, and life (with all of its love, loss and memories) has a funny way of feeling like grains of sand slipping through our fingers. But sometimes, it’s time to introduce yourself to the present as it actually is: something new, something fresh, something that’s full of growth and opportunity. Fear should be listened to and held, like you would when comforting a small child… but it shouldn’t cloud your ability to take the next steps, wherever that path leads.

For me personally, the greatest suffering ultimately sets itself into my bones when I’m desperately clinging onto the things that change.

But for me and my husband, that doesn’t mean that we don’t keep coming home to each other.

Sometimes, one of us will be traipsing through the woods and won’t know which way is up. Sometimes, each of us will have found a new venture and feel joy that didn’t necessarily originate in the heart of the other. But through it all, we can only set an intention to continue being that light in the doorway for each other, when one path has taken us temporarily elsewhere.

Because redefining and embracing connection in my mind, is like the twisting roots and vines of a bonsai tree- sometimes smooth; sometimes woven and tangled; sometimes branching out and twisting in a wayward direction; other times pressed together as though nothing will part them. And if you continue to water and nurture it… it’ll thrive, whatever the direction.