Hello, my gorgeous friends, and welcome to the very first episode of The Dating Lounge Podcast. I’m so happy you’re here.

Let me introduce myself properly. My name’s Ayesha Hilton, and I wear quite a few hats. I’m a creator, a coach, and a mentor. I’m also a Human Design coach. I love community, and I’m passionate about creating resources and practical solutions to help people in real, everyday ways. I live in a large country town in Victoria, Australia, and I’m the mum of two beautiful kids — a 19-year-old and a 13-year-old with two different dads.

I’ve been married once and divorced once, and I have an amicable relationship with my ex-husband as we co-parent our younger child. I’m also a lifelong learner. I always seem to be diving into a new course or training, and then I love sharing what I learn with my community, if it feels relevant and useful.

Now, here’s something you should know about me. I didn’t grow up fantasising about a wedding. My mum had four kids under four, to three different dads. She ended up marrying the father of her third and fourth children just to make my grandmother happy, because she was religious. So I wasn’t fed that white-wedding fairytale.

Even when I got married myself, of course I intended for it to last — but I never had that “forever and ever” fantasy. I know many women did, and I know a lot of you listening grew up with that dream, but things are changing. If you look at younger people now, they’re not nearly as attached to the wedding fantasy as previous generations were.

Back in 2008, I met my first husband through RSVP — remember that one? Pre-dating apps, in the early online dating days. Later, I met my most recent partner on Plenty of Fish, and we had a wonderful eight-year relationship. And now, here I am — single again and back out there dating, looking for my next person.

Through all of these experiences — the fun, the funny, the painful, and the deeply human — I realised how little support there is for women in our 40s, 50s, and beyond who are dating. That’s why I created The Dating Lounge.

The Dating Lounge isn’t just a podcast. It’s a community. It’s a place for women in mid-life like us to come together, to share our stories, to laugh, to support one another, and to remind ourselves that dating at this stage of life can actually be fun, sensual, and empowering. Inside the community, I host a private podcast, a safe space to connect, and meaningful conversations that remind you that you are not alone.

Because here’s what I believe with my whole heart: women in their 40s, 50s, and beyond are bloody amazing. While some men our age seem like they’ve hit pause or they’re done, I honestly believe we’re just getting started. We’re taking care of ourselves, we’re learning, creating, thriving, and stepping into our purpose. This is our era.

And yes, dating is part of that, but it’s about so much more. It’s about living fully, embracing our sensuality, and knowing that love is still possible. And honestly, mindset plays such a huge role in this. If you go into dating thinking it’s hopeless, you’ll only see the evidence for that. But if you go in believing, as I do, that there are good men out there — kind, loving, available men — then you’ll see the evidence for that instead. My confirmation bias is that I meet good men. And that’s what I want for you too.

So whether you’re just dipping your toes back into dating, whether you’re still healing after heartbreak, or whether you’re already out there swiping and going on dates right now — you are in the right place.

This podcast is going to feel like a conversation with a trusted friend. Together, we’ll share stories, explore the challenges of dating in midlife, and most importantly, we’ll keep it light, hopeful, and joyful.

And if you’d love to go deeper, I’d love for you to join our community. You can find The Dating Lounge

Dating after 40 can be exciting, but let’s be honest, it can also be exhausting. There are good men out there. I’ve met plenty of them. But not every man you meet is ready for real partnership. Some are simply looking for convenience.

And lovely, you are nobody’s convenience.

I have fallen into dating a couple of guys that were just stringing me along. They wouldn't commit to a date or plan in advance. They would text me sporadically. I would try to break things off with them and then they would suddenly want to spend time with me.

Here's what have learnt about dating a guy who might be enjoying your company but not truly investing in you.

If you hear from him when he’s bored, lonely, or has a gap in his schedule, but he doesn’t check in just to see how you are, that’s not care. That’s convenience.

He never makes the effort to suggest dates, ideas, or move things forward. If you stopped reaching out, chances are the connection would fizzle. That isn’t partnership. That’s you carrying the energy.

One week he’s all in, the next he disappears. True interest is steady. Inconsistency often means he’s keeping his options open.

A man who is genuinely interested wants to know your world. Does he ask about your dreams, your family, your past? Or does he keep things surface-level? If he’s not leaning in to know you, he’s not investing in you.

If you’ve been seeing each other for a while and he sidesteps every conversation about “where this is going,” it’s because he doesn’t want it to go anywhere. He’s happy keeping it comfortable for him.

If your needs, feelings, or boundaries are brushed aside or met with irritation, that’s a clear sign he isn’t seeing you as an equal partner. That’s convenience, not commitment.

Deep down, you know. If you feel like you’re waiting for scraps of attention or if your intuition whispers, “you deserve more,” listen. Your body never lies.

A man who’s truly interested will make it known. He will show up consistently, ask about your life, respect your boundaries, and make space for you in his world.

Anything less is not the love you are calling in.

So the next time you feel unsure, ask yourself: Am I being cherished, or am I just being convenient?

You are not here for crumbs. You are here for the whole damn cake.

Want more juicy content?

Join the community at mydatinglounge.com — it will redirect you straight to where we gather. Inside, you’ll find connection, conversation, and encouragement from women just like you.

Love

Ayesha Hilton

One of the most helpful things I’ve learned about love and dating is the concept of attachment styles. This is simply the way we connect, bond, and respond in relationships. It comes from our early life experiences, but it shows up again and again in our romantic lives, even when we’re dating after 40, 50, or 60.

Understanding your own attachment style (and spotting it in others) can save you so much time and heartache. To make it easier, let’s think of attachment styles as different kinds of dance partners. Dating really is like a dance, and each style has its own rhythm.

Secure partners are like steady dancers. They listen to the music, keep the rhythm, and hold their partner with care. Dancing with them feels natural and easy, and you don’t have to guess where you’re going next.

In dating, secure people are consistent, reliable, and clear. They make you feel calm, safe, and valued. If you feel like you can just be yourself around them, that’s the magic of secure attachment.

I experienced this in my previous relationship of 8 years. We had a very solid connection. I didn't feel anxious in our connection. This was a healing relationship for us both. We learnt a lot about how to be in a healthy relationship.

Anxious types dance really close, sometimes a little too close. They crave closeness and can worry about being rejected or abandoned. In dating, this may look like overthinking, wanting constant reassurance, or feeling unsettled if replies are slow.

With the right partner, they can relax into the music, but with the wrong one they may feel constantly off balance. If you notice you’re always on edge, your anxious side might be getting triggered.

If I am not feeling secure in my attachment, especially when I am dating someone new, I can get anxious quite quickly. I have sometimes felt anxious about something specific thought, and later realized that it was my intuition communicating with me and I misread it as anxiety. I am learning to discern the difference between anxious attachment, when I am not feeling connected and secure with a man, and when my intuition is telling me something isn't quite right.

Avoidant types are like dancers who keep stepping back. They value independence and can find too much closeness uncomfortable. In dating, they may dodge emotional conversations, keep things casual, or pull away when it feels “too serious.”

Dancing with them can feel like you’re chasing, while they keep slipping further away. They can be kind and caring, but they often need more space than feels comfortable in a partnership.

Being with someone with an avoidant attachment style can really increase my anxiety. I am someone who wants to fix things straight away when there is a problem. This is almost impossible when you're with an avoidant person as they just want to get away from the situation. I am learning that avoidant people need space and I need to be patient and wait for them to come back. I find this incredibly challenging.

This is the trickiest partner on the dance floor. Sometimes they pull you close, sometimes they push you away. It’s a mix of wanting connection and fearing it at the same time.

In dating, this can look like hot and cold behavior that leaves you confused. One moment they’re all in, the next they disappear. Dancing with them can feel like mixed signals set to music.

I have experienced this and it is very confusing. It's a bit of a mind f*ck to be honest. And you can feel a bit crazy with this attachment style.

Attachment styles are not about good or bad. They’re simply patterns. And patterns can change with self-awareness and healing.

The most important thing is to notice how you feel around...

I was on a date, sitting across the table with a drink in hand, telling him about this funny pattern in my life. Everywhere I go, people give me things for free. A cupcake here, a sample there, little gifts that just seem to find me.

I laughed as I said it, then added, almost as an afterthought, that what I don’t like in dating is being breadcrumbed. I’m over it. I don’t want crumbs of attention, I want the whole loaf.

Not two minutes later, as if the universe wanted to prove a point, one of the bar staff walked over, looked me directly in the eye, and asked, “Do you want this loaf of sourdough bread?”

A full, gourmet loaf, not just a slice. I couldn’t have scripted it better if I tried. The kitchen was closing, and they had extras, but to me it felt like a sign. Ask for the loaf, and the loaf will come.

That’s the thing about breadcrumbing in dating. It looks like little texts that don’t lead anywhere, vague promises of plans that never happen, likes on your photos without a real conversation.

It’s attention in tiny bites, just enough to keep you hanging on, but never enough to actually nourish you. And for a while, it can feel flattering or hopeful.

You think, maybe if I stick around, these crumbs will add up to something. But they don’t. They just keep you hungry.

That night reminded me that settling for crumbs only leaves you unsatisfied.

The right person won’t ration out their time and affection like it’s scarce. They’ll show up fully, with effort, with intention, with consistency.

They’ll bring you the whole loaf, warm and hearty, without you having to beg for it.

So now, when I notice someone breadcrumbing me, I don’t take it as a challenge to win them over. I take it as a clear answer. Crumbs aren’t enough. I’ll wait for the loaf.

And if the universe happens to send it straight to my table while I’m telling the story on a date, all the better.

If you’re noticing breadcrumbing in your own dating life, here are a few gentle ways to handle it:

• Notice the pattern and name it for what it is. A crumb is just a crumb, not a promise of more.
• Ask yourself how you feel after each interaction. Do you feel good, valued, connected, or do you feel strung along?
• Communicate clearly if you want more. Sometimes people don’t realise they’re coasting, and it’s fair to say, “I’m looking for more consistency.”
• If nothing changes, step back. Protect your energy and keep space open for someone who’s ready to give more than a crumb.

Because at the end of the day, you don’t need to survive on scraps. You deserve the loaf.

Join the community at mydatinglounge.com — it will redirect you straight to where we gather. Inside, you’ll find connection, conversation, and encouragement from women just like you.

Love

Ayesha

Dating as a Single Parent

When my daughter was just three weeks old, I became a solo mama. I had to leave an abusive relationship, and from that moment, my whole focus was on her. Dating wasn’t even a thought. I was in survival mode, pouring everything I had into keeping her safe and well.

For the first year and a half, it was just us two. My days were full of nappies, sleepless nights, and trying to put one foot in front of the other. But when she was about 18 months old, I felt something shift. I’d survived those raw early months, and a little part of me began to wonder if love might be possible again.

So, I dipped a toe into online dating. Back then, it wasn’t apps on a phone — it was a website called RSVP. And that’s where I met my husband. He came into my life when my daughter was two. He didn’t just love me, he cared for her too, stepping up as a father figure. We got married, had our son, and for a while, we built a family together.

When our marriage ended, I gave myself time. Two years, to be exact. Time to heal. Time to find myself again. Time to just be a mother before I could even think about being someone’s partner.

When I was ready, I tried again — this time on Plenty of Fish. And I had a surprisingly good experience. I met someone I connected with instantly. Emotionally, mentally, physically — it all clicked.

We ended up sharing eight years together. From the start, I knew there was an issue. In fact, after our second date, I told him I didn’t think we should continue because of it. He begged me to give him another chance, promised he’d work on it. And while he never really did, there was so much good in that relationship too.

My daughter became very unwell during those years, and he stood by me through it all. He gave me support I’ll forever be grateful for. Truly, I don’t know how I would have made it through those dark times without him. That relationship wasn’t wasted — it gave me love, companionship, and strength when I needed it most.

But eventually, the cracks that were there from the beginning never healed. My beautiful son and my partner never fully clicked, and the tension between them was hard to live with. As the years went by, I realised I wanted more. He wasn’t a bad man — in fact, he was a good one — but he wasn’t the right one for me and my children.

And most importantly, he wasn’t meeting my needs as a woman. Because dating as a mama isn’t only about our children. It’s about us too. We aren’t just mothers. We are women, sensual and sexual beings who crave intimacy, passion, and connection. That part of us matters just as much as the part that nurtures and protects.

Dating as a mama isn’t the same as dating before kids. There are layers of complexity that only mothers truly understand:

👶 When to introduce your children

This is the question that keeps us up at night. Too soon, and the kids get attached before we’re sure. Too late, and our lives never really blend. I’ve learned it’s about following your instincts — you’ll know when it feels secure enough to bring them together.

👥 Blending relationships

Will your kids and your partner get along? Sometimes it’s beautiful, and sometimes it’s painfully difficult. When it doesn’t work, it can leave you feeling torn in two, like your heart is being pulled in different directions.

💔 Heartbreak for children

It isn’t just us putting our hearts on the line. Our kids can grow to love someone, and when that person is no longer around, they feel the loss too. I once met a man who adored his stepchildren so much that he stayed in their lives even after separating from their mother. That kind of love left a mark on me.

⏳ Finding time for yourself and a partner

When your kids are young, time is scarce. Babysitters,...

Have you ever wondered why some relationships flow effortlessly while others feel like hard work? Human Design offers us a lens to understand not only how we’re wired, but how we connect with others — in love, dating, and beyond.

It’s not about “good” or “bad” matches. It’s about awareness. When you understand your design (and your partner’s or date’s), you stop second-guessing and start relating with compassion and clarity.

If you don’t know your type yet, you can get your free Human Design chart here: 👉 Get Your Chart

I’m a Certified Human Design Coach, and one of the ways I love experimenting with Human Design is through dating.

In my dating life, I’ve managed to get the birth details of many of the men I’ve dated and it’s been fascinating to see how our charts and energy types played out in real life.

As an Express Builder (Manifesting Generator), I’m naturally always on the go. Starting projects, doing things, moving fast. The only time I really stop is when I’ve completely drained my battery. And then I rest before going again.

When I was married to an Advisor (Projector), I expected him to keep up with my pace. I couldn’t understand why he needed so much rest or why he didn’t just take action the way I did. Honestly, it frustrated me.

But once I discovered Human Design, it all clicked. He wasn’t lazy or unmotivated. He was simply designed differently. Advisors/Projectors are here to guide and shine in bursts of wisdom, not to run endlessly like Express Builders/Manifesting Generators.

That realization changed everything. I could finally accept him lying on the couch watching a show while I buzzed around doing things. Instead of judging, I began to appreciate our differences.

I’ve also noticed that I’m most naturally attracted to other Express Builders like myself, we match each other’s fast-moving, multi-passionate energy.

On the other hand, I’ve found that dating Initiators (Manifestors) can be more challenging. Their energy is closed when they’re not actively thinking about me, and I can sense that intuitively. When I’m not feeling secure, this dynamic can trigger my anxious attachment style. When I am grounded and secure, though, I can admire their independence and powerful spark.

Interestingly, in my business, Advisors (Projectors) love working with me as they can lean into my Express Builder energy and hold space and accountability for their projects.

Builders are steady, glowing bonfires. They bring warmth, light, and consistent energy — but they only truly shine when they’re doing what they love. In relationships, their joy is contagious.

Do:

✔️ Ask yes/no questions to help them respond

✔️ Encourage what lights them up

✔️ Let them share their excitement

Don’t:

✘ Push them to initiate or make decisions on demand

✘ Expect enthusiasm if they’re stuck doing what drains them

Express Builders are like fireworks — dazzling, fast-moving, and full of variety. They love to explore, pivot, and try new things. Their energy can light up a relationship, as long as they feel free.

Do:

✔️ Celebrate their flexibility and enthusiasm

✔️ Be open to their many passions

✔️ Allow them to change direction

Don’t:

✘ Box them into one path

✘ Criticize them for moving...

Anxiety and Dating

Let’s be real. Dating is vulnerable. You’re meeting new people, putting yourself out there, and sometimes sitting across from a complete stranger wondering if you’ve got spinach in your teeth or if they’ve got 100 red flags.

It’s normal for anxiety to pop up in the process.

And when you’re dating after 40, 50, or 60, there can be an extra layer of pressure. You’ve lived a life, maybe raised kids, had long-term relationships, or gone through heartbreak. You know what you want (and what you don’t), but that doesn’t mean your nervous system always cooperates.

The truth is, a little bit of anxiety is completely normal in dating. The key is learning how to work with it instead of letting it run the show.

Anxiety shows up for lots of reasons:

• Worrying if you’ll be liked or accepted
• Overthinking texts and messages
• Playing out “what ifs” before the date even happens
• Reliving past disappointments and assuming they’ll happen again

Our brains are wired for survival, not romance. So if you feel that racing heart before a date, that’s just your body trying to protect you. The good news? You can calm your system and still show up as your authentic, magnetic self.

Take a moment to pause and breathe deeply before opening the apps or walking into a date. A few slow breaths tell your body: “I’m safe. I’ve got this.”

You don’t have to reply to messages instantly. You don’t have to say yes to every invitation. Protecting your energy by moving at your pace reduces overwhelm.

Turn getting ready into self-care. Light a candle, play music, wear something that makes you feel radiant. This shifts the focus from “Will he like me?” to “Do I feel good in myself?”

Not every date will lead to love. That doesn’t mean you’ve failed. Each date is practice, information, and sometimes even just a funny story to share with friends.

Write down three things you love about yourself before a date. Keep them in your mind as you walk in. When you’re anchored in your own worth, anxiety loses its grip.

Dating doesn’t require perfection. It requires presence. When you can notice your anxiety without judging it, give yourself compassion, and take small steps to soothe your body, dating becomes less about pressure and more about possibility.

So the next time your heart races before a date, remind yourself: This is just energy. This is my body protecting me. And I get to choose how I dance with it.

Because love isn’t about being fearless. It’s about being real and showing up anyway. 💕

I have found that especially as I am now in peri-menopause, my anxiety has increased and dating exacerbates that. I have had to really lean into nervous system regulation as I can easily become dysregulated in this dating journey.

One day, before a date with a guy I really like, I felt him go cold and withdraw his energy. I couldn't regulate my nervous system and I had to go to a dear friend's house to borrow some regulation!

Here’s to learning more about ourselves and self-regulating. If you’re comfortable sharing, I would love to know more about your experience of anxiety and dating, and if you have any tips to share.

And…here’s my album on Spotify that is great music to pump you up for your date:

Sugar Rush on Spotify

Join the community at mydatinglounge.com — it will...

When you’re dating, it’s so easy to get caught up in the spark. A smile, a flirty message, the thrill of someone new (I am very guilty of this as I fall all in pretty quickly and I am so open hearted).

But underneath the excitement, there are often little signs we brush aside. Red flags rarely arrive as a giant warning sign; they tend to slip in quietly. If you follow the Burned Haystack Method, you become more adept and seeing the red flags.

A red flag is anything that makes you feel uneasy, second-guess yourself, or question your worth. It’s often found in the gap between what someone says and what they actually do. Maybe they tell you they’re keen to see you but never lock in a time. Maybe they pop up with a “hey” after disappearing for a week. These little mismatches matter.

Obviously, the opposite of red flags are green flags — the behaviours that make you feel calm, valued, and steady. It’s just as important to notice these so you’re not only avoiding what drains you but moving toward what sustains you.

Here’s a simple way to check in with yourself when you’re meeting someone new:

❌ Red Flag Checklist

❌ They text but never follow through with plans

❌ Their words and actions don’t match

❌ You feel more anxious than calm around them

❌ They dodge simple questions about their life

❌ Every ex they talk about is “crazy” or the problem

❌ They dismiss your boundaries or make you feel silly for asking

❌ You find yourself waiting or hoping they’ll change

❌ Breadcrumbing: little crumbs of attention but no real effort

❌ Love-bombing followed by withdrawal

❌ Hot-and-cold communication

❌ Emotionally unavailable but giving just enough to keep you hooked

✅ Green Flag Checklist

✅ They follow through and keep their word

✅ Their actions and words line up

✅ You feel calm, confident, and more like yourself around them

✅ They answer your questions directly and openly

✅ They speak respectfully about past partners

✅ They listen to and respect your boundaries

✅ You feel valued without having to prove yourself

✅ They are emotionally available and steady

✅ They make space for you in their life naturally

✅ The effort feels mutual — you don’t have to chase

This kind of list isn’t about being harsh or judgmental. It’s about noticing. If you see a pattern of ❌s stacking up, it might be time to step back. If you see the ✅s shining through, that’s where your energy is best invested.

Join the community at mydatinglounge.com — it will redirect you straight to where we gather. Inside, you’ll find connection, conversation, and encouragement from women just like you.

Love

Ayesha