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...