64. From Overthinking to Observing: My Year in Reflection

Retrogrades be retrograding and it has made me reflect on this year!  After coming across a journal prompt, I’ve realisedthat things need to change.In this “Dear Diary” style episode, I'm reflecting on a year of connections, unexpected lessons and personal growth, and what these experiences have taught me about myself.From rediscovering my confidence, sensuality and recognising my own patterns around overcompensating, making excuses and catching myself accepting less than what feels right.I talk about why casual doesn't mean disposable, why emotional safety and consistency matter regardless of relationship labels, and why appreciating a connection doesn't mean you have to keep it.And, most importantly, I explore what it means to trust yourself, stop chasing connection and recognise when something is no longer aligned with what you want.And there's something new coming!I'm introducing The Sunday Read – a new weekly Instagram feature where you can send me those confusing dating messages and conversations for my honestperspective. We'll look at the words, the behaviour, the patterns and what might be happening between the lines.Because sometimes the clarity we're looking for isn't in another message from him. It's in learning how to recognise what we've already been shown. Follow ⁠⁠⁠⁠⁠⁠⁠⁠⁠@vanessamaree_wingwoman⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and every Sunday have to chance to send in something that just doesn't seemright or you want a little read on.Connect with Vanessa Maree and say hello! ⁠⁠⁠⁠⁠⁠⁠⁠⁠@vanessamaree_wingwoman⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow the podcast page ⁠⁠⁠⁠⁠⁠⁠⁠⁠@singleandnotsettling.podcast⁠⁠⁠⁠⁠⁠⁠⁠⁠ Download a copy of the FREE eBook "The Empowered Single Woman" ⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠ to transform your beliefs about dating and find the love you deserve.For interviews and collaborations, email [email protected]

What if choosing yourself doesn't mean you stop loving someone, but that you stop putting your life on hold waiting for them to choose you?In this episode of Single and Not Settling, I'm joined by Elara Song, a medical student and writer working on You Cannot Make Them Stay, a memoir-driven book exploring heartbreak, anxious attachment and learning to build a life that isn't centred around someone else's decision to stay.We explore what happens when you love someone deeply, imagine a future together, and then have to face the reality that love alone doesn't always mean a relationship will continue. How do you move forward when you still have feelings, unanswered questions or a part of you hoping they'll come back? What particularly intrigued me about Elara's journey was her exploration of Stoic philosophy and how she applies its principles to heartbreak and dating. It's not something we often hear discussed in the dating space, yet the distinctionbetween what we can control and what we can’t offers a powerful perspective when we're struggling with rejection, uncertainty or the desire for someone to choose us. In this conversation, we explore:  Choosing yourself: How to stop putting your life on hold while waiting for someone else to decide your future.  The courage to share your heartbreak: Why Elara chose to write about her personal experience and how turning pain into something that may help others can give it a different purpose.  Stoicism and modern dating: How to apply the principles of Stoic philosophy when navigating rejection, uncertainty, attachment and the things we cannot control. Anxious attachment and childhood patterns: How early experiences of needing to give or do things to receive love can influence the way we show up in adult relationships.Building a life of your own: How to stop treating singlehood as a waiting room and start living intentionally, regardless of your relationship status. This episode is a reminder that we cannot make someone stay, return or choose a future with us. But we can decide whether our own future remains suspended while we waitfor their answer. Because being Single and Not Settling isn't about pretending you don't want love. It's about making sure that, while you're hoping to share your life with someone, you don't forget to live it. Connect with Elara Song through her social media and writing platforms hereConnect with Vanessa Maree and say hello! ⁠⁠⁠⁠⁠⁠⁠⁠⁠@vanessamaree_wingwoman⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow the podcast page ⁠⁠⁠⁠⁠⁠⁠⁠⁠@singleandnotsettling.podcast⁠⁠⁠⁠⁠⁠⁠⁠⁠ Download a copy of the FREE eBook "The Empowered Single Woman" ⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠ to transform your beliefs about dating and find the love you deserve.For interviews and collaborations, email [email protected] 🎧 Listen now, and if this conversation resonates with you,share it with a friend who might need the reminder that her life is still hers to live.

In this episode of Single and Not Settling, I'm sharing a recent speed dating experience that had me calling a man arrogant, and reflecting on something much bigger than one uncomfortable conversation.Because while we're out there trying to find connection, chemistry and companionship, women are also navigating questions about their safety that can influence how theyapproach dating.Think about it. Meeting in public, sharing your location with a friend, watching your drink, arranging your own transport and having an exit plan. We're encouraged to take precautions before we've even established whether we like someone.And yet, we can do everything we're told to do and still not have control over another person's behaviour.So why does so much of the responsibility for staying safe fall on women?In this episode, I'm talking about:- The risks women navigate when dating and why a first date can involve more than simply deciding whether there's chemistry.- Women's safety and personal responsibility: why taking precautions matters, but the responsibility for harmful behaviour belongs to the person who chooses it.- The double standards women face when speaking up, setting boundaries or refusing to tolerate disrespectful behaviour.- “It's not all men” — and why acknowledging that doesn't mean we should avoid conversations about violence against women.- What men can do differently to challenge entitlement, respect boundaries and contribute to a safer dating culture.- Wanting love without sacrificing your peace: the reality of being happily single, independent and still questioning whether dating is worth the emotional energy and risks.Women aren't asking for the impossible. We're asking for respect, accountability and the freedom to date without feeling that we always have to be on guard.So, here's the question: When women go on a date, are we thinking about things that men don't always have to consider?Let's have the conversation. 🎧 Listen now and join me as we unpack dating, women'ssafety, accountability and what it means to be Single and Not SettlingConnect with Vanessa Maree and say hello! ⁠⁠⁠⁠⁠⁠⁠⁠@vanessamaree_wingwoman⁠⁠⁠⁠⁠⁠⁠⁠Follow the podcast page ⁠⁠⁠⁠⁠⁠⁠⁠@singleandnotsettling.podcast⁠⁠⁠⁠⁠⁠⁠⁠ Download a copy of the FREE eBook "The Empowered Single Woman" ⁠⁠⁠⁠here⁠⁠⁠⁠ to transform your beliefs about dating and find the love you deserve.For interviews and collaborations, email [email protected]

Is there a better way to date than swiping, apps, awkward first dates… and speed dating in a pub with alcohol involved?I think there has to be!In this episode of Single and Not Settling, Vanessa Maree is joined by Shani Connard, who is doing exactly that — reimagining the way we meet and connect with other people.Shani creates intentional spaces where people can step awayfrom the curated version of themselves we often bring to dating and actually connect as who they are.Think grounding, intentional connection, thoughtfullycurated prompts and a fun little way to let someone know you’d like to see them again. ❤️It’s not just about meeting more people.  It’s about creating the right environment for people to actually connect.In this episode:• Why we often meet strangers as a curated “representative”of ourselves.• Why meeting people IRL can create a different kind ofchemistry.• Finding connection through things you genuinely love doing.• Shani’s experience with open relating / Ethical Non-monogamous relationships (ENM).• The importance of communication in non-monogamousrelationships.• What jealousy can look like in open relating.• And how Shani is reimagining speed dating.Maybe we don't need more ways to swipe.  Maybe we need more reasons to put our phones down, show up as ourselves and meet people in real life.Shani’s event is coming up in early October 2026 with moreevents planned.  Check out the link to her event page below!Check out Shani Connard's upcoming Authentic Dating events hereConnect with Vanessa Maree and say hello! ⁠⁠⁠⁠⁠⁠⁠@vanessamaree_wingwoman⁠⁠⁠⁠⁠⁠⁠Follow the podcast page ⁠⁠⁠⁠⁠⁠⁠@singleandnotsettling.podcast⁠⁠⁠⁠⁠⁠⁠ Download a copy of the FREE eBook "The Empowered Single Woman" ⁠⁠⁠here⁠⁠⁠ to transform your beliefs about dating and find the love you deserve.For interviews or collaborations, email [email protected]

Have you ever looked at a man and thought, “I KNOW he’s not giving me what I need… but I can’t keep away?”In this episode, Vanessa Maree is joined by clinical hypnotherapist Adrianna Carlesimo to explore the subconscious patterns that can influence who we’re attracted to, what we tolerate and why hot and cold behaviour can sometimes feel so compelling.Together, they unpack self-worth, worthiness wounds, emotional unavailability, breadcrumbs and the difference between knowing what we want consciously and what our subconscious may still be programmed to seek.In this episode, we talk about: Why we can be attracted to someone even when we know they're giving us the bare minimum.Why inconsistency and hot and cold behaviour can feel more exciting than consistency.The difference between conscious desiresand subconscious programming.How worthiness wounds can show up in ourdating lives.The relationship between self-worth and what we’re willing to accept.Whether changing our self-worth can change who we're drawn to.... And a little end of recording synchronicity involving two very similar nail polishes!The takeaway in this episode is sometimes the question isn't just “Why do I keep attracting these men?, its “What is the program running in the background and how can I break it so I can be drawn and attracted to a healthy relationship?”Understanding the subconscious patterns behind our attraction doesn't mean taking responsibility for someone else's behaviour. It means becoming curious about our own patterns, strengthening our self-worth and learning to recognise when something familiar isn't necessarily something healthy.Because Single & Not Settling isn't just about having higher standards.It's about becoming the woman who no longer has to convince herself that the bare minimum is enough.To connect or work with visit Adrianna Carlesimo, visit her website Connect with Vanessa Maree and say hello! ⁠⁠⁠⁠⁠⁠⁠@vanessamaree_wingwoman⁠⁠⁠⁠⁠⁠⁠Follow the podcast page ⁠⁠⁠⁠⁠⁠⁠@singleandnotsettling.podcast⁠⁠⁠⁠⁠⁠⁠ Download a copy of the FREE eBook "The Empowered Single Woman" ⁠⁠⁠here⁠⁠⁠ to transform your beliefs about dating and find the love you deserve.For collaborations, email [email protected]

In this episode, Vanessa Maree shares a little update from her matchmaking journey including what happened when she finally agreed to meet the man she was introduced tothrough Love With Me.After stepping away from the dating apps, Vanessa is exploring different ways to meet people and what it feels like to put yourself out there in a different way. And of course, because this is Vanessa’s dating life… there was an urgent bathroom situation before AND during the date. In this episode:Vanessa’s latest update from her matchmaking journeyWhy she decided to give matchmaking a chance after deleting the dating appsSaying “yes” to meeting someone who wasn’t necessarily her usual “type”What it’s like meeting someone in person rather than spending weeks messaging on an appThe benefits of having a two-hour timeframe for a first dateThe very real pre-date bathroom emergency 😂Why matchmaking, speed dating and singles events can be great alternatives to dating appsBeing open to meeting people in unexpected waysHow our idea of our “type” can change as we grow and healYou don’t have to keep dating the same way just because that’s how you’ve always done it.If the apps aren't working for you, there are other ways to meet people. Be curious, try something different and, sometimes, just say yes. You never know where that one yes might lead.If you enjoy the podcast, follow, rate or review it on Spotify or Apple Podcasts. Your support helps more single women find the show.Get in touch with Megan Gourlay from Love with Me here: ⁠www.lovewithme.com.au⁠Connect with Vanessa Maree and say hello! ⁠⁠⁠⁠⁠⁠@vanessamaree_wingwoman⁠⁠⁠⁠⁠⁠Follow the podcast page ⁠⁠⁠⁠⁠⁠@singleandnotsettling.podcast⁠⁠⁠⁠⁠⁠ Download a copy of the FREE eBook "The Empowered Single Woman" ⁠⁠here⁠⁠ to transform your beliefs about dating and find the love you deserve.

You thought it would have happened by now. You thought you'd meet someone. Fall in love. Get married. Maybe build the life you'd imagined together.Because that's what seemed to happen for everyone else.And now you're in your 40s, still single, looking around wondering...“Why hasn't it happened for me?”But what if your life isn't supposed to wait for that? That's the conversation I had with my latest guest on Single and Not Settling, Ingrid Bayer, author of Not Done Yet – A Journey Back to You. And while Ingrid's story isn't specifically about being single, her message hit me deeply: You are allowed to reinvent yourself when love hasn't happened yet.In our conversation, we talk about:Why you don't need to wait for a relationship to start creating the life you want.Giving yourself permission to reinvent yourself at ANY stage of life.How to recognise when your life no longer feels like your own.What to do when you're single and don't know what your next chapter looks like.Practical ways to use your time to discover who you are again.What “not settling” looks like when it comes to the life you're creating. And you don't have to spend the next five years wondering what is wrong with you because you're not where you thought you'd be. Instead, you can ask: Who am I now? What do I want my life to look like? What have I been putting off? Because maybe this isn't about accepting that you'll be single forever. Maybe it's about refusing to put your life on hold while you wait to find out. If you're single and wondering what this next chapter could look like, this conversation with Ingrid might be the permission slip you didn't know you needed.To connect with Ingrid Bayer, visit her website hereConnect with Vanessa Maree and share your favourite takeaway from this episode ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@vanessamaree_wingwoman⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow the podcast page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@singleandnotsettling.podcast⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ For collaborations or interviews email [email protected] - I love would love to hear from you!Download a copy of the FREE eBook "The Empowered Single Woman" ⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠ to transform your beliefs about dating and find the love you deserve.

Are your standards really too much... or have you simply been asking the wrong people to meet them?This week's episode was recorded in my holiday cabin while I was taking a break, wearing no make up and simply being me.  I'm sharing a recent dating experience that reminded me of something I've been learning over and over again, my standards aren't too much.After my experience with "Mr Singapore", I knew I wanted to do things differently. Rather than waiting to see how someone showed up, I communicated from the very beginning what was important to me: consistency, communication and consideration.And something unexpected happened. He simply said, "I can meet that." In that moment, I realised I wasn't asking for too much. I'd simply been asking the wrong people.This episode is also a reminder that dating isn't just about finding the right person, it's an opportunity to practice using your voice, honouring your standards and trusting yourself when something doesn't feel aligned.We also explore a simple question I've started asking when dating. Instead of asking, "What are you looking for?", try asking: "What are you ready for?"Because being ready for a relationship is very different to simply wanting one. Your standards aren't there to push the wrong people away—they're there to allow the right people to come closer.Remember, we’re not waiting to be chosen. We’re choosing ourselves. Connect with Vanessa Maree and share your favourite takeaway from this episode ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@vanessamaree_wingwoman⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow the podcast page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@singleandnotsettling.podcast⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ For collaborations or interviews email [email protected] - I love would love to hear from you!Download a copy of the FREE eBook "The Empowered Single Woman" ⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠ to transform your beliefs about dating and find the love you deserve.

What if the biggest thing holding you back in dating isn't finding the right person... but trusting yourself?After sharing the story of "Mr Singapore" in last week's episode, I realised there was a deeper conversation to have. One that goes beyond dating and into the relationship we have with ourselves.Self-trust isn't something we're born with. It's something we build.But what happens when life experiences, criticism, or constantly second guessing yourself have made it difficult to believe in your own decisions?In this episode, I'm exploring why so many women struggle to trust themselves, how that shows up in dating and everyday life, and practical ways to start rebuilding that trust—one small promise at a time.We'll also dive into some reflective questions to help you uncover where your self doubt may have begun, so you can move forward with greater confidence and clarity.In this episode, we discuss:Why self-trust is one of the most valuable skills you can develop.How childhood experiences and past relationships can shape your decision-making.The difference between intuition and overthinking.Practical ways to build self-trust through everyday actions.Why keeping promises to yourself creates confidence and momentum.How trusting yourself can change the way you date, set boundaries and make decisions.Because the goal isn't to become someone who never questions herself.It's to become a woman who trusts herself enough to move forward anyway.If this episode resonates with you, I'd love for you to leave a review, share it with a friend, or tag me on Instagram. Your support helps more women discover the podcast and reminds them that being single isn't a waiting room—it's an opportunity to build a life you truly love!Connect with Vanessa Maree and share your favourite takeaway from this episode ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@vanessamaree_wingwoman⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow the podcast page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@singleandnotsettling.podcast⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ For collaborations or interviews email [email protected] - I love would love to hear from you!Download a copy of the FREE eBook "The Empowered Single Woman" ⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠ to transform your beliefs about dating and find the love you deserve.

One thing I found myself questioning is the advice we often hear around casual dating. The idea that because it's casual, you shouldn't expect much.  I am challenging that in this episode.In this episode, I take you behind the scenes of a recent interaction I had with “Mr Singapore” (if you follow me on social media you will know), including the actual text messages exchanged between us, what I noticed, how I felt, and the final message I sent when I realised the connection was no longer aligned with the standards I have for myself.This episode isn't about him. It's about self-respect. It's about standards. And it's about questioning the dating advice so many women have been taught to accept.In this episode, I explore what it looks like to honour yourself, communicate your needs, and choose your standards—even when there is chemistry, attraction, and potential.Inside this episode:✨The full story of "Mr Singapore".✨The final message I sent expressing how I felt and what I require in my relationships.✨Why consistency and consideration have become non-negotiable standards for me.✨ The difference between being understanding and abandoning yourself.✨ Challenging the narrative that women should expect less simply because a connection is "casual".✨ Why self-respect matters regardless of the label on the relationship.This episode is for any woman who has ever questioned whether her standards are too high, worried she was asking for too much, or tried to convince herself that breadcrumbs were enough because the connection wasn't "serious."And the right connection will never require you to abandon your needs to keep it.Connect with Vanessa Maree and share your favourite takeaway from this episode ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@vanessamaree_wingwoman⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow the podcast page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@singleandnotsettling.podcast⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ For collaborations or interviews email [email protected] - I love would love to hear from you!Download a copy of the FREE eBook "The Empowered Single Woman" ⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠ to transform your beliefs about dating and find the love you deserve.