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“Do I want to date again? Is it worth the effort at 68 years old?” I answer this dating dilemma here and on the podcast. — I’m so excited to introduce something new here at Last First Date: Dating Dilemmas . Readers and listeners submit their real dating questions and dilemmas, and I answer a selection of them right here on the blog, and on Last First Date Radio as video and audio episodes. If you have a dating dilemma you’d love answered, submit yours here: https://tinyurl.com/datingdilemma Our first Dating Dilemma comes from a woman who sent in this question: “How do I determine if I even want to date or have another relationship? 68 years old, two marriages (24 and 10 years). A few long term relationships. Last one ended over a year ago. I am financially secure and have some good friends. Like having my own space. I do miss intimacy but that is not guaranteed with men in my age range. Every time I start to prepare to go on the...

How is the alpha male mindset sabotaging dating and relationships? Listen to Dave Rossi, a recovering alpha male who remarried after changing how he approached dating. — Dave Rossi is the author of Alphas Die Early: For the Man on a Mission—And the Women Who Love Him and the #1 bestselling book The Imperative Habit: 7 Non-Spiritual Practices Towards Spiritual Behavior – For Happiness, Health, Love, and Success. Dave’s work challenges outdated models of masculinity and success, guiding men to move beyond performance and into authenticity, emotional strength, and purpose. His perspective helps individuals build deeper, more meaningful relationships by aligning how they live with who they truly are. In this episode: Why the alpha male mindset is sabotaging dating and relationships How to date with more discernment The importance of defining your values and boundaries when dating Why difficult conversations are crucial to intimate relationships ...

There are so many reasons you should be having difficult conversations in dating and relationships. Here are the top five. — Most of the conversations we talk about in the world of dating and relationships focus on what can go wrong when things get hard. And there is good reason for that. Conflict handled poorly does real damage. But I want to focus on what happens when a hard conversation goes well, because in my experience, that outcome is far more powerful. And the benefits of having these conversations, the real ones that matter to you, are worth understanding clearly before you talk yourself out of having them. Here are five things that can genuinely shift when you learn to speak up. 1. You Discover Whether the Relationship Works for You One of the most important things a difficult conversation does is give you real information about the person you’re with. How does he respond when you tell him something he might not want to hear? ...

How can we overcome limerence and find true love? Amanda McCracken wrote a fabulous book on this topic. Tune in to the pod to learn more. — Do you want to overcome limerence and finally have a healthy relationship? My podcast guest, Amanda McCracken, wrote the book on how to stop infatuation to find authentic love. She’s a journalist passionate about experiences that highlight the intersection of wellness, travel, and relationships. Her work has appeared in The New York Times, Washington Post, Guardian, Vogue, and many others. She is considered a “limerence expert” and intimacy advocate. Her 2023 TED Talk, “How Longing Keeps Us From Healthy Relationships,” and her podcast, The Longing Lab, highlight how longing can become self sabotaging and shares how to change our patterns of longing. McCracken is also a part-time university instructor, massage therapist, triathlon coach, and competitive athlete.  In this episode: The key characteristics of limerence ...

If you’re afraid of speaking up when you have something important to say, this is for you. Have difficult conversations with more ease. — Ask someone why they haven’t had a particular conversation yet and they will almost always have a perfectly logical explanation. The timing wasn’t right. He seemed tired. She was in a good mood and I didn’t want to ruin it. I needed more time to sort out my own feelings first. I wanted to wait until things were more serious. All of these feel reasonable in the moment. And that is exactly what makes avoidance so hard to recognize in ourselves. Our brains are good at generating excuses for staying quiet. Understanding why we avoid difficult conversations is the first step toward changing the pattern. Below are five of the most common reasons, and what each one is really telling us. 1. The Fear of Rejection Feels Like Protection For many of us, the deepest fear underneath a difficult co...

Nice guy syndrome: why trying to please everyone is making men weaker. Tune into the pod to learn more from the Therapy Brothers! — Why do so many men think being the “nice guy” is a good thing? Meet the Therapy Brothers, licensed clinicians and brothers Brannon and Tyler Patrick, redefining mental health and modern masculinity. Through their popular podcast and clinical work, they break down complex psychological barriers into actionable advice on trust, betrayal, addiction, and emotional resilience. With humor, heart, and refreshing honesty, they tackle relationship dynamics, trauma healing, and the ‘why’ behind our habits. Get ready to dive deep. In this episode: How “Mr. Nice Guy” isn’t actually nice Why men become the “nice guy” How the nice guys can break the pattern of people-pleasing The connection between nice guy syndrome and addiction EP 712: The Therapy Brothers – The Shocking Psychology of Nice Guy Syndrome ...