Why You Keep Dating the Same Type of Person (And How Personal Branding Can Break the Cycle)

You're scrolling through your dating app for the hundredth time this month, swiping past the same types of profiles that somehow keep finding their way into your matches. The entrepreneur who talks a big game but never follows through. The emotionally unavailable charmer who disappears after three dates. The person who seems perfect on paper but leaves you feeling completely disconnected. Sound familiar? If you're nodding your head right now, you're not alone—and more importantly, you're about to discover why this keeps happening.

Lee Rogers, co-host of the popular Love Lately podcast and author of "Out of the Shadows and Into Your Light," brings a unique perspective to the dating conversation that most relationship experts miss entirely. As a personal branding strategist who found love later in life, Lee understands that successful relationships aren't just about finding the right person—they're about becoming the right person. Her approach combines professional branding expertise with real-world dating experience, creating a framework that goes far deeper than typical dating advice.

In her latest solo episode, Lee tackles one of the most uncomfortable truths about modern dating: we consistently attract who we are, not who we want to be with. This isn't about blame or shame—it's about taking control of your dating destiny through intentional personal branding. Lee's methodology challenges singles over 40 to stop hoping for different results while maintaining the same approach and instead examine the energy, values, and daily habits that shape who they attract into their lives.

The Uncomfortable Truth About Attraction Patterns  

Lee doesn't sugarcoat the reality that many daters face: if you've been "kissing a lot of frogs," your personal brand might be sending mixed signals about who you really are. This concept initially sounds harsh, but Lee clarifies that this isn't about self-blame for past relationship failures. Instead, it's about recognizing that we often present one version of ourselves while unconsciously living another, creating a disconnect that attracts the wrong matches.

The pattern becomes clear when you examine your dating history with fresh eyes. Lee explains that many people create detailed checklists for their ideal partner—wanting that "king" or "queen"—while never stopping to ask whether they themselves would appeal to such a person. This mismatch between aspirations and reality creates a cycle where you keep meeting people who don't align with your true values, simply because your authentic self isn't clearly defined or consistently expressed.

Breaking this cycle requires honest self-reflection about the gap between who you think you are and who you actually show up as in the world. Lee emphasizes that this process isn't about changing your core identity, but rather about aligning your daily actions, energy, and presentation with the values you claim to hold. When this alignment happens, you naturally begin attracting people who appreciate and share those genuine characteristics.

The Self-Audit Revolution: Calendar and Bank Account Don't Lie  

Lee introduces a self-audit process that goes far beyond asking friends what they think about you. While trusted feedback remains valuable, she suggests examining two areas that reveal your true priorities: your calendar and your bank account. These documents tell the unvarnished story of where you actually invest your time and money, often revealing surprising disconnects between stated values and lived reality.

The calendar audit exposes how you really spend your time versus how you think you spend it. Lee gives the example of someone claiming to be deeply spiritual who rarely makes time for prayer, meditation, or spiritual community. Similarly, many people describe themselves as entrepreneurial go-getters while their calendars show little investment in professional development, networking, or skill-building activities. This disconnect sends confusing signals to potential partners about who you really are.

The financial audit proves equally revealing. Lee challenges listeners to examine their spending patterns over the past six months, looking for evidence of the values they claim to prioritize. Someone who says they value health and fitness but spends more on dining out than on gym memberships or healthy food reveals a gap between aspiration and action. These patterns matter because they shape the energy you bring to relationships and determine whether you'll attract someone who shares your stated values or your actual lifestyle.

Lee recommends conducting these audits quarterly, treating them as opportunities for course correction rather than self-criticism. The goal isn't perfection but rather increasing awareness of the messages you're sending through your daily choices. When your time and money align with your stated values, you begin attracting people who naturally fit into the life you're actually building rather than the life you wish you had.

Discovering Your Three Core Values  

After completing the self-audit, Lee guides listeners through identifying their three core values—not ten, not five, but exactly three. This limitation forces difficult choices and ensures that your values are specific enough to guide daily decisions and relationship choices. Lee explains that many people struggle with this exercise because they want to claim every positive quality as a core value, but this dilutes their personal brand and makes it harder to attract aligned partners.

The process requires distinguishing between aspirational values and current values. Lee acknowledges that some of your three values might represent who you want to become rather than who you are today, and that's acceptable. The key is being honest about which values currently drive your decisions and which ones you're committed to developing. This honesty prevents you from attracting people based on future promises rather than present reality.

Lee uses freedom as an example of how values translate into lifestyle choices. Someone who truly values freedom will structure their career, finances, and relationships to support flexibility and autonomy. This might mean choosing freelance work over traditional employment, building multiple income streams, or seeking partners who also prioritize independence. The value becomes evident in countless daily decisions, from travel planning to career moves.

The three-value framework also provides a filter for relationship decisions. Lee suggests keeping your values private during early dating stages, using them instead as an observation tool. Rather than announcing your values on the second date, watch whether potential partners naturally demonstrate similar priorities through their actions and choices. This approach helps you identify authentic alignment rather than getting involved with someone who's simply telling you what they think you want to hear.

Here's Lee's recommended process for identifying your core values:

1. Initial brainstorm: Write down all values that feel important to you

2. Group similar values: Combine related concepts (like honesty and integrity)

3. Rank by decision-making: Which values actually influence your major life choices?

4. Test with scenarios: Imagine difficult situations and see which values guide your responses

5. Narrow to three: Force yourself to choose the three that matter most

6. Live them daily: Look for ways to express these values in small, consistent actions

Energy Over Appearance: Why Your Vibe Matters Most  

One of Lee's most striking insights centers on energy versus appearance in dating success. While many people focus extensively on physical presentation—the right outfit, perfect makeup, designer accessories—Lee argues that your energy communicates far more about who you are than your external appearance ever could. People sense your emotional state, confidence level, and core values through subtle cues that have nothing to do with how much you spent on your wardrobe.

This energy reflects your relationship with your stated values and your level of self-awareness. Someone who's genuinely living their values radiates a different kind of confidence than someone who's trying to project an image that doesn't match their reality. Lee explains that this authentic energy attracts people who appreciate substance over surface, while superficial presentation often draws those who prioritize appearance over character.

The concept extends beyond first impressions to relationship sustainability. While physical attraction might create initial interest, the energy you bring to daily interactions determines whether someone wants to build a life with you. Lee emphasizes that this energy stems from alignment between your values, actions, and self-presentation. When these elements match, you naturally attract people who are drawn to your authentic self rather than a carefully constructed persona.

Lee warns against the common mistake of broadcasting your values too early in relationships, which can come across as performative rather than authentic. Instead, she recommends letting your energy and consistent actions demonstrate your character over time. This approach attracts people who appreciate your actual qualities rather than those who are simply responding to your marketing pitch about who you claim to be.

Take Control of Your Dating Destiny  

The personal branding approach to dating offers a refreshing alternative to endless swiping and hoping for the best. Lee's methodology requires more upfront work than traditional dating strategies, but it produces more sustainable results by addressing the root causes of attraction patterns rather than just the symptoms. When you align your daily actions with your core values and project authentic energy, you naturally begin attracting people who complement your actual life rather than your fantasy version of it.

Start your personal branding transformation today by conducting Lee's self-audit process. Pull out your calendar and bank statements from the past three months, and honestly assess where your time and money go. Ask two trusted friends to describe your energy and presentation without sugarcoating their feedback. Then begin the work of identifying your three core values and reverse-engineering your daily habits to support them.

Remember that this process takes time and requires ongoing attention. Personal branding isn't a one-time fix but rather a continuous practice of aligning your actions with your values and projecting authentic energy in every interaction. The investment is worth it because when you attract people who appreciate your genuine self, you build relationships based on substance rather than surface-level chemistry. Your future partner—that king or queen you've been seeking—is likely looking for exactly the authentic, aligned person you're becoming through this work.

Want to keep learning about relationships after 50? Subscribe to the "Love Lately" podcast with Lee and Ron Rogers. Each episode tackles real issues like communication gaps, rekindling romance, and creating lasting bonds during life's second chapter. Join their growing community by leaving comments on their episodes – they specifically mentioned how much they value listener feedback. Find "Love Lately" on your favorite podcast platform and make their straight-talking relationship advice part of your weekly routine.

Connect with Lee Roger:

LinkedIn: @leviticawatts

Website: Lee Ashby Rogers

Youtube: @LeeAshbyRogers

Instagram: @mrs_lee_rogers