If you’ve ever left a date replaying every moment in your head, analyzing every text message, or wondering whether you said the wrong thing, you’re not alone. For many people, especially those dating after 40 or dating after divorce, first dates aren’t actually about getting to know someone. They’re about trying to figure out whether you’re being liked.
In this solo episode of Practicing Love, dating and relationship coach Shana James reveals the second mindset shift in her series on transforming modern dating. While the first shift focused on changing the dynamic of a date by naming a shared intention at the beginning, this episode explores the internal habit that quietly sabotages connection long after the conversation begins.
The problem isn’t always obvious. Once a date gets underway, many people naturally fall back into monitoring themselves. They start wondering: “Am I coming across well?” “Do they like me?” “Am I attractive enough?” “Did I say the wrong thing?” According to Shana, this constant self-monitoring creates a split in attention. Part of you is present in the conversation, while another part is standing outside the experience, evaluating your performance.
The result? You become less available for authentic connection.
Instead of being fully present, you’re busy reading facial expressions, decoding reactions, and trying to predict whether the other person approves of you. Even emotionally intelligent and self-aware people fall into this trap because it can disguise itself as attentiveness or empathy.
Shana explains that the question most people unconsciously ask on dates is: “Do they like me?” But she offers a much more powerful alternative: “Do I like how I’m showing up in this conversation?” That single shift changes everything.
Rather than making yourself the object of someone else’s evaluation, you become the subject of your own experience. Instead of navigating dating through self-doubt, you begin navigating through self-worth.
This perspective allows you to notice whether you’re being authentic, whether you’re genuinely enjoying yourself, and whether the connection aligns with your values. It also helps you stop performing and start participating.
Drawing from her coaching experience and examples from clients, Shana demonstrates how this question can transform shallow, frustrating dates into meaningful conversations. When people stop focusing on being chosen and start focusing on whether they’re enjoying the connection, they gain the confidence to steer conversations in more authentic directions.
The outcome isn’t necessarily a perfect date. It’s something more valuable: a real experience rooted in honesty, curiosity, and self-trust.
Who is this episode for?
This episode is for anyone who finds themselves overthinking dates, struggling with dating anxiety, or feeling emotionally exhausted after romantic interactions. Whether you’re dating after 40, returning to dating after divorce, or simply tired of constantly seeking approval, this episode offers a practical mindset shift that can help you feel more grounded and empowered.
Why do people overthink dates so much?
Most people enter dates hoping to create a connection, but they quickly become focused on evaluating how they’re being perceived. Questions like “Do they like me?” or “Am I saying the right thing?” dominate their attention. This constant monitoring creates anxiety and prevents genuine presence. Instead of experiencing the date, you’re managing it. Shana explains that real connection becomes difficult when part of your attention is dedicated to self-evaluation rather than authentic engagement.
What question should you ask yourself instead of “Do they like me?”
Shana recommends replacing the approval-seeking question with: “Do I like how I’m showing up in this conversation?”
This isn’t about judging yourself or determining whether you’re performing well. It’s about checking in with your own experience. Are you being honest? Are you expressing yourself authentically? Are you enjoying the interaction? This question helps you stay connected to yourself instead of becoming consumed by someone else’s opinion.
How does self-monitoring affect dating and attraction?
When people constantly monitor themselves, they often hide important parts of who they are. They filter their thoughts, suppress their humour, and avoid taking conversational risks. As a result, the date remains surface-level. Authentic attraction develops when people reveal who they truly are. When you stop performing and allow yourself to participate honestly, you create space for deeper conversations and more meaningful connections.
How does this mindset help reduce dating anxiety?
Dating anxiety often grows when your happiness depends on another person’s approval. By focusing on your own experience, you stop outsourcing your sense of worth. Whether the date leads to a second meeting or not, you maintain a connection with yourself. This reduces emotional spiraling, minimizes post-date overthinking, and allows you to leave interactions with greater clarity and confidence.
Previously Published on Shana James Coaching
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