What if the moment that feels most uncomfortable on a first date is actually the moment that tells you everything you need to know?
Many people enter dating determined to avoid conflict. They smile through uncomfortable conversations, overlook comments that don’t sit right, or convince themselves they’re being “easygoing.” Especially for those dating after 40 or dating after divorce, staying agreeable can feel like the safest way to protect themselves from rejection or disappointment. But this habit often prevents people from discovering whether someone is truly capable of building a healthy relationship.
In this solo episode of Practicing Love, I reveal the third move in my series on transforming modern dating. While the first two episodes focused on creating an honest atmosphere at the start of a date and staying connected to your own experience throughout the conversation, this episode explores what to do when something doesn’t feel quite right.
Most people respond to uncomfortable moments in one of two ways. They either smooth things over and pretend nothing happened, or they emotionally check out of the conversation without saying a word. Although both reactions are understandable, neither helps you learn whether the person sitting across from you can handle honesty, curiosity, and emotional intimacy. Instead, Shana encourages listeners to do something surprisingly simple: acknowledge what you’re experiencing.
Rather than accusing your date or making assumptions about their intentions, she recommends expressing your own internal experience. A sentence as simple as, “Can I say something honest?” followed by sharing what you noticed in yourself can completely transform the conversation. This isn’t about creating conflict or turning a first date into therapy. It’s about inviting authenticity.
When you honestly express a small moment of discomfort, your date’s response becomes valuable information. They may become curious, defensive, dismissive, or open. Every response reveals something about their emotional maturity and their ability to navigate real relationships.
Drawing from years of coaching experience, I share the story of a divorced client who repeatedly invested months into relationships before discovering important incompatibilities. By practising this simple shift, he learned to recognize emotional availability within the first hour of meeting someone instead of months later. The goal isn’t to test people or create uncomfortable conversations for their own sake. It’s to stop performing and start discovering.
Together, the three shifts in this series create a new approach to dating—one rooted in honesty instead of approval, curiosity instead of performance, and genuine connection instead of self-protection. Rather than hoping love happens by chance, you begin creating the conditions where authentic intimacy can grow.
Who is this episode for?
This episode is for anyone who struggles to speak up during dates, avoids uncomfortable conversations, or repeatedly finds themselves discovering incompatibilities months into a relationship. Whether you’re dating after 40, returning to dating after divorce, or simply looking to build healthier, more authentic relationships, this episode offers a practical communication tool that helps reveal compatibility much earlier.
Why do people avoid uncomfortable moments on first dates?
Most people believe that keeping conversations light and avoiding awkwardness makes them more attractive. They worry that expressing discomfort will make them seem difficult, overly sensitive, or confrontational. Thus avoiding uncomfortable moments on first dates.
What should you do when something feels off during a date?
Instead of ignoring the feeling or silently withdrawing, Shana recommends acknowledging your own experience.
A simple phrase like: “Can I say something honest?” creates space for an authentic conversation without placing blame on the other person.
Rather than saying, “You’re being dismissive,” you might say: “When you said that, I noticed I became a little quiet.”
The difference is significant. You’re sharing your own experience rather than making assumptions about someone else’s intentions. This invites curiosity instead of defensiveness and often leads to a much deeper conversation.
What are the three dating shifts Shana James recommends?
Throughout this four-part series, Shana introduces three foundational practices for creating honest, meaningful dating experiences:
- Create a shared intention at the beginning of the date. Instead of trying to impress one another, invite honesty from the start.
- Replace the question “Do they like me?” with “Do I like who I’m being in this conversation?” This keeps your attention on your own experience rather than seeking approval.
- Speak honestly when something feels uncomfortable. Share your experience with curiosity instead of judgment to discover how the other person responds.
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 spiralling, minimizes post-date overthinking, and allows you to leave interactions with greater clarity and confidence.
Where can I find Shana James and learn more about Practicing Love podcast?
Shana James is a relationship and dating coach and the host of the Practicing Love podcast. Shana James’ recent book is called Honest Sex: A Passionate Path to Deepen Connection and Keep Relationships Alive. You can find her at her website and follow her on Instagram.
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