Why does dating feel harder than ever—even though we have more ways to meet people than any generation before us?
Dating apps have given us more options, more conversations, and more opportunities to meet someone. Yet so many people feel exhausted, discouraged, and stuck in a cycle of disappointing dates, almost-relationships, and uncertainty.
In this video, psychotherapist and connection expert Jenn Pinkerton explores why modern dating can feel so overwhelming and what may actually be happening beneath the surface. Instead of simply telling you to “date more,” Jenn challenges the way we approach finding love and shares three shifts that can completely change how you date.
You’ll learn why having more options doesn’t necessarily lead to better choices, why constantly evaluating potential partners can keep you from truly getting to know someone, and why curiosity is often a healthier dating strategy than looking for instant certainty.
Jenn also explores the importance of becoming a healthy relational partner—not just finding one. Because healthy relationships aren’t simply discovered. They’re built by two people who are willing to communicate, grow, repair, and create emotional safety together.
Whether you’re single, actively dating, recovering from a disappointing relationship, or wondering why finding lasting love feels so difficult, this conversation will help you stop dating harder and start dating healthier.
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