Why Modern Dating Feels So Exhausting (and What You Can Do Differently!)

It’s a Friday night and you’re winding down by scrolling through your phone, swiping past potential matches. With each swipe, you feel a twinge of frustration, maybe even a sense of hopelessness creeping in. You start wondering if you’ll ever find someone who truly “gets” you, or whether dating has become pointless altogether. The excitement that online dating once promised now feels like an exhausting cycle of quick chats, ghosting, and short-lived connections. If this is you, you’re not alone. More and more people are finding themselves caught between the convenience of modern dating and the disillusionment it can bring.

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The landscape of dating has changed dramatically in recent years, something I’ve noticed both in my therapy practice and in conversations with friends and colleagues. It seems to show up in sessions with clients who feel frustrated o

r overwhelmed by dating, and in my personal network, where the pressure to swipe, match, and move quickly is palpable. I’ve always felt a bit conflicted about it. On one hand, online dating apps and “speed dating” events offer undeniable convenience, efficiency, and the excitement of endless possibilities. On the other hand, the very tools designed to help us connect can sometimes turn the process of truly getting to know someone into a rushed, almost transactional experience.

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I’ve found myself resonating deeply with Esther Perel’s observations about modern dating. In her article “Why Modern Love Is So Damn Hard,” the way she articulates the tension between constant connection and persistent isolation really hits home! She notes that modern dating often emphasizes instant gratification and novelty, leaving many of us feeling more disconnected even as we’re “more connected” than ever. Reading her thoughts made me pause, because I see this play out not just in my clients’ experiences, but also in my own social circles. Perel talks about how, as our communal institutions give way to heightened individualism, we increasingly look to our partners to meet needs that used to be shared across communities emotional support, physical closeness, validation, and a sense of belonging. It’s no wonder that dating can feel so high-stakes and exhausting; the pressure to find someone who can meet so many needs is enormous!! Her perspective helped me put words to a feeling I’ve long sensed, that in our rush to connect, we often lose sight of the slower, deeper process of truly knowing someone.

This is such a vast topic to delve into, and I certainly don’t pretend to have all the answers! But in my work with clients (and honestly, in my own reflections too), I’ve noticed a few of the common barriers I see people facing when it comes to modern dating.

Managing Expectations

A common barrier I see is the invisible “checklist.” Many people go into dating with an idea of who their partner should be, what they look like, what job they have, how quickly sparks fly. But when real life doesn’t line up with that fairy tale image, dating can feel discouraging and even hopeless. Instead of focusing on perfection, try shifting toward curiosity: What could unfold if I gave this connection a chance to grow, even if it doesn’t look like a movie script from day one? Part of managing expectations in modern dating means releasing the pressure for a relationship to fulfill every wish, dream, or desire. A healthy partnership isn’t meant to complete you, it’s meant to support and comfort you, to offer a sense of safety where both people can be themselves.

Rather than approaching dating with a mental checklist (i.e. what they do for work, how tall they are etc.), it can be more meaningful to focus on shared values. For example, ask yourself: Do we see the world in ways that align? How do they treat people around them? Can I imagine feeling emotionally safe with this person? These kinds of questions tend to reveal much more about long-term compatibility than the surface-level traits that often dominate early dating conversation.

The Pressure to Perform

First dates often feel like interviews, with both people trying to present the “best” version of themselves. It’s completely natural to want to be liked, but sometimes this effort leaves you wondering later if you were truly seen or if you were just performing. Showing up authentically, even if it feels vulnerable, is what creates the foundation for a genuine connection.

This doesn’t mean oversharing every intimate detail of your life or trying to lay your whole heart on the table at once. It’s more about staying aligned with your values and letting your true self come through in small, meaningful ways. Maybe it’s expressing your curiosity, sharing a personal passion, admitting when you’re nervous, or simply responding honestly to a question. When you allow yourself to show up in ways that feel safe and true, you create space to feel comfortable in your own skin—and invite the other person to meet you as you really are. That ease and authenticity often matters far more than saying the “right” thing.

The Fear of Wasting Time

Modern dating apps move fast, which can lead to the pressure of needing to know right away whether someone is “the one.” But meaningful relationships often don’t reveal themselves instantly. Instead, they tend to grow slowly and steadily, in small moments of connection. Giving yourself permission to let relationships unfold at their own pace can take away some of the anxiety around dating.

I often remind clients that time spent getting to know someone is never wasted. Even if it doesn’t lead to a long-term relationship, every encounter offers something valuable such as insight, clarity, a chance to practice vulnerability, or simply an opportunity to learn more about what feels right for you. You might walk away realizing how good it felt to be fully yourself in a conversation, or notice patterns that help you grow for next time.

So maybe instead of asking, “Is this going somewhere?” after every coffee or dinner, try asking, “What did I learn about myself in this experience?” or, “Did I show up as the person I want to be in relationships?” That small shift can turn the process from anxiety-filled to something far more empowering and compassionate.

Asking the Right Questions

The kinds of questions we ask, both of ourselves and of our dates, can really shape how we experience connection. I often notice that many people approach dating like a quiet checklist in their heads: "What do they do for work? How tall are they? Do they want kids? What kind of car do they drive?" These are all understandable questions, especially in a culture that teaches us to look for compatibility through surface-level traits. But when we focus too much on whether someone “checks all the boxes,” we can miss what’s actually unfolding in the moment.

Instead of only asking, “Do they fit what I imagined?” try shifting toward questions like, “How do I feel in their presence? Do I feel safe, respected, and comfortable being myself?” or “Do our conversations leave me curious and grounded, or anxious and unsure?” These reflections can tell you far more about the potential for emotional connection than any résumé-like detail ever could.

I’ve had clients share that when they started paying more attention to how they felt on a date rather than what the other person said or did “on paper,” something shifted. Dating began to feel less like a test and more like a conversation, a mutual exploration rather than a performance. When we approach dating with curiosity rather than evaluation, it opens space for authenticity on both sides. You might find yourself laughing more, asking better questions, or simply feeling more at ease. And that’s often where the most genuine connections begin.

In closing, I want to acknowledge that modern dating can feel exhausting and at times, even hopeless. But it really doesn’t have to be! Each date, each connection, and even each disappointment can offer insight into who you are and what you value most. When you approach dating as an opportunity to show up authentically and stay true to your values, it becomes less about finding “the one” and more about finding yourself in the process. And that, in itself, is always time well spent.

Reference:

Perel, E. (n.d.). Why Modern Love Is So Damn Hard. Retrieved from https://www.estherperel.com/blog/why-modern-love-is-so-damn-hard