Why does dating feel so hard?
You know that feeling when you're getting ready for yet another first date, staring at your reflection and wondering why something that should feel natural feels so impossibly complicated? You're not alone in this. We've all been there, scrolling through dating apps at 11 PM, wondering if we're doing something fundamentally wrong or if dating has just become this weird, exhausting performance that nobody really enjoys anymore.
The desire to find love is pretty universal. You'd think the world would work like some magical matching system, sorting through possibilities until we find someone worth investing in. We should be able to move through connections until we find our person without feeling like we're constantly failing some invisible test. But here we are, collectively wondering why something so basic to human experience feels so damn hard.
Which is why today we're diving into the real reasons dating feels like an uphill battle and what we can actually do about it.
The hidden struggles that make dating feel impossible
As eldest daughters who've been in the trenches of modern dating, we've noticed some patterns that keep showing up. It's not just you, and it's not just bad luck. There are some very real dynamics at play that make dating feel way harder than it needs to be.
We're all performing instead of being ourselves
Let's be honest about what happens on those early dates. We become slightly more polite versions of ourselves, a little less sarcastic, maybe more patient than we actually are in real life. We might dress more feminine than usual, stay out later than our preferred bedtime, or pretend we're totally fine with splitting the check when we'd actually prefer not to.
These adjustments feel harmless, even strategic. We tell ourselves we're just putting our best foot forward. But here's the thing: we're all sitting across from each other, presenting these carefully curated versions of ourselves that aren't actually real.
Now, we're not saying you should show up to a first date in your rattiest sweatpants (though honestly, if that's your vibe, own it). There's definitely value in presenting yourself thoughtfully. But if you're a tomboy who never wears dresses, don't convince yourself you need to squeeze into one to be worthy of love. Not only are you showing this person an altered version of who you are, but you're also screening in people who might not actually be compatible with the real you.
The goal isn't to trick someone into liking you. It's to find someone who genuinely likes who you actually are. And that requires showing up as yourself, even when it feels scary.
Our founder, Samantha, spent a year as a digital nomad, testing out different cities she might want to move to. She was initially scared that being mobile and not knowing where she might want to live would make it so that nobody wanted to date her. But she showed up honestly, sharing this part of her story in chats before the dates or on first dates themselves. What she quickly observed were that people who found travel interesting or valued an independent person saw it as a “pro” not a “con.” She ended up meeting someone on one of these dates who became her long term partner because they had in common a desire to travel, appreciating a flexile lifestyle and many other things that never would have come up if she hadn’t been open about who she really was.
We're treating dating like a numbers game instead of connection
Somewhere along the way, we started approaching dating like it's a workout routine. Show up, put in the reps, and eventually you'll see results. But dating isn't like lifting weights. There's no inevitability that if you go on enough dates and check enough boxes, you'll find your person.
Many of us keep ourselves at arm's length until we see something we like enough to open our hearts. We're screening for specific qualities, waiting for someone to prove they're worth our emotional investment. But this approach creates a Catch-22: we're only making ourselves available to people who check our predetermined boxes, potentially missing unexpected but better fits.
You might be thinking, "But I already know what I want! What's wrong with having standards?" And look, having standards is important. But if your current system isn't working, if you're frustrated by how few people feel like genuine fits, it might be worth examining whether your walls are so high that you're missing real connections.
The truth is, a lot of us are walking around dating while being emotionally unavailable. We're physically present but not actually open to being surprised, challenged, or changed by the people we meet.
We're terrified of disappointment and rejection
Here's the uncomfortable truth: dating is hard because it's vulnerable. Our emotions get involved, and it's almost inevitable that we'll get hurt sometimes. But avoiding hurt isn't the goal of dating. Finding genuine connection is.
It's like baseball. You have to accept that you'll strike out sometimes if you want any chance of hitting a home run. But if we live our dating lives focused on minimizing strikes, the most effective strategy is to never swing at all. And then we wonder why we haven't hit any home runs yet.
There has to be risk to get what we're looking for. The fear of rejection keeps us playing it so safe that we never actually put ourselves in a position to be chosen for who we really are.
The pressure to have it all figured out
As eldest daughters, we're used to being the ones with the plan. We've spent our twenties excelling at work, going to therapy, learning to communicate better, and generally doing all the "right" things. But dating doesn't follow the same rules as career advancement or personal development.
We can't optimize our way into love. We can't create a five-year plan for finding our person. And this lack of control feels deeply uncomfortable for those of us who are used to being able to figure things out through effort and strategy.
The pressure to have our dating lives as together as the rest of our lives creates this weird performance anxiety. We feel like we should know exactly what we want, how to get it, and how to navigate every interaction perfectly. But dating is messy and unpredictable, and that's actually part of what makes it beautiful.
Why modern dating culture makes everything harder
Beyond our individual patterns, there are some larger cultural shifts that have made dating more complicated than it used to be.
The paradox of choice
Dating apps have given us access to more potential partners than any generation in history. Sounds great in theory, right? But all that choice can actually make us less satisfied with whoever we're with. There's always the possibility that someone better is just a swipe away.
This abundance of options can make us more critical, less willing to work through normal relationship challenges, and constantly wondering if we're settling. It's harder to be present with someone when part of your brain is always scanning for upgrades.
The commodification of romance
Somewhere along the way, dating started feeling more like shopping than connecting. We have lists of requirements, deal-breakers, and must-haves. We swipe based on photos and brief bios, making split-second decisions about complex human beings.
This consumer mindset makes it harder to see people as full, complicated individuals worthy of curiosity and patience. Even though, we’re complicated individuals who would want grace, curiosity and patience from our partners. In the early days of dating, we can easily get trapped in this idea of evaluating whether someone meets our specifications, rather than exploring whether there's genuine chemistry and whether this is someone we see the potential to build something with.
The loss of organic meeting opportunities
Our grandparents met at work, through friends, at church, or in their neighborhoods. They had built-in contexts for getting to know people gradually, seeing how they interacted in different situations, and developing feelings over time.
Now, we're expected to determine romantic compatibility with strangers over coffee, often with no mutual connections or shared contexts. It's a lot of pressure to put on a single interaction, and it doesn't mirror how relationships actually develop in real life.
There are many young people (and heck, people of all ages) rebelling against this trend, consciously seeking out IRL opportunities to meet people. This is awesome. We have to be aware the ways any of our habits and patterns might be in the way of our goals so even if your favorite nights are cozy on the couch, it might be worth considering if continuing to maintain that pattern all the nights of the week is constructive to the goals you have.
Doesn’t mean you have to radically switch to being an “out at the bar” person. Can you find a cozy bookstore in your area to go read at more regularly? Can you plan a cozy mountain weekend with friends where you’d naturally end up exploring breweries? You can keep the vibe but try it in new places.
What actually helps: a different approach to dating
So what do we do with all this? How do we navigate dating in a way that feels more authentic and less exhausting?
Focus on connection over evaluation
Instead of going into dates with a mental checklist, try approaching them with genuine curiosity. What's this person's story? What makes them light up? How do they handle conflict or uncertainty? What do they find funny?
This doesn't mean lowering your standards or ignoring red flags. Focus on being present enough to actually get to know someone before deciding whether they're worth your time.
Practice emotional availability
Being emotionally available doesn't mean being vulnerable with everyone you meet. It means being open to being affected by the people you encounter. It means allowing yourself to be curious, surprised, or even challenged by someone new.
This requires some risk. You might develop feelings for someone who doesn't feel the same way. You might discover that someone you thought was perfect actually isn't right for you. But this openness is what allows real connections to develop.
Redefine cuccess
What if a successful date wasn't one that led to a second date, but one where you showed up authentically and learned something about yourself or another person? What if the goal wasn't to find your person as quickly as possible, but to become the kind of person who can recognize and appreciate genuine connection when it appears?
This shift in perspective can take so much pressure off individual interactions and help you approach dating with more curiosity and less anxiety.
Trust your instincts
As eldest daughters, we're often so focused on being "good" at dating that we ignore our own gut reactions. We override our instincts in favor of what we think we should want or what looks good on paper.
But your instincts are valuable data. If someone makes you feel anxious or small, that matters, even if they check all your boxes. If you feel genuinely comfortable and curious around someone, that matters too, even if they're not your usual type.
Frequently Asked Questions
Q: How do I know if I'm being too picky or not picky enough?
A: This is such a common concern, and honestly, it's the wrong question. Instead of focusing on whether you're too picky, ask yourself: Am I being authentic about what actually matters to me versus what I think should matter? Am I open to being surprised by people who don't fit my usual pattern? The goal isn't to have the "right" level of pickiness, but to be clear about your actual values and open to unexpected connections.
Q: What if I keep attracting the wrong type of person?
A: This usually points to one of two things: either you're not being clear about your boundaries and values, or you're unconsciously drawn to people that replicate familiar patterns from your past. If you grew up in a household with parents who emotionally withdrew whenever you had big feelings, you might notice a pattern where you meet people you like but as soon as you ask for support from them, they pull away. If you always felt like you did something wrong as a kid, you might accidentally end up in situations where you feel that it falls apart because you screw something up. Getting clear on how the patterns in your dating life might reflect deeper emotional patterns can help you unlock the ways to shift your baseline belief more towards what you want to feel.
Q: How long should I give someone before deciding if there's potential?
A: There's no magic number, but we generally recommend at least three dates if there's no obvious incompatibility. First dates are often awkward, second dates can still feel performative, and third dates are where people usually start to relax into themselves. That said, trust your gut. If someone makes you feel consistently uncomfortable or uninterested, you don't owe them more time.
Q: Is it normal to feel exhausted by dating?
A: Absolutely. Dating requires emotional energy, vulnerability, and constant decision-making. If you're feeling burned out, it might be time to take a break and reconnect with what you actually want, rather than what you think you should want. Sometimes the best thing you can do for your dating life is to step away from it for a while.
Q: How do I stay hopeful when dating feels discouraging?
A: Remember that finding the right person isn't about going on the most dates or having the most options. It's about becoming clear on who you are and what you want, and then being open to recognizing it when it appears. Every disappointing date is data about what doesn't work for you, which actually brings you closer to what does.
The real work of dating
Here's what we've learned after years of navigating modern dating: the real work isn't about becoming more attractive, more interesting, or more dateable. It's about becoming more yourself.
The people worth your time will be drawn to your authenticity, your quirks, your particular way of seeing the world. The people who aren't won't be, and that's actually a gift. It saves you both time and heartache.
Dating is hard because it asks us to be vulnerable with strangers, to risk rejection, and to stay open to possibilities we can't control. But it's also one of the most human things we do. It's how we find our people, build families, and create the relationships that sustain us through life.
The goal isn't to make dating easy. It's to make it authentic. And when you approach it from that place, even the challenging parts start to feel more meaningful.
