It’s okay, dating isn’t supposed to feel easy
It’s exhausting sometimes. Emotionally, sure, with the ghosting and the “I’m not ready for a relationship” conversations and trying to translate what that one prompt on their profile actually means about their beliefs about women in the workplace.
But there’s also the pure logistical component - hoofing it to a new wine bar after work, wondering whether you’ll be wishing you were at home watching The Summer I Turned Pretty about ten minutes later. Planning your workout schedule around which days you need to wear your hair not in a messy bun later that day.
You want to be in a relationship - it’s a part of your life that hasn’t clicked into place yet and you still definitely want it to. But it’s feeling harder and harder with how this whole dating process is affecting your life.
It’s normal, my dear, to be frustrated. I wish the dating landscape were simpler and less challenging to navigate but this is where we are. But make no mistake, you’re not doing something wrong that’s making it so hard specifically for you.
That craving you have, for the videos about how to navigate certain situations or where to meet interesting people, often boils down to searching for some sort of shortcut to your end result. It’s totally human but it’s also steering you in the wrong direction.
Why you should stop looking for dating shortcuts
It feels like if we just had the right script, the right platform, the right timing, everything might finally fall into place. But I found in my own dating life, if I got a little curious in those moments, the moments where I was Googling that new dating app that’d been blowing up my adds on TikTok or overanalyzing how long to wait before texting back, I’d notice that what we’re really searching for isn’t an answer at all.
We’re searching for a way to make dating easier.
And there’s nothing wrong with wanting things to be easier! Humans are wired to seek certainty and control because it signals to the ancient survival part of our brain that we’re safe. Simple processes like they talk about in psychological studies are appealing to our brain: mouse hits lever, gets cheese. Especially when it comes to something as close to our heart as our dating and relationship life, we want to know that if we put in the effort, we’ll get the reward.
But I think we can all agree that dating is full of uncertainty, questions and disappointment. Even the strongest women (and men!) feel the sting of not being chosen, of being ghosted, of investing energy that goes nowhere. That’s why it’s so tempting to look for hacks or rules or shortcuts that can give us even the tiniest modicum of peace of mind that we’re on the right track. If there’s a way to outsmart the discomfort, why not try?
Social media and advice culture make it even harder. Everywhere you look there’s a headline promising the one thing you need to know or the three secrets to finding love fast. It gives the illusion that the right tactic will eliminate risk and pain and frankly, they drive clicks and views in a way that benefits the person making them.
Here’s the truth: those shortcuts are surface-level solutions. They might tell you which app has the best user base or give you a clever opening line, but they can’t change what actually matters: the inner confidence, resilience, and self-knowledge you bring to the process. For eldest daughters (and women like them), they’re particularly dangerous because they build a pattern of somebody else knowing how to do this thing, implying that the eldest daughter doesn’t actually know the way. The overachiever, box checker in us then craves a system: “Tell me what to do and I’ll do it.” But there’s no one size fits all and these bite size, surface level pieces just pull her further away from her own intuition and self-knowledge.
Wanting a shortcut is normal. It’s our nervous system’s way of saying, “I don’t want to get hurt again.” But what actually protects you isn’t finding the right app or the perfect line. It’s knowing you can handle whatever happens.
The Problem with Trying to Make Dating Easy
The promise of “easy dating” is seductive: If I just do this right, I won’t get hurt.
But the paradox is that trying to avoid discomfort often makes dating harder.
Think about it. If you’re afraid of rejection, you might hold back from showing genuine interest. If you’re afraid of saying the wrong thing, you might rely on scripts that feel stiff instead of natural. If you feel like you need to get support and guidance from someone else in order to do things “right,” you don’t believe that who you naturally are is enough.
That’s a problem.
It is one of my most fundamental beliefs that while there is chance involved in dating, there is also a very significant factor of the energy with which you enter the situation that influences your outcome. Influences, not decides.
If you are in the people pleaser “pick me” energy, you are far more likely to end up in a situation where you find someone who is comfortable taking and not giving.
If you are in the “all men suck” energy, you are far more likely to see plenty of evidence of this and further harden the walls around your heart to prevent yourself from further frustration.
Is it possible to feel a little insecure and meet someone amazing? Absolutely. That’s what I mean by influence, rather than decide. We are all human with parts of ourselves we love and parts that aren’t our favorite so I don’t think there’s a single person currently in a relationship that had no insecurities when they met their partner. But the energy that you go about dating with can make it more likely that you meet great people and connect with them, or less likely depending on your approach.
The approach of trying to find a way to make dating feel easier - to avoid disappointment, frustration and rejection - the more I think you’ll find dating harder. Here’s why…
People might ghost even when you’ve done everything “right.” The person who seemed so aligned on paper may still fade out. Trying to make dating easier is trying to control the unpredictable and frankly, things outside of your control.
So while you try the tips and tricks to reduce ghosting, frustration and uncertainty, you’re going to fail, and that’s going to make things feel even worse.
We have to accept that dating is a process that we are very much not in control of. As an eldest daughter control freak, this is annoying, I know.
Discomfort is the Path to Confidence
“Focus on loving yourself and then the right person will walk right into your life.” When I was single, hearing this advice made me want to throw a wine glass at a wall. Partially because it suggests that how I showed up determined the timing of when the right person walked into my life. As I’ve just explained, I think our energy can influence what type of people we meet but this type of advice just felt factually incorrect because what I did couldn’t guarantee that a few days following reaching this elusive state of “loving myself” that Prince Charming and I would match on Hinge.
And yet, I knew there was some truth to the advice. The more secure I felt in myself, the more attractive my energy was and the more I’d be able to handle rejection or disappointments with resilience.
It seemed like confidence was the way to get our of discomfort - either I’d find somebody or the rejections wouldn’t bother me as much.
But in my years of my own personal development and then in offering advice and resources to other women now for years, I’ve discovered that this is completely backwards.
Feeling confident doesn’t make us hurt less when we get ghosted or rejected. It doesn’t eliminate uncertainty or insecurities. Real confidence doesn’t make it so we never feeling uncomfortable. It’s a belief in yourself that you can handle the discomfort and uncertainty when it shows up.
If you can sit with the discomfort of rejection, you also build the capacity to sit with the discomfort of intimacy. Because closeness is uncomfortable too (just ask me in the first 6 months of my current relationship - holy emotional growth challenge). Vulnerability, commitment, being truly seen, those things bring up just as much fear as being ignored or rejected.
Think of it like strength training. No one builds muscle without resistance. The weight feels heavy, your muscles tremble, and it’s uncomfortable. But that’s exactly what makes you stronger. Dating is the same: each time you sit with the discomfort and move through it, you’re building emotional resilience.
That resilience is part of confidence. It’s building your belief: “No matter what happens today, I’ll be okay.”
Why These Skills Will Help You Be a Great Partner Too
Here’s the good news: the very skills that carry you through the ups and downs of dating are the same ones that make you ready for a healthy relationship.
Accepting yourself as you are.
Regulating your emotions instead of spiraling.
Communicating clearly and with kindness.
These aren’t just strategies for surviving dating. They’re the foundation for building something lasting with another person. Not to mention navigating all the parts of life.
Every awkward first date, every disappointment, every moment you choose authenticity over performing, it’s all practice. When you focus on what dating can teach you rather than trying to get through it as quickly and efficiently as possible, you’re not just increasing your chances of finding someone. You’re preparing yourself to be the kind of partner who can sustain love when you do.
So instead of seeing dating as a frustrating test you have to pass, think of it as an opportunity to refine your self-image, what you’re looking for in a partner, and your emotional regulation skills. You’re building the muscles that will carry you into a relationship where both people can show up fully.
Three Things to Focus On Instead of Shortcuts
So if shortcuts don’t work, what actually helps? Here are three areas to focus on that will transform not just your dating life, but your confidence and relationships as a whole.
1. Building Confidence in the Value You Bring
Your worth isn’t determined by whether someone swipes right, texts back, or asks for a second date.
Confidence starts with recognizing that you bring value into every interaction simply by being who you are. That value isn’t tied to being perfect, looking a certain way, or never making mistakes. It’s tied to your presence, your perspective, your capacity to connect.
Practical ways to use dating to grow:
Intentionally notice the parts of yourself you believe a future partner will like and appreciate. Celebrate your strengths and the ways that things go well for you. We don’t need to second guess what’s already going well.
Use the experience of dating to shine a spotlight on areas that are more tender and sensitive. These areas of insecurity are inviting you to take a deeper look. Often, they are far more loveable than you realize and spending your non-dating time addressing how you are still loveable even when these things are true can open up significant growth and healing.
Separate from the outcomes. Break the patterns of determining the reaction of someone you just met on a dating app as any sort of indicator of your value. This can start with silly pep talks about the many disastrous things you may have discovered about them if y’all had kept dating to show yourself why their opinion doesn’t matter. But on the deeper level, the more you realize that the individual reactions are full of chance based on their mood, what they’re looking for, etc. and entirely out of your control, the more you’ll build a healthy separation between your self-worth and the outcome of a specific date.
Confidence isn’t about getting the desired results. It’s not contingent on whether the guy chooses you! Confidence helps you stay so grounded in your value that whether they do or not, you remain steady.
2. Managing Difficult Emotions
If dating stirs up anxiety, doubt, or fear of rejection, congratulations, you’re human. The goal isn’t to eliminate those feelings, but to learn how to move through them without letting them run the show.
Start with awareness. When an uncomfortable emotion hits, pause and notice it. Name it: “I feel anxious. I feel disappointed. I feel insecure.” Simply naming emotions helps reduce their intensity.
Then practice regulation:
Breathe slowly to calm your nervous system.
Journal to process thoughts instead of spiraling.
Offer yourself the same compassion you’d extend to a friend.
Emotional resilience doesn’t mean rejection stops hurting. It means rejection doesn’t immediately take the wheel of your day or week when it happens.
This is important because even when you find someone you want to build a relationship with, you will still experience moments of uncertainty, rejection or insecurity. It might be in the context of the relationship (like you bring up something that matters to you and your partner dismisses it) but it’s still there.
So your ability to feel those emotions without spiraling and developing tools and skills to keep the train on the tracks even when triggered will serve you both in dating and in ther rest of your life.
3. Belief Systems About What’s Out of Your Control
Yes, we have to accept that a big part of dating is out of our control. But a big part of life is out of our control.
For eldest daughters, there can be hidden belief systems running through every part of your life:
“If I’m not working my hardest, everything will fall apart.”
“If I don’t do it, nobody else will.”
“I always need to have it all together.”
“My feelings are too much for most people.”
“If I can figure out what they’re looking for, they won’t leave.”
You can probably see how these might have developed in childhood and early adulthood but are not creating problematic patterns in your dating life. Addressing these larger beliefs can help dating feel less triggering and make dealing with uncertainty less overwhelming.
How to feel confident on a first date and beyond
Let’s accept that dating isn’t supposed to feel easy. It’s vulnerable, requires effort and is mostly out of our control.
Our confidence on that first date, and the next one cannot be determined by whether the last first date led to a second. Life is full of uncertainty, rejection and doubt.
The ability to show up with an open heart and an open mind cannot depend on knowing that things will work out because, well, you’re not God and we don’t know the outcome yet.
Building your foundation on belief in yourself, belief that you can handle uncertainty and disappointment and belief that even if it’s a short term disappointment it’s a learning in service of a long term love story, is a much stronger place to be.
There is no shortcut to intimacy. There is no hack that will guarantee safety. But you don’t need one. What you need is trust in yourself: trust that whatever today brings, you’ll be able to handle it.
Because that’s what real confidence is. And that’s what will carry you not just through dating, but into the kind of partnership you’re ultimately looking for.
