Why does dating feel like work?

You're not imagining it—dating really is harder now

For the most part, I love dating. But sometimes? Man, does it feel like work. Unpaid labor that I have to do after my real job, which is literally talking, writing, and teaching about love and dating.

I'm good at dating. I better be because I've been putting in the reps for a long time. I'm not a serial monogamist; my pattern is long stretches between relationships. When I'm single, I date to meet people, have fun, and have sex, but ultimately, I'm looking for someone I want to be in a committed relationship with.

I've been on a lot of dates. You also frequently share your dating disasters with me. Through my own experience and years of watching this space, I've developed a good understanding of why most of us struggle.

Do I look like I’m working?

Recently, I asked my subscribers what makes dating feel like work. Their responses were honest:

"Being ghosted after I thought we had a connection." — Elizabeth

"Lack of effort tied with lack of follow through. Actions need to align with words. You can't create trust and safety in a relationship without that foundation." — Rebecca

"People don't read profiles, so you end up asking the same questions over and over again." — Ebony

I want to share why dating feels so challenging right now. Maybe it'll help you feel less alone in it—and give you a different way to think about the whole thing.

"Dating apps are trash."

I hear this constantly, and I don't think it's true. People want to blame the app, but that's like blaming your car for bad driving.

Dating apps are just a tool to put you in front of other single people. Yes, they gatekeep features behind paywalls, which is annoying. But I don't buy the conspiracy that they want to keep you single to keep you paying. The apps don't keep you single—people keep themselves single.

The problem isn't the app. It's how we use them.

Some people swipe for ego validation, collecting matches to stroke their ego or soothe their souls, but never actually meet anyone. Others overthink every profile, looking for red flags that might not be there. But the biggest issue I see? The endless quest for someone better.

Here's how it goes: You match with someone decent. You go on a date. Maybe they eat funny or don't make lots of eye contact (they must be emotionally unavailable!), and instead of getting curious about this real human in front of you, you write them off. Back to the app you go, swiping for the next "upgrade."

You can do this for years before realizing that some of those people you dismissed were lovely to get to know. But by then, you've trained yourself to see dating as shopping instead of connecting.

Meeting people in person is hard.

We've forgotten how to talk to strangers. This is wild because this is literally how humans found love for thousands of years before 2012.

Your parents met in person. Your grandparents met in person. Everyone before them figured it out without swiping left or right. However, we've allowed that muscle to atrophy.

Now, the idea of approaching someone at a coffee shop or striking up a conversation at a bookstore feels terrifying. We've convinced ourselves it's creepy or outdated when we're just out of practice.

Meeting someone in real life means you have to read social cues, start a conversation, figure out if they're single, and if there's mutual interest, ask them out. All without the safety net of knowing they're on an app looking for dates.

It requires putting yourself out there in a way that feels completely foreign now. But here's the thing: it's still the most natural way to meet someone. We've just scared ourselves out of trying.

The fear of rejection is paralyzing.

Fear exists to keep you safe, but sometimes it keeps you too safe. Your brain can't tell the difference between a saber-toothed tiger and someone saying "no thanks" to coffee. Both register as threats.

Somewhere along the way, maybe in middle school, maybe last year, you learned that rejection hurts. So your brain decided it's better not to ask than to risk that pain.

But here's what happens: You see someone cute at the gym. You think about saying hi. Your brain immediately floods you with worst-case scenarios. What if they think you're weird? What if they're already in a relationship? What if they laugh? So you don't say anything.

You choose the guaranteed outcome (nothing) over the uncertain one (possible connection, possible rejection).

The problem is that rejection is an inevitable part of life. Some people will say no, and that's OK. Just like you're allowed to say no to others, you want people who aren't meant for you to reject you kindly. Not everyone is meant for everyone, and that's good news.

But most of us would rather stay small and safe than risk the temporary sting of someone not being interested. And that's how you end up single and wondering why you can't meet anyone.

We're burnt out and barely keeping up.

We're working too many hours, not getting enough sleep, and trying to afford a life that keeps getting more expensive. Self-care gets squeezed between the second job and grocery shopping if you're lucky.

So you're hustling to pay rent, managing kids or aging parents, pleasing bosses who expect more of you than ever, and somehow, you're also supposed to have the energy to find love? I'm tired just thinking about it.

Dating is inherently inefficient. Whether you're spending hours swiping through profiles or getting dressed up for dates that go nowhere, it's going to take time you don't have and money you need for other things.

When your time is precious, it's easier to spend it on guaranteed returns: the gym, friends who already love you, kids who need you, or hobbies that recharge you.

Plus, how are you supposed to show up excited and curious on a first date when you're running on four hours of sleep and wondering if you can afford the Uber home? It's hard to be charming when you're calculating whether drinks will put you over budget.

Dating requires emotional bandwidth that most of us are already spending elsewhere.

And if you’re over dating and want to learn how to enjoy single life, you might love this post:

People have stopped trying.

Some people just aren't putting in effort anymore, and it shows. Poor communication, vague answers about what they want, zero follow-through on plans—it all adds up to feeling like you're the only one who cares about finding something real.

The bar is already low. You don't need elaborate dates or grand gestures. But showing up clean, present, and genuinely interested in getting to know someone should be the absolute minimum. Yet somehow, people are limbo-dancing under even that.

I get why this happens. Everything I've described above makes it tempting to phone it in. Why invest energy when someone might ghost you? Why be vulnerable when the next person is just a swipe away? Why plan thoughtful dates when you're exhausted and broke?

But here's the thing: if you're someone who wants to date with intention and care, you're stuck in a pool of people who've decided that caring makes you a sucker. You end up doing all the emotional labor, carrying on conversations, suggesting plans, and following up, while they coast on your effort.

It's exhausting to be the only one trying to build something real when everyone else is just trying to get through the date.

And you wouldn’t be alone. Here’s what some of my subscribers are struggling with:

"Lack of intellectual curiosity. Unmatched effort. The inability to be a 'full on adult.'" — Marissa

"Lack of authenticity." — Linda

You're not imagining it. Dating feels harder than it used to. But recognizing these patterns is the first step to navigating them differently. The good news? You're not broken, and neither is love. The system needs some work. And you could probably use a gentle kick in the pants, too.

My favorite quote on this subject is:

“Each of you is perfect the way you are ... and you can use a little improvement.”

―Shunryu Suzuki

You’re doing great, and you could use a little work.

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If this resonates with you and you're ready to approach dating differently, I'm hosting 'Drama-Free Dating: Have Fun While Meeting Cute People' on Saturday, June 14th. It's a 2-hour workshop where we'll cover how to make dating feel fun instead of like work, plus a full hour of Q&A for your most pressing questions. You'll also receive the recording if you're unable to attend live.

We're talking about building rejection resilience, meeting people both online and in real life (IRL), and shifting your mindset so that dating becomes an adventure instead of an audition.

General admission is $49, but paid subscribers receive it for $39. New to my Substack? You can subscribe for $7/month and still receive the workshop for $39 instead of $49 (you’ll get the discount code in the welcome email) —plus, you'll gain access to all my more intimate articles, which are exclusive to subscribers.

Ready to stop making excuses and start making moves? Summer's here, people are out and about, and love is waiting for you. Let's get it.

Note: This is a one-time mini-course; I won't be offering another live session at a later date. Everyone will get the recording after the session is over. Keep it as long as you’d like.