Why the Hell Is Dating So Hard Now?

Dating in your 40s is weird.

There. Blog post done.

Okay, maybe I have a few more thoughts.

I've been thinking about dating quite a bit lately. Not because I've been going on a ton of dates. Quite the opposite, actually. I've gone on exactly one date since becoming single again.

One. So clearly, I'm crushing it.

But between dating apps, conversations with friends, my own experiences, and watching relationships around me, I keep coming back to the same question: Why the hell is dating so hard nowadays?

I'm not even sure dating itself is the problem. Maybe it's everything we've built around it: algorithms, subscriptions, social media, filters, endless scrolling, endless swiping, texting, Snapchat, ghosting, bots, and the illusion that there's always someone better waiting one more swipe away.

All of this technology was supposedly going to make it easier for us to find each other. Somehow, I think we may have made it harder.

When Is the Right Time to Start Dating Again?

That's a question I've thought about a lot.

After my first divorce, I waited quite a while before I started dating again. Looking back, I still wasn't ready. I thought I was, but I needed more time to heal, move on, figure out who I was again, and prepare myself for whatever the next chapter looked like.

My second divorce was different. We had lived more like roommates for a long time. The personal connection had been gone for quite a while, so emotionally, the ending felt different.

I actually created a dating profile while the divorce was in its final stages. By then, the relationship was over, we were sleeping in separate rooms, and I was basically waiting on the house to sell, lawyers, paperwork, houses to be built, and all the other logistics that come with untangling a life.

Could I have waited until every signature was on every piece of paper? Absolutely. But honestly, I wasn't really looking to jump into another relationship. I was curious more than anything. What was dating like now? Who was out there? Had anything changed?

Spoiler alert: Everything changed.

Even now, I'm not rushing. I've been on one date. I'm not trying to fill some giant void in my life, and I'm not desperately searching for someone because I can't stand being alone.

There is no void to fill.

I'm looking for someone I can blend a life with. Someone who brings peace, support, love, curiosity and a willingness to build something together.

That's really all I can ask.

Apparently finding that person now requires approximately 17 dating apps and a small business loan.

Dating Apps Are Basically a Car Payment

When the hell did dating become so expensive?

Download an app, create a profile, upload six pictures, and answer a bunch of prompts about your perfect Sunday, dream vacation, favorite activity, whether pineapple belongs on pizza, and probably what fictional character you'd invite to dinner.

Great. Now pay us.

Want to see who liked you? That'll cost you. Want to really like someone? That'll cost you more. Want your profile to actually be shown to people? Ohhhh, have we got a premium upgrade for you!

At this point, I'm pretty sure it would be cheaper to rent a billboard along the interstate:

Single. Two kids. Employed. Has house. Likes to travel. Please inquire.

Then there's creating all these damn profiles.

I'm a software engineer. Can we please get some SSO for dating apps?

Seriously. Let me create one master dating profile, authenticate with OAuth, and propagate my profile across every dating platform simultaneously.

Name? Joel. Age? Forty-something. Kids? Two. Looking for? Relationship. Hobbies? Photography, traveling, hiking, technology, writing, and apparently filling out dating profiles.

Save. Sync to all. Done.

A bunch of these apps are owned by the same handful of companies anyway, which makes having to recreate everything even more ridiculous.

And then I have another question: Are these apps actually showing us everyone?

I have no idea. If you're charging me money to tap a digital heart on someone's picture, how do I know the algorithm isn't intentionally holding people back to keep me scrolling?

Maybe the love of my life lives three miles away. Maybe she's on the app right now. Maybe the algorithm wants another $14.99 before we're allowed to know each other exists.

Congratulations, You Found a Human!

Then comes the next adventure: figuring out whether the person on the other side of the screen is actually a person.

I've encountered profiles that seemed completely legitimate. Great pictures. Similar hobbies. Good conversations. But you can only be pen pals for so long.

At some point, I want to hear your voice. Let's FaceTime. Let's have a phone call. Eventually, let's actually meet.

I had one conversation that seemed promising, but every attempt at video chatting came with an excuse. Fine, I get it. Life is busy. Eventually, I tried a good old-fashioned phone call through the app.

Apparently that was rude.

Calling someone. On a dating app. Where we were supposedly trying to get to know each other.

WTF. Seriously?

Then there are the conversations that feel almost too good. Send a message at 1:00 a.m.? Instant paragraph. 7:00 a.m.? Instant paragraph. Middle of the workday? Instant paragraph. Every answer is perfectly written and seemingly tailored to exactly what you wanted to hear.

Either I've found the most responsive woman in North America...

or somewhere a server rack is falling in love with me.

Then, when you finally feel confident there's an actual human being on the other end of this internet phone-on-a-string, you encounter the opposite problem.

Silence.

“Hi 👋”

You liked me, I liked you. We matched… Fantastic!

And now...

“Hi 👋”

Oh, Good talk…

I understand people are busy, especially at this stage of life. We have careers, kids, houses, family obligations, sports, activities, custody schedules, dogs, travel, and meetings about meetings. Life is busy.

I don't expect someone to sit around staring at her phone waiting for Joel to send another riveting message.

But if you liked someone and you're genuinely interested in them, don't you want to learn something about them?

Ask questions? Tell stories? Be curious?

That's one of the biggest things I'm looking for now: interest. Not constant attention. Not 75 texts every day. Not someone telling me where she is every second. Just genuine, reciprocating interest.

I want to learn about your family, your kids, your passions, your childhood, your goals, the places you want to see, and the things that make you laugh. And I want someone who wants to learn those things about me.

I'm not looking for a one-night stand, and I'm not interested in hookup culture. I admit intimacy is important.

But substance is the foundation.

If neither of us is curious about the other person, what exactly are we doing here?

And Please, for the Love of God, Not Snapchat

Another thing I've discovered is that people like to meet on dating apps and immediately move the conversation somewhere else. That part I understand.

But Snapchat?

No thanks.

I'm a 40-something-year-old man. Give me your phone number. Text me. Call me. FaceTime me.

I'm not adding you on Snapchat so we can communicate like we're trying to keep our parents from finding out we're dating.

I have a mortgage. I'm not maintaining a Snap streak.

WhatsApp? Fine. I understand that one. But ultimately, I want to move away from apps.

Dating app → phone number → phone call → meet.

You know...

Dating.

Yes, Looks Matter

Here's another thing we apparently aren't supposed to admit: physical attraction matters.

Maybe that makes me shallow. I don't think it does. I'm a photographer. I'm a visual person. Of course I notice a beautiful smile, nice hair, someone who takes care of herself, and someone I could picture bringing home to meet my family.

That's human. What I think is shallow is when looks become the entire foundation.

But while we're talking about pictures, what the hell are we doing with some of these profile photos?

Filters everywhere. Skin processed until you look like a wax museum exhibit. Fake freckles. Butterflies floating around your head. Snapchat effects all over your face.

Ladies...

You're not fooling anyone.

My original iPhone took better pictures than some of these profile photos.

And eventually, assuming this goes well, I'm going to see your actual face. So maybe we could start there.

Once attraction gets my attention, though, I actually read the profile. Do you like traveling? Hiking? Family? Photography? Do you have passions? Did you actually answer the prompts in a way that tells me something about you? Do your values, faith, and morals align with mine?

Because I'm not looking for someone exactly like me. And that's something I've learned over the years.

Apparently Dating Comes With Acronyms Now

Dating profiles have also taught me an entirely new vocabulary.

ENM. Poly. DINK.

At some point, I feel like I'm going to need a glossary just to figure out whether I'm compatible with someone.

ENM? Ethical non-monogamy. Poly? Multiple romantic relationships. Open relationships?

Apparently there's a whole world out there I knew very little about.

No judgment. Adults can build whatever kind of relationship works for them.

But no thanks.

I already have kids, a career, a house, dogs, hobbies and approximately 17 dating apps I'm trying to keep track of. I don't need a relationship that requires its own organizational chart.

Maybe I'm old-fashioned, but if I finally find someone I really want to be with, I don't like to share.

I'm having a hard enough time finding one person I genuinely connect with. Some of you are out here successfully maintaining two or three relationships?

Honestly, I'm not even offended. I'm impressed.

But still...no thanks.

You can have your people. I'm looking for my person.

Then there's DINK: Dual Income, No Kids.

Well...

I already screwed that one up about 15 years ago.

Twice. 😂

My boys aren't going anywhere, nor would I want them to. So if someone's dream is a permanently child-free, dual-income lifestyle, I'm probably going to be a disappointing addition to that plan.

Although once these boys are grown and off the payroll, I would like to formally apply for DIK status.

Dual Income. Kids moved out.

I don't think that's a real acronym.

But it should be.

I Don't Need You to Like Everything I Like

I used to think compatibility meant having the same hobbies. I don't anymore.

Sure, having some common interests helps. I'd love someone who enjoys traveling, hiking, being outside and exploring somewhere new. But you don't have to love everything I love. You don't even have to understand why I love everything I love.

Just care that I do.

Be curious about it. Support it. And I'll do the same for you tenfold.

I want someone with passions of her own. Teach me something. Show me something I've never done. Take me somewhere I wouldn't have gone myself.

Relationships shouldn't require two identical people. They should involve two people interested enough in each other to occasionally step into the other person's world.

Maybe I don't love your hobby.

But I love watching you love it.

That's different.

I Don't Need Someone to Complete Me

This one is important.

I hear people talk about finding someone who “completes” them. I don't want that.

I don't think another person should be responsible for making you happy. You should be capable of being self-sufficient. You should have your own interests, passions, friends and goals. You should be able to appreciate your own life—the good and the bad.

I don't need someone to complete my life.

I want someone to complement it.

There's no void I'm desperately trying to fill. I have two incredible boys, a career I love, a home I've worked hard for, family, photography, travel, creative projects, a dog, faith and friends.

I’m happy where I’m at.

What I'd like is someone who looks at all of that and thinks:

This is pretty great. Mind if I sit beside you?

Someone who brings peace, support and love. Someone who brings a feminine touch to a house occupied by three males, because God knows we could probably use it.

I'm not looking for someone to come cook for us.

I want someone to come cook with us.

Grab whatever random crap is left in the refrigerator and let's figure out dinner together. Let's clean together, plan a vacation together, sit around a backyard fire, walk the dogs, go hiking, stay home on a Friday night, or take a ridiculous spontaneous road trip.

Let's come up with some stupid side-hustle ideas that we can dream of together.

I want a teammate. Not because either one of us needs the other person.

Because we choose each other.

My Boys Are Part of the Deal

Dating as a parent adds another entire layer.

My boys aren't a footnote in my life. They're part of the equation. Always.

I have them every other week, which actually gives me a pretty healthy separation between dating and being Dad. And I want to keep it that way for a while.

My kids don't need a revolving door of women coming into their lives while I figure out whether a relationship is going anywhere. They've already been through enough change. If I meet someone and eventually things become serious, then absolutely—I want her involved.

But until then, dating can remain mine.

That's also one reason I'd actually prefer meeting someone who has children. Parents understand.

Sometimes the kids come first. Plans change. Schedules are ridiculous. Someone has practice. Someone gets sick. Someone forgot about something they were supposed to tell you three days ago.

That's life.

And honestly, I like the idea of someday being a “step” figure to someone else's children. Not replacing their father. Never. Just another adult in their lives who loves them, supports them, shares experiences with them and hopefully provides another perspective when they need it.

Of course, blended families bring their own challenges.

Because apparently dating in your 40s wasn't complicated enough already.

Can We Go Back to High School?

Sometimes I secretly wish dating still worked like high school or college.

Think about it. We were basically forced into dating opportunities without realizing it. Every day, somebody locked hundreds of similarly aged people inside a building together for eight hours.

For free.

You met friends. You talked. You learned who people actually were. You saw how someone treated other people. You developed crushes. You knew their friends.

There wasn't an algorithm involved.

School was basically one giant singles event with algebra.

Now?

That'll be $49.99 a month, please.

Social Media Hasn't Exactly Helped

This is where I think the problem gets bigger than dating apps.

Social media has given us this strange perception that everyone else's life is perfect. Perfect marriages, perfect vacations, perfect houses, perfect bodies, perfect kids and perfect careers.

Except we're usually seeing the highlight reel.

Pull back the curtain and we have absolutely no idea what's happening.

And I say this as someone who genuinely loves social media. I love sharing my travels. I love photography. I love writing. I create YouTube videos because I genuinely enjoy teaching people things. Technology is a huge part of my life.

I don't think social media is inherently bad.

But there is a massive difference between using technology and being consumed by it.

Scroll through someone else's vacation, house and relationship long enough, and eventually we start wondering if maybe we're missing something.

Dating apps feed the same instinct.

Swipe. Swipe. Swipe.

She's great...

but maybe the next one is better.

Then the next one. And the next one.

Maybe the grass is greener somewhere else.

Or maybe we need to water the place we're already standing and watch what grows around us.

Put the Damn Phone Down

Being present doesn't mean technology disappears. That would be pretty hypocritical coming from me.

I love technology. But I don't want to endlessly consume online content.

I want to create it.

And here's the thing: if you want experiences worth sharing, you have to actually experience them first.

Put the phone down. Watch the sunset. Have the conversation. Walk the trail. Sit beside the fire. Cook dinner. Get lost somewhere. Laugh. Be bored together.

There's nothing wrong with taking the picture. Trust me, I'm probably going to take the picture.

But then put the camera away and actually live inside the moment you just photographed.

I want someone who understands that.

You Can't Make Old Friends

Conversation might be the thing I miss most about how relationships used to develop.

Actual conversation.

Not emojis. Not carefully constructed texts where tone can be completely misinterpreted. Sit down and talk. Talk about anything. Talk about everything. Disagree. Ask questions. Learn. Change your mind occasionally.

Tell me stories.

There's a Ben Rector song called Old Friends that I love. The idea behind it is beautifully simple:

You can't make old friends.

There are people in our lives who remember versions of us that nobody we meet today ever can. They remember what we were like as kids, what we wore, what stupid things we did, the neighborhood we grew up in, and the trouble we got into.

Those memories matter.

But here's what I think about dating now: someone new doesn't know those stories.

Yet.

So tell them.

I want to know who you were before I knew you. What did you do after school? What were you afraid of? What did your family do on Christmas? What was your first car? Who was your first crush? What did you get grounded for? What did you dream about becoming?

Hell...

What kind of roller skates did you wear around the neighborhood?

Those conversations are how someone stops being a stranger.

And maybe, eventually, they're sitting beside you years later telling that story for you because they've heard it a hundred times.

That's connection.

Apparently I've Been Giving Relationship Advice for a While

While thinking about all of this, I went back and read something I wrote nine years ago.

In October 2017, I attended the wedding of one of my good high school friends and came home reflecting on friendship, relationships and everything I'd learned up to that point.

I was divorced. My boys were much younger. And I hadn't yet met the woman who would eventually become my second wife.

I called the post My Words of Wisdom for the Newlyweds.

I gave my friends five pieces of advice: never stop dating one another; love yourself, be yourself and don't try to change each other; don't forget your roots; listen without always trying to fix everything; and finally, be present, be around and be available.

Reading those words today is...interesting.

Because nine years and another marriage later, I had two immediate thoughts.

First:

Damn. Maybe 2017 Joel was onto something.

Second:

Apparently knowing something and successfully living it are two very different things.

Maybe that's one of the biggest lessons I've learned.

Relationships don't fail because nobody has ever told us communication is important. We know. We know we're supposed to make time for each other, listen, appreciate the person beside us, put down the phone, keep dating our spouse and put effort into the relationship.

Knowing isn't the hard part.

Doing it consistently is.

Especially when life starts piling up. Careers, kids, bills, houses, responsibilities, stress and routines. Eventually, the exciting new relationship becomes everyday life.

Maybe that's exactly when all those little pieces of advice become more important—not less.

What's strange is how closely the things I wrote in 2017 match what I'm looking for today.

Back then, I wrote about loving yourself. Today, I'm saying I don't want someone to complete me. I want someone to complement a life I'm already happy living.

I wrote about remembering your roots. Today, I'm saying I want someone who wants to know the old stories—the family stories, the childhood stories, even what kind of roller skates I wore around the neighborhood.

I wrote about listening instead of always trying to fix. Today, I'm saying conversation and curiosity might be two of the most attractive qualities someone can have.

And I wrote: Be present. Be around. Be available.

That one might hit harder today than any of them.

Because now we're carrying around little computers specifically engineered to make sure we're almost never completely present. There's always another notification, another post, another video, another profile, another person, another swipe, another possibility.

Maybe the relationship advice I would give today really isn't that different from what I wrote nine years ago.

I just understand the consequences a little better now.

I've lived some more life. I've made more mistakes. I've watched relationships begin and end. I've watched people I care about lose people they thought they'd grow old beside.

And I've learned that having the right words doesn't make you immune from getting things wrong.

Maybe wisdom isn't finally figuring everything out. Maybe it's being willing to look backward, admit where you didn't live up to your own advice, learn from it, and try again.

So, 2017 Joel...

Not bad.

I probably should have listened to you a little more.

Maybe I'm a Hopeless Romantic. Or Just Stupid.

After two divorces, you'd think I'd be done.

Sometimes I wonder if I'm a hopeless romantic.

Or just stupid.

The jury is still out.

But I believe people enter our lives for different seasons. I believe God sometimes puts people in our path to teach us things we don't understand until much later.

Both of my marriages taught me things. Some lessons were wonderful. Some were painful. Some were lessons about what I needed from someone else. Others were lessons about things I needed to change about myself.

I don't regret learning them.

And somehow, after all of it, I still believe in relationships. I still believe there's someone out there.

Not a perfect person. I don't want perfect. Perfect doesn't exist.

I'm looking for understanding, forgiveness, honesty, loyalty, support, love and curiosity. Someone willing to keep learning and moving forward together.

Life Is Really Damn Short

Maybe this has been hitting me harder lately because I've watched people around my age lose relationships in very different ways: divorce, bad decisions, circumstances nobody planned for, and, painfully, death.

I've now seen several people around my age unexpectedly lose their spouses.

That changes your perspective.

Because someday isn't guaranteed. Next year isn't guaranteed.

Hell, tomorrow isn't guaranteed.

And it makes some of the games we play with each other seem incredibly stupid.

Waiting three days to text someone because you don't want to seem too interested. Being afraid to tell someone how you feel. Taking a good relationship for granted. Constantly wondering if something better is out there. Ignoring the person beside you while watching strangers live their lives through a five-inch screen.

What are we doing?

I'm envious when I see couples genuinely thriving. Not jealous. Envious. Because I think everyone deserves the opportunity to experience that kind of connection.

Sometimes people don't realize what they had until it's gone. Whether a relationship ends because of choices, because two people simply can't make it work anymore, or because God had a different plan, watching something good come to an end is hard.

So when you find someone you click with, grow with them. Learn from them. Support them. Love them.

Water the damn grass.

Because our time here is limited.

So What Am I Actually Looking For?

Take away all of it.

Delete the apps. Turn off the algorithms. Cancel the subscriptions. Get rid of the profiles. Put away social media.

No filters. No games. No bullshit.

What am I actually searching for?

A teammate.

Someone who wants to live everyday life together.

Not someone constantly waiting for the next vacation before she can be happy. I want to travel—a lot. I want to see this beautiful world.

But I also want Tuesday night to matter.

Every day can be an adventure. Sometimes adventure is getting on a plane and exploring somewhere you've never been. Sometimes it's hiking a trail you've never seen. And sometimes it's opening the refrigerator, discovering six completely unrelated ingredients and saying:

“Well... what the hell can we make out of this?”

That's life.

Relationships are hard. But I also think, in some ways, they can be easy.

Not effortless.

Easy in the sense that you're on the same team.

It shouldn't be a scorebook of I did this, you didn't do that, I make more, I cleaned last time, I planned the vacation.

Who cares?

We all have strengths. We all have weaknesses. Learn from each other. Teach each other. Help each other. Respect boundaries. Be honest. Be loyal. Love wholeheartedly.

And when life gets difficult—and it will—remember that the person standing across from you isn't supposed to be your opponent.

They're your teammate.

Apparently This Is Now My Dating Application

And I've just realized something.

This entire blog post has apparently become my application for future dating prospects.

Fantastic.

Forget six pictures and three prompts. You've now received several thousand words covering my relationship history, children, values, hobbies, communication preferences, opinions about social media, feelings about Snapchat, thoughts on blended families, theological worldview, technology habits and preferred methods of preparing leftover food.

Honestly, this might be more efficient.

For future applicants taking notes: Must enjoy some combination of travel, quiet nights, random adventures, backyard bonfires and dogs. Parenting experience preferred but not required. Curiosity is mandatory. Must occasionally tolerate excessive sunset photography.

Benefits include spontaneous trips, tech support, an unreasonable number of photographs and someone who will probably make a YouTube video explaining how to fix whatever technology problem you just had.

No cover letter required. References available upon request.

Applications are currently being accepted.

Although I'm seriously considering abandoning the apps altogether and walking around Target with business cards that say:

I find you attractive.
I'm sick of dating apps.
Here's my number.

No algorithm. No monthly subscription. No Super Like.

Maybe a QR code.

I'm still a tech guy. We can't go completely analog.

And if you're reading this because I handed you one of those cards somewhere near the Target coffee aisle...

Apparently you passed the first round of interviews.

Just please...

Don't open with “Hi 👋.”

Now I want to hear from you.

These are my experiences, but relationships look different for everyone. Maybe you're dating again. Maybe you've been married for 30 years. Maybe you've lost someone. Maybe you've screwed things up, learned some lessons, found your person, or you're still trying to figure all of this out like the rest of us.

So leave a comment below. What's the best relationship advice you've ever received? What's something you've learned that you wish you'd understood sooner? Have a completely ridiculous dating story? I definitely want to hear that too.

And if you actually met your person through one of these damn apps, please give the rest of us some hope. 😂