Dating Won’t Necessarily Feel “Easy”, Despite What Your Coupled Friends Say

You Can Date Better
8 min readJan 22, 2024
Photo by Nick Fewings on Unsplash

“It should be easy.”

I can almost feel the panic rising up in my clients after hearing something like this from a satisfied, well-meaning coupled person. When you find the “right one,” they tell them, “you just know.” It shouldn’t be “hard”.

Hmph. These people are obviously not dating and relationship experts.

Nothing confounds me more than daters believing there is one pathway to success when looking for love. If we look to our parents, or our best friend, or, Cupid forbid, the plethora of fantasy rom-com stories for what the pathway is supposed to look like, we will absolutely limit ourselves to the possibilities.

Talk to enough people about their love stories and you start to uncover a very comforting — and maybe confusing — truth: It’s different for everyone.

For some people, meeting their person might have felt easy, and for many, many others, it was not so easy. Sometimes, it’s a rollercoaster of ups and downs between the journey to meet them, the meeting itself, the dating period until they decided to be exclusive and maybe especially the hard stuff they might deal with after it seemed so “easy”. Cue the nightmare sister-in-law!

One of the tenets of my coaching practice is that there is no right way to find your person, outside of staying true to yourself and your values.

Not only that, there is no “right” way to feel when you first meet them to know for sure… this is it. Love stories come in all different timelines, and a huge mistake many daters make is thinking they can choose how their story will play out. Sure, most people want an adorable story and first date magic, but does it matter if that happens if you end up finding your true partner in the end?

What does “easy” mean?

Easy might mean you literally feel at ease in the presence of that person. It’s like you’ve known each other forever and making decisions about them or the relationship isn’t hard at all. In fact, making plans is effortless and drama free, right from the start!

That would be nice. However, expecting all people to know if a person is right for them by instantly feeling at ease with a stranger is total nonsense. I do want you to get along, like you love and care for each other — eventually. I want you to be able to communicate with total trust and comfort — eventually.

It’s okay if it takes time to trust and warm up to someone. It’s okay to have nerves on a date and learn, through experience, that you feel at ease with someone. For many couples, that feeling is earned over time… and that’s okay.

Easy might also mean that it didn’t take much effort to meet them — it just “happened.” Yeah, yeah, sure— we’ve all heard this one. You’ll meet them when you least expect it! Just stop trying and it will come to you!

Okay, stop. This is not reality for a good proportion of people. To be sure, putting effort into meeting people is not always easy, but reaps many benefits, and since the majority of couples are meeting online now, this “stop trying” adage is obviously moot.

Yes, at some point, and in some sense, I want it to feel easy for you. Relationships shouldn’t constantly feel like a struggle. Although, I would argue that sometimes it takes a little work to make things easy. And that’s totally okay.

What’s not so easy?

Well, online dating, for one. Even when someone finds their person through an app, they generally talk about the difficulties of the process, with plenty of setbacks and unsettling stories along the way.

Even a first date with a stranger, for example, is filled with reasons that you might not feel at ease quite yet — the greatest of which is that you might be nervous about expectations and have a natural sense of self preservation. Some folks need time to build trust in order to feel that sense of security.

Speaking of security, let’s talk about dating in the circles you have now. “Why can’t I just meet someone at work, like a normal person?” I hear sometimes. Is that so easy? Because I think dating through friends or work is actually pretty socially risky, although very convenient. There are conflicts of interest, and if doubts that arise during the relationship, it usually ripples out beyond just the daters themselves. If things go wrong, the fallout can be complicated, create rifts, or create unnecessary hardship that lasts longer than needed. Ouch.

Maybe embrace the hard. Dating can have a lot of difficult challenges that are overcome by the building of a good connection over time — distance, love language differences, conflict navigation, and time constraints are all things that might not spell doom for a couple if they choose to work at it because they feel the connection is right.

In fact, working through things that are not easy could be a great way to see how a couple navigates problems together — how’s that for a dating mind-bender?

Does “easy” mean it’s love?

Nope. It’s also not necessarily a long-term love connection just because there is a sense of ease. There are multiple cognitive biases at play that push the narrative of this, especially if “love is easy” is the story we want to believe.

Something feeling “easy” might mean you are going to be great friends. It might mean you get along great, but have different visions for partnership. It might mean someone is very, very charming. It might mean two people were just having a great day that particular day, with the perfect mindset to have a date.

The truth is — plenty of these “easy” feeling first dates fizzle out. It’s just one small part of a larger picture. Sometimes it works out, sometimes it doesn’t.

Many wonderful, long-lasting relationships don’t feel easy on the first date… or the second, or even the third. Many successful couples only felt friendly feelings or were even a little turned off on date one, but decided — against their gut feeling — to give it another shot.

Do the “easy” ways of meeting people mean something? Nope. That’s just an easy part of their love story. And here’s the catch:

All of these stories contain struggle of different kinds. The most successful couples I know that say things like “it was easy” when they met each other still had a lot of differences they had to navigate throughout their courtship and/or marriage. Sure, some aspect might have felt easy, but it doesn’t mean their mother-in-law wasn’t a nightmare to deal with or that their partner’s habit of leaving their clothes on the floor didn’t drive them crazy. It didn’t mean that their partner was perfectly beautiful, made tons of money, or had the right politics and religion. It’s a bit of that hindsight being 20/20 thing more likely.

And I have the success stories to prove it.

Easy Evidence

I want to give you a bunch of gifts and lessons learned from real stories with real people that found love without it being easy.

  1. One of my relatives met her husband in college. Wow, so easy, right? Just fell in her lap! But they did not get along at first — at all. They would frustrate each other, and argue about things, and had you asked her the first year they met if she would marry him, she would have likely given you an uproarious NO! They’ve been married over 20 years now. Happily. “Easily” in some ways, given how well they compliment each other. But it was hard won at first.
  2. I met my partner while dealing with a terribly embarrassing health concern and it affected our sex lives — like, for a while. I was also working 60 hour weeks while in grad school, and felt like I was going to pass out at some point most days. Also, my grandpa died. Also, my cat died. Also, we lived an hour away from each other. Easy?! Are you friggin’ kidding me?! At first, this was so very hard. But we just kept at it and the one thing that was easy was our communication around what was hard. I’m still thankful for that.
  3. A dear friend met her husband while he was still unhappily married to someone else and she was in a lackluster committed relationship. Did they feel easy around each other at first? Certainly. The feeling was overwhelmingly right. Was this an easy situation to navigate? Definitely not. Heartbreakingly hard, but with an extraordinary love on the other side.
  4. Another dear friend met her husband after a series of disastrous boyfriends, and dating was so easy in comparison. Right from the start, they both had clear communication around what they were looking for, how much they liked each other and the pathway felt very “right.” Voila! No problems! Totally easy! Their first year of marriage? So friggin’ hard. All of that easiness didn’t spell bliss until they got some stuff worked out. Sometimes, hard stuff pops up where you least expect it.
  5. Is paying for dating apps easy? Is paying for dating events easy? Is paying thousands of dollars for matchmaking easy? All those events are how plenty of people meet these days, and for many, that investment and the pressure that comes with it is hard.

The list goes on — is working on yourself easy? Is maintaining a positive mindset easy? Is keeping your past fears from encroaching on your future dates easy?! HECK NO!!! The majority of my clients don’t necessarily feel it’s easy when they’re dating, even when they meet their person. They look back and think, yeah — that was kinda hard. But it should, at the very least, get easier… when you connect with the right person over time.

What I’m here to assure you of, is that just because one happy couple tells you it was easy for them, it doesn’t mean that’s the gold standard. It’s easy for them to believe that’s the key to success because it worked for them.

Some folks will meet their partner in college. Some folks will meet them on an app after years of trying. Some move halfway across the country to be with their love, and others meet them down the street. Some put a lot of effort into going on numerous dates over years with lots of different people, and others meet their person after two weeks of trying online dating for the first time.

Partnership and love happen in all kinds of ways and we are not the deciders of how our storyline unfolds. Your story might be very different from the one you want. Trust me that the pathway to love is not always easy. It might not be storybook, and that’s okay.

I think it’s more fun when it’s not boring, frankly. Give me a “we hated each other at first” story any day!

Change the way you date. Get a coach. Get dating.

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You Can Date Better

Writing/content curation by Carrie Prince, founder & boss lady behind — coaching & consulting for the current online dating landscape.