Put an End to Your Chronic Dating Disappointment


There’s this awful thing that happens when you’re single.

You get really excited about someone new, and then…they aren’t your person.

Then you get excited about a different someone new, and then…they still aren’t your person.

Then you date this totally different, equally exciting, someone else new…

And you really thought they might be your person?

But then…they still aren’t your personnnn?!?!

WT ACTUAL F. Where is your damn person??

When this keeps happening all you feel is disappointed and disappointed and then more devastated and disappointed.

Sometimes it sucks the grossest, hairiest of donkey balls to be riding this ride that is “pursuing a beautiful, committed, fulfilling, healthy, happy relationship”.

Especially when you are in the business of not settling, and you know what you want, and you know the quality of connection you desire and deserve, and you can’t accept or tolerate less than that anymore.

The disappointment can be so real.

Until now, biotch bebez.

I’ve uncovered that there are THREE PRIMARY INGREDIENTS to combatting the flagrant disappointment factor that is often served as a side dish to so many single folks, and I’m sharing them today.

Here’s what you need to do like right now if you officially wanna get off this ridiculous emotional roller-coaster that is 21st century dating:

1. Lower your damn expectations.

People often confuse this with “LOWER YOUR STANDARDS” which I would never, in any volume of years, recommend.

Lowering expectations just means coming to terms with the fact that most people you date will not be a good match for you. Like, 90% of the people you date. Seriously. 9/10 folks aren’t even going to be close. And then 1/10 might be close, but still not quite right.

So with these numerical facts in mind please consider:

How much are you building up any one date? Or just one conversation? Or just one match on one dating app?

How much are you building up and getting crazy excited about some new person (often based on very little info)?

How intense are your burning hopes for the kind of relationship you wanna have with some newbie, especially when you are in the beginning stages of budding connection?

We all know how it tends to go: You get a little excited about someone, or have a few fun text conversations, and suddenly you're wondering where you guys will vacation together next summer. Or whose house you'll go to the holidays for. OR WHAT YOUR ADORABLE BABIES WILL LOOKS LIKE.

This sounds a bit bonkers-sauce but most of us do it. And in the act of doing so, we are inflating our expectations. Like big, fat, Thanksgiving Day parade balloons of doom and gloom.

So please get in the habit of popping those balloons, babe.

Learn to lower your expectations.

You don't know if you're going to have a lifetime of happiness with this person, or even 2 hours of enjoyable conversation, or a few dates of enjoyment before you discover what makes them undateable. There could be a million ways in which this thing WON’T WORK OUT and you will have zero adorable babies with them.

If this sounds pessimistic, it's not. It's realistic.

Realism is something most people need to practice when it comes to their excitement and attraction towards new people.

It’s about not getting crazy caught up in the hopes and expectations you have, and instead, remaining neutral and welcoming towards whatever outcome occurs.

If you have a good time together? Cool, you'll see them again and just keep getting to know one another. Nice and expectation-free and easy-like.

If you don't have a good time together? Cool, you won't see them again and will find other people to get to know. Nice and expectation-free and easy-like.

Rinse, repeat, don’t stress about it.

2. Have lots of fun on your own as a single person.

If you are sorta loathing every aspect of your solo life, of course you're going to be obsessed with the idea of a new person or the right relationship rescuing you from your woes.

And of course any time that new person isn't your partner-person, you're going to feel as though you’re being relegated back to this jail cell of misery that is your single life.

I’ve had icky seasons of my own single life where it felt that way, so I know how shitty it feels. You're lonely/unhappy/empty-feeling, then you get a cutie on the horizon and everything perks up and gets happy and glow-y for a bit, then things don't work out and you're back to the lonely/unhappy/empty-feeling stuff.

It’s like you're on this terrible yo-yo ride, where most of your joy and satisfaction is based on someone wanting to be with you…simply so you get to feel less alone.

So if you wanna hop off the yo-yo ride, you have to start building a solo life that is fulfilling and satisfying.

You have to commit to the terrifying concept that you…here…alone…might be it forever… So you have to find some ways to legitimately enjoy it.

BREATHE INTO THAT FOR A SECOND: YOU. HERE. ALONE. FOREVER. If that terrifies you, you have to work to do.

This can feel like the most impossible thing when you’re in the habit of focusing all your attention on your next amazing romantic relationship…but it’s also the work most people know they need to be doing, but are avoiding like the plague (at least that’s what I did for a very long time! #goodcompany).

Start putting efforts into building a solo life that is deeply meaningful to you. This typically includes exploring hobbies or interests that light you up. Choosing a career that at least somewhat aligns with your purposes and values. Creating meaningful connections. Making fun plans. Having things you are really looking forward to. Setting goals and slaying them.

It also includes doing whatever inner work you need to do to heal the very common, very painful, human issues that might be plaguing you (uncomfortable self-esteem stuff, anxiety, stress management, existential dread, FOMO, thinking everyone hates you, etc etc).

But maybe most importantly? NUMERO TRES:

3. Honey, ya gotta have faith.

"Faith" tends to get a bad wrap because people think it means you need to pray every night, or buy into the idea that some giant puppeteer-man in the sky is pulling strings to make shit happen (or not happen) in your life.

If that works for you, yay. Work it. Keep praying to the big puppet-man. #bless

If that doesn't work for you, I invite you to consider that Faith is simply choosing to believe that (in the long-term) life is working out in your favor, even when (in the short-term) it seems like your shit is super jacked up and nothing is going right.

Faith is about looking at the numerous instances in your life where you were very worried, scared, frustrated, or fearful, and noticing how many of those situations got resolved.

Most of the time, given enough time, things tend to work out.

Sometimes things work out even against our will — like we painstakingly dig, and search, and pry for the answer/solution, and then boom! The shitty stuff seems to get solved without us having to actively, painstakingly, fix everything (because hellooo, it’s impossible for any one person to fix everything).

Think about it: There was a time where you were deeply confused and eventually received clarity.

You didn't know what to do, and then you slowly realized what you needed to to do.

You were super freaked out about something, and then discovered you had no real reason to be super freaked out after all.

That’s how most of life happens. And that’s especially how most relationships tend to work themselves out.

You have no idea how many conversations I’ve had with women who were really sure they were fucked in the love department.

They came into our initial sessions staunchly asserting that they didn’t really believe in love anymore, that they were simply too broken to make anything work, that men were trash-swine, that their jerk-off father had screwed them up for life, that they had no reason to believe that anything would work out…

And then weeks or months later, after we’d been working together for some time, they’d start seeing someone awesome and realize WOW - GREAT LOVVE IS POSSIBLE! They weren’t totally FUBAR’d after all!

Or maybe a year after our work ended, I’d receive an email sounding like this:

“I can’t believe I’m saying this but oh my gosh - I met the most amazing guy. He’s everything I’ve been looking for, like even better than I imagined. And it’s been so easy! We just clicked and it wasn’t complicated and now we’re talking about moving in together. My Mom loves him and I can’t believe I was so worried. It all worked out! You were right…it all worked out…you’re a complete genius and I owe everything to you. We’ve already decided we’re going to name our first-born ‘Amy’ in your honor…”

Okay so I’m paraphrasing and taking a a couple liberties at the end there…but THE SENTIMENT STANDS TRUE.

It all worked out.

Most of the time, it all works out.

And in the end, we realize we had nothing to be worried about in the first place.

This continuous self-reminding ("Things tend to work out...I don't need all the answers right now...maybe this will all be okay eventually…") is what Faith actually is.

It's a practiced belief in your own well-being in the world, in this life, in the grandest, highest sense.

And this Faith-based belief system is something we could all stand to cultivate and practice and come back to a little more often, because life can be very freak-out worthy sometimes. 

So if you’ve been on a year of going-nowhere dates, maybe that’s okay…maybe things are working out.

If you’re in the midst of a terrible awful break-up situation that you would give anything to change, maybe it will all be alright and eventually it will all make sense. Not today, not next week, but eventually.

If you’ve just been ghosted again and you’re ready to set stuff on fire and simultaneously sit-down-cry in the shower, see if any part of you can quietly believe that things are working out, even when it feels like they are definitely not.

That’s all that Faith is: Believing that things are working out even when it seems like they are not.

I don’t encourage having Faith because I’m on some pushy agenda to get you onto a spiritual path, or to get you to stop complaining so much. I encourage having Faith because it makes the day-to-day bullshit of life one million times easier to manage, and it helps us relax a bit into the delicious mystery of it all.

I also encourage this because when I look at how my life has worked out, and how so many of my clients lives have worked out, I see these trends:

Things do tend to work out in our favor, albeit in very bizarre and unexpected ways.

In the short-term everything looks like a hot mess, but in the long-term all the wrinkles get ironed out and sometimes we’re even grateful for the hot, wrinkly messes.

If you can zoom out on whatever your present frustration is, and relax into the simple idea that you really don’t have to solve everything right now, nor are you responsible for ironing out every damn wrinkle all on your own, then solutions, ease, and clarity tends to present themselves much more readily.

And that’s because Faith provides some relief.

And relief provides increased relaxation.

And relaxation makes way for calm and clarity.

And it is from a place of calm and clarity that all good ideas, inspiration, solutions, and positive possibilities are born.

When you’re clear and calm, you find yourself casually say “yes” to a random invitation to a party you might normally say “no” to, where you happen to meet this great-seeming guy with whom you have captivating conversation over hors d’oeuvres. And then 7 months later you’re at his brother’s graduation party telling the random, delightful story about how you met.

When you’re clear and calm you decide to download Bumble again because why the hell not, what do you have to lose, and you randomly match with this dreamy dude who shares a lot of similar interests and wants to take you pumpkin-patching this weekend. A year later you commemorate your anniversary at the same pumpkin patch, snapping pics with spiced cider in hand.

When you’re clear and calm you wander into this random coffee shop because you got lost downtown and it started raining, and the barista is FINE AF and asks if you’d like cinnamon on your latte, and you share that you’re allergic to cinnamon but thanks, and he shares that he’s allergic to garlic, and you talk about allergies for awhile and then he writes his number on your cup and winks at you, wishing you a great day. THEN Y’ALL GET MARRIED AND MAKE THOSE ADORABLE BABIES.

This is how life happens. Unexpected. Randomly. By magical happenstance. It can’t be predicted or forced or manufactured or planned. It never is. Faith is about accepting that and knowing that letting go a little bit and learning to love what you cannot know yet.

Now doesn’t that sound better than pretty much every other alternative??

So in short, here’s a quick recap for eliminating the dreaded cycle of dating disappointment:

Lower your expectations. Have lots more fun as a single person. Practice having some Faith.

I’m so curious (if you’re keen on leaving a comment): Which of these ingredients could you stand to increase in your own single lady life?

Amy Young19 Comments