Part 1: This but That — Checklists That Burn Your Dating Life

When it comes to finding your partner, it’s not a build-a-bear situation.

You Can Date Better
8 min readMar 14, 2023
Photo by Jon Tyson on Unsplash

Hefty Bag Needed

I love it when dating themes present themselves in clusters. I talk to a lot of daters day in and day out, and some weeks I’m weighted down with a particularly troubling theme that seems to be coming out of every conversation.

Lately, it’s been incredibly long and nuanced dating checklists.

I like chivalry but with modern values. I want someone spiritual, but not religious, but definitely not atheist. I’ll date someone who’s divorced, but only if it’s been more than 2 years. I’ll date someone with a child, but only if they’re older than 13. I want someone someone good-looking that knows how to dress and cares about their appearance but not too vain. I want someone who travels a lot and has flexibility to travel but readily available for a date. I want someone who makes really good money, but has flexibility, and work is not their life. I want someone who’s fit and active, but doesn’t go to the gym every day. I want someone who cares about politics, but only a little bit, and I don’t want to talk about it all the time. I want someone with a dog, but not a small dog. I like brown hair, but not too light, and no freckles. They should enjoy a drink, but only once in a while, and never more than 2 at a time.

None of these things on their face are terrible statements. If you were just sharing some thoughts and feelings with a friend, or even with a new partner in a trusted space, it’s a start to a conversation. Many of these things are also likely to shift and change several times in a lifetime.

However, turning conversation starters into checklists is where we get into trouble, because as much as you might have all these nuanced thoughts and feelings about your perfect partner or how you imagine you want to live your life, the chances are slim to none that someone will arrive perfectly formed for you.

So, let’s take a look at what these checklists are doing and how we might transform them to be a bit more helpful.

Recipes for Disaster

Sometimes, daters say they “just want balance.” What I’m hearing is — I want balance, but in this very specific way that I’ve defined it. I’ve arrived at exactly who I am and done all the work I need to do. Now, someone just needs to come into my life and be my perfectly matching puzzle piece. Those who do not fit upon immediate inspection shall be banished to the undateable universe forever! Shazam!

That’s not balance — that’s a recipe. And it’s very subjective to your extraordinarily picky palate.

When you start calling out the exact recipe of human you desire with all the ingredient measurements, you’re playing a losing game of build-a-bear. No one can put together the person you want after submitting your order. That bear will come out burned every time.

It’s so tempting with those online profiles though, right? Maybe if you keep swiping, you’ll see the perfect recipe! Ding! The gingerbread bear is done, ready to be delivered. May I have a bite, please?

That’s a tall order. Or maybe in the case of your gingerbread bear — not tall enough, dang it! Send it back, try again.

The dating pool is full of real, complicated and flawed people (ahem, just like you) and even your perfect checklist on paper may somehow disappoint in person. You also can’t guarantee your checklist person is going to be into you! Holy cannoli, there’s another person involved in this whole thing too!

There is a give and take to our checklists that is very hard to see when we don’t know what’s in front of us. All we see is what we may lose, not what is possible to gain. Those checklist items are stubborn. We think we’d never be able to flex on some of them. And when we do flex, it’s not always a clear cut path to certainty.

Ahh, certainty. If only we knew on date one based on a perfect checklist. But relationships don’t really come to fruition like that, especially in the beginning.

Think of your dating checklist less like a baker and more like a stovetop chef using what’s available. It’s not an exact science — you can improvise, add a little of this and that, turn up or down the heat, potentially save the dish with an ingredient or two if you mess up, but keep testing the flavor to make sure it’s still okay. Our dates will likely need some adjusting, just like us, once we get all mixed together.

Or you can go hungry. Have it your way.

Blinded by the Checklist Light

Checklists also present a very tricky game that prevents us from seeing our own rigidities. There we are, shining our big bright flashlight on our date like a film noir detective but we get to stay in the dark, no secrets revealed, no introspection required. Ha! You only take one teaspoon of sugar and I take two, so I guess it won’t work. Goodbye! Next!

Little do you know, both of you might have been pretty happy with one and half teaspoons and a dash of cinnamon — a variation you’ve never tried — but you’ll just never know… such a shame.

Many times I hear these checklists coming directly from past experiences they’d rather not repeat, and so the person is “protecting” themselves from this experience in the future. In the case of an abusive partner, this is completely understandable. Hold that ground for sure. In the case of a small dog as a pet? Eh, slow down.

I know it’s incredibly hard not to create your own stereotypes from past experience. Your ex had a crazy mother, so you look out for someone who mentions their mom on the first date. Your ex had a gym obsession so you are wary of anyone excited about their upcoming workout. Your ex wanted you to come to church so you’re only comfortable with certain spiritual labels.

It’s natural to have reactions to things that are flags from your past, but when it goes too far, you won’t end up dating anyone because there will be overlap at some point with something you don’t like from your past. There just will. Our perfect partners are actually not perfect compared to our past, we just have enough we like about them to work things out this time.

Case in point — I’m a pretty clean and organized person. I like to fold and put away my laundry as soon as it’s dry (wrinkles, you guys, wrinkles!). I clean my bathroom floor corners regularly with a hand vacuum. I like all the dishes done before I go to bed. That’s me. I dated a few folks that were pretty disastrous in terms of cleaning and tidiness and when we broke up, I swore I would never be able to be with someone that was messy like that — ever. I associated that behavior with all the other things that didn’t work and lumped them all together.

Cue me, walking into my darling’s apartment for the first time, pretending not to be horrified, and thinking… it’s okay. We can work through this. And we did.

Why? Because of his ability to listen, care and compromise. That’s what I came to know over our first few weeks of dating. We are able to talk through just about anything, which makes addressing historical red flags much easier to do (thank you, therapy!). And thankfully, his dating profile wasn’t full of pictures of his kitchen floor because oh my god, crumbs invite critters people, get your sh*t together!

Now, it wouldn’t be fair if we didn’t address what some of his concerns might have been about me if he was sticking to the checklist. When we met, we lived an hour apart with very different schedules. I worked in production for film and television — a very intense, time-sucking and notoriously annoying job for partners. Film industry people are thought of as pretentious, name-dropping, self-centered a-holes by a lot of people. Hours are extremely unpredictable. Literally, it’s up to the filming gods when it’s time to go home 99% of the time. Plans get canceled, everyone gets exhausted and there is an overarching feeling for many on the outside of — why do you do this again?

Many folks on the apps in Los Angeles immediately swipe left on those in the industry, having had bad experiences about availability, obsession with work and getting deprioritized. Adding to that — I was in grad school and was having some serious health issues. It was… a lot. I was a mess. But we got through it.

Why? Because he was willing to give me the benefit of the doubt that I was invested, even if I couldn’t always show it right then. He hung in there to ride out the storm and saw that one of my core values is follow-through. Our connection, our laughs and our communication filled in the gaps until life was in a better place for us to move forward in a bigger way.

Also, did I mention — he wasn’t fully divorced on paper yet? And we weren’t on the same page about having kids? And we are the exact same height? And I’m a day older? And we are both youngest children? And I was making more money than him at the time?

Trust me on this because I practice what I preach. Get rid of your harsh checklists. Throw them out the friggin’ window.

Had we both sat in front of our phones and ruminated on what we didn’t like about each other based on our past and where we didn’t check off each other’s ideal lists, we could have easily convinced ourselves it would never work. Thank goodness we didn’t. Our biggest problem now is that I don’t say I love you often enough. I ask him to vacuum instead (which he does).

Stay tuned for Part 2: Feelings Over Facts — Checklists That Elevate your Dating Life

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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.