Use that Checklist as a Guide, not a Rulebook

Except for those among us who are freshly single after years off-market (and still orienting themselves to their new context), most of us singles have a sense of what we’re looking for and attracted to in a romantic partner. The longer we’re single and oriented to this gig, and the older we are and have a strongly developed sense of ourselves, the more we tend to settle into a sense of the kind of romantic partner we want and who suits us.

This sense of what we seek in a romantic partner often takes the form of a mental checklist of qualities, characteristics, desirables, and/or must-haves. While such a checklist can be a helpful guide, keeping us from expending too much time on poor matches, if a checklist is too rigid, it may prevent us from meeting our ultimate goal of relationship and right romantic partnership.

The Role of a Checklist

The purpose of a checklist should be to help you find a suitable romantic partner, not rule good potential partners out. To that end, be careful how you use your checklist so that you don’t prematurely dismiss a great connection.

The abundance of profiles that come with online dating can amplify the propensity to be dismissive of potentially good matches. It’s okay to be picky, but if you truly seek relationship, at some point you need to pick someone rather than succumb to the paradox of choice. And with luck, they’ll pick you too.

So, how to use a checklist productively? Let’s explore…

Re-Purposing that Checklist as a Guide

Think of your checklist as a GPS, steering and navigating you to where you want to go, in this case, to a romantic partner. The purpose of GPS is to help you arrive at your destination. When you plug in your destination, sometimes GPS gives you alternate routes to choose from. But those aren’t the only routes to your destination, GPS is simply trying to find your best options. Sometimes, I go off-route and GPS has to catch up to me and reconfigure my route. And sometimes I do that romantically as well.

Furthermore, there are plenty of destinations worth visiting, not just one. So, why be rigid about one route to one destination? Let’s expand our navigation options, so we can find a suitable destination rather than limiting ourselves from the get-go.

Breaking Down the Checklist

The checklist is to help you discern good candidates for relationship, but if you give equal weight to all items on the checklist, it works more as a rulebook, a binary yes/no in/out scenario, potentially dismissing good possible mates because they don’t fully measure up to a perceived ideal. But Ideal isn’t real, and holding out for it is a pointless endeavor. Reality is where we live. To keep it real, look for the real person whose preciousness you can appreciate, despite their imperfections.

To re-envision your checklist as a guidance system, you need to breakdown the items in your checklist. Consider each item a guidepost to help you get where you are going, and keep in mind that some signage is more important than other signage.

Must-Haves vs. Preferences

Consider the qualities you find attractive in a partner–physical looks, personality traits, values, education level, politics, faith, career, sexuality, location, etc. What are you drawn to in a partner? What do you want? What do you need? What turns you on?

Must-Haves

Now, breakdown those qualities into must-haves and preferences. Must-haves are the qualities that without them are dealbreakers. These are qualities that are so important that you can’t envision relationship without them. The nature of these qualities has different weight for different people. You get to decide what your must-haves are.

While it’s important to define what you must have in a relationship/romantic partner, try to keep your list of must-haves small. The longer and more rigid this list becomes, the more narrow your pool of possibilities and potential matches becomes in turn.

Preferences

Preferences are those qualities that are inclinations, turn-ons, and desirables. Knowing your preferences can help you identify good potential matches, and by not qualifying them as must-haves, you allow wiggle room for flexibility, the wonderment of the individual, the person who surprises you, and the exciting expansiveness of possibility.

For Example

In my years as a single, I’ve discovered that I have a strong inclination toward men of Mediterranean descent. I’ve dated a ridiculous amount of men who claim a Jewish, Italian, or Greek heritage. That’s a preference but not a must-have.

However, physical attraction is a must-have for me. If I don’t feel physically attracted to a man, then I don’t see the point of exploring the connection. It just so happens that I find a lot of men of Mediterranean descent particularly physically attractive, but Mediterranean heritage doesn’t account for all of the men who I find physically attractive.

A friend of mine has a very particular sexual proclivity. For him, this is a must-have in relationship. It’s a very specific and strong inclination that’s important to him. This proclivity narrows down his pool of potential mates dramatically, but it’s important enough to him that he opts for that.

Different qualities have different importance for different people. For some, religious faith is an important must-have in a partner. But if that must-have takes the form of a specific denomination, that narrows someone’s options significantly, rather than allowing some wiggle room in what form that faith can take. As you think about your must-haves, consider where you can allow for that wiggle room.

You

You get to decide what your must-haves and your preferences are. Knowing both can help you discern good potential romantic connections, and limiting your must-have list will help keep your possibilities open. The more you limit your must-haves, the more you open yourself to possibilities. Conversely, the longer and more specific your list of must-haves, the narrower your pool of possibilities becomes.

Turn-Offs vs. Dealbreakers

Much as must-haves and preferences can help you discern a good potential romantic partner, turn-offs and dealbreakers can help you avoid wasting overmuch time on individuals who aren’t a good fit. To return to the GPS analogy, turn-offs and dealbreakers help you navigate away from dead-end roads and avoid plugging in a destination that’s not where you really want to go.

Turn-Offs

A turn-off is anything that is an undesirable or less than ideal quality, but not necessarily a dealbreaker. Pay attention to turn-offs, they rightly give you cause to pause, but if the person has enough attractive qualities, consider whether the connection is worth further discernment. After all, we’re all imperfect. In the larger context of the individual, is the turn-off potentially negotiable for you?

Dealbreakers

A dealbreaker is a quality that you feel so strongly about that you can’t even entertain the idea of relationship with someone because of it; it’s an absolute with no room for negotiation. As with must-haves, the longer the list of dealbreakers, the more your pool of possibilities narrows.

For Example

Damon was a smoker. A turn-off for me, but I liked Damon more than I disliked his smoking. Ideally, I’m not looking to get involved with a smoker, but I made an allowance for him because I really liked him.

Paolo has multiple marriages and divorces in his past. I’m a divorcee myself, but multiple marriages/divorces always gives me pause. That said, he has many qualities that outshine this aspect of his history. And we all have histories. His history is part of him, but it doesn’t define him. With Paolo, I choose to look beyond the history and see the man he is now.

I was enjoying getting to know Jay, but when he disclosed that he’d be celebrating the Christmas holiday with his ex, that was a dealbreaker for me. At this point in my life, I won’t get involved with a man who can’t leave his past in the rearview mirror. Been there; done that; can’t do it again. That situation was an emotionally turbulent experience that I don’t care to revisit.

You

When defining your dealbreakers vs. turn-offs, consider which are absolute non-negotiables and where you can allow wiggle room for the right person. What are your limits and where can you be flexible? We’re all imperfect; what imperfections can you allow for? As with must-haves, the longer the list of dealbreakers, the more your pool of possibilities narrows.

A Spectrum vs. a Binary Perspective

As you sort through your must-haves vs. preferences and turn-offs vs. dealbreakers, envision it as a spectrum. At one end of the spectrum is the must-haves and at the other end, the dealbreakers. If one is white and the other black, everything in between is a gradation, mostly gray.

This is where we live, the messy gray. Life isn’t a clear-cut simplistic binary endeavor. Life’s complicated, and so are people. Where on that spectrum are you going to draw your limits? How broad are you going to keep your spectrum of possibilities?

Seeing the Person Behind the Profile

Behind each profile is a real person. Okay, except for the bots and fake profiles which are an unfortunate annoyance with online dating…but for the most part, the profiles represent real people, individuals with stories, histories, successes, and failures.

Profiles are a watered down version of the real person. Some people have nothing to say in their profiles–they literally (I’m an English major–I’m using that word correctly.) don’t write anything in their profile. Such profiles don’t promise much for the person behind them. But, when you find someone whose profile resonates with you, explore that.

Embrace exploring the nuances and substance behind the photos and bio blurb. Try to keep any flaws, imperfections, and turn-offs in perspective as you discern the person and your connection (as long as they hit your must-haves and you don’t encounter any dealbreakers). Allow for the preciousness of connection, when you feel it.

That checklist we each have serves us best as a guide, not as a rigid prescribed route. Have fun exploring off-road, and be mindful of recognizing the person who you want to lock in as your destination despite what may or may not be on your checklist.

Here’s a paragraph from my Match profile that goes to this:

I am looking for someone that I have a genuine connection with, who is sincerely looking for a someone special in their life. Someone who, if we are lucky enough to find each other, is willing to look up from his checklist (if we are connected the things on the checklist stop mattering) and see me looking back at him, and who is willing to follow it and take a risk, despite our mutual imperfections.

Final Thoughts

You get to decide what you need and what your limits are in a romantic partner and relationship. As you determine those needs and limits, consider where you’re able to be flexible and allow room for the nuances of the individual. The broader your spectrum of possibility, the more likely you are to find someone.

Good luck navigating to your destination!

Up Next: Discerning Who You’re Looking For

Why Not?

In the spirit of my dear friend Erik, who this year has embraced “Why Not?” in his life, I repost this. In this past post, he considers whether or not to purchase a cap. This year, he’s levelled up living with a Why-Not attitude. Good luck to him, and may you find the spirit of “Why Not?” in your life as well…

I’ve been primarily dating long-distance for over a decade. For some men, dating long distance is a non-issue; for others, it’s a deal-breaker; and some men, intrigued by me, take it under consideration, not having considered it before. Because the reactions to dating long distance are so wide-ranging, I generally ask the men I interact with–Why are you willing to consider a girl from Nebraska?

Recently, Pierre responded, “Why not?” Almost a decade ago, Stanley answered the question the same way. I love that answer. Why not?

Why-not is an empowering and expansive stance for considering not just long-distance, not just dating, but life.

The why-not of dating long distance has expanded my life and brought me memories and men who I treasure as part of my story, even in the past tense–dancing in an open-air blues bar in Memphis with Damon; theatre-binging in Chicago with David S; riding around Santa Fe on the back of David M’s Vespa; drinking wine, watching the sunset, and stargazing on Edward’s rooftop terrace in Old Town Chicago; exploring the Lower East Side with John.

Embracing Why-Not

Why-not is the difference between doing something and thinking about doing something. Starting with why-not rather than why has led me to some compelling life experiences. For example…

Paris

I wanted to go to Paris. So, why not? I went alone, but I went.

Photo: Me with my Parisian boyfriend in 2013. Okay, he was really a street performer, but what fun!

Aerial Silks

Marvelling at the aerialists in one of the shows I went to with David S., I whispered several times, “I want to do that, I want to do that….” A few years later, I finally asked myself, “Why not?” and found an aerial silks studio nearby.

The Slice Literary Writers’ Conference

Seeing that Slice Magazine (now defunct) was hosting a Literary Writers’ Conference, I thought, “Why not submit an essay to see if I can attend?” I was accepted! Tentative that I might be out of my element, it turned out that I found myself in a sea of fellow English majors–I fit right in!

One of the conference keynotes at the conference was Nicole Krauss, my favorite contemporary novelist, so…Why not go up and talk to her after lunch? While I was talking and gesturing, she surprised me by taking my hand! It’s the only time in my life when I really didn’t want to wash my hand after shaking someone else’s. (There was some regret and hesitation when I did wash my hands later, but I do like to practice good hygiene, especially after using the toilet.)

Pandemic Playlist Porch Concerts

During the early days of the pandemic, I saw the videos of Italians serenading each other from their balconies and Spaniards applauding healthcare work workers at 8 p.m. I thought, “I can do that,” so Why not?

For over a year, I curated a pandemic playlist, posting a song of the day on social media and going out on my porch at 8 p.m. to play it via Bluetooth (Admittedly, I’m no musician–my serenading took the form of playing DJ.). Sometimes neighbors came to listen and socialize (at a safe distance and outside). I grew a small social media following, and I was interviewed for two different radio stories. I did one thing and other things happened.

Photo: June 2020. I’m in the foreground, with friends and neighbors who came for a Pandemic Playlist Porch Concert in the background.

Why-Not is an Openness to Exploring Possibilities

Not every why-not will end in success. But starting from a place of why-not rather than a place of why is starting from a place of possibility rather than a place of limitations. It’s starting without a box rather than in a box. Even why-nots that don’t fully manifest can better you, stretch you, and build your confidence and willingness to put yourself out there until a why-not does fully manifest.

Why-not is about trying to make things happen, but sometimes things don’t. Here’s a mix of why-nots that have and haven’t happened for me…

Writing

When I started writing in earnest, several friends commented that I should write a book. Hmmm….Why not? I asked myself. A decade later, I have an extant manuscript that remains unpublished and continues to require revision, but I WROTE A MANUSCRIPT. There are plenty of writers out there and plenty of manuscripts, but there are also plenty of people who dream of being a writer and never write a manuscript.

My manuscript itself is a mixed success, but it’s something I did, and the manuscript has set me up for other why-nots–a revised chapter of that manuscript got me into the SLICE Literary Writers’ Conference and another revised chapter won third place (and $250!) in the memoir/personal essay category of the Writer’s Digest 88th Annual Writing Competition.

Blog

Why not start a blog? Check. But, as some of you know, this is a second go-round. My first attempt was a less focused, and thus, less successful attempt. Last spring I asked myself–Why not give it new life and energy? We’ll see where this why-not takes me.

TED Talk

Why not pitch a TED Talk based on one of my chapters? I did, unsuccessfully. You can’t know which why-nots will fully manifest and which won’t, but you won’t find by out thinking about it, you can only find out by doing something about it.

Accomplished Writers

Why not pitch myself and my story to Leonard Pitts Jr. and Bruce Feiler? Leonard Pitts Jr.’s assistant contacted me, but in the end nothing manifested.

Bruce Feiler’s assistant also contacted me, then he went on to set up a Skype call for me with Bruce (in 2018 before Zoom’s pandemic heydey). Bruce interviewed me for his Top 10 New York Times Bestseller Life is in the Transitions. I’m on page 236.

Inviting the Why-Not (or Not)

Sometimes why-nots happen and sometimes they don’t. Why-not is starting from a place of possibility, discovery, and action. Why-not is active and assertive versus the passive inaction of why. You can only find the answer to possibility by pursuing the why-not. As my friend Bob said in the radio story about me, “She’s always up to something.” It’s because I’ve learned to start from a place of why-not–How else am I going to make things happen in my life?

Why-not is the boundless “Yes” of Yoko Ono. Perhaps you know the story of how John Lennon and Yoko Ono met when he came to see her show before its official gallery opening. In order to view one of her pieces, Lennon had to climb a ladder and use a magnifying glass to read the small-type text of “yes” on a canvas. Yes–a word of possibility that gobsmacked John Lennon.

Yes and why-not are invitations to possibility. What and who are you overlooking inviting into your life? Why not open yourself to yes and possibility? Why-not invites you to transform the dream into reality–dream it, research it, enact it.

Why-not removes the barriers that why embodies. Why not go to Paris alone got me to Paris. Why go to Paris alone would have kept me thinking about it or dismissing the idea altogether.

Why not doesn’t have to be a high stakes question, it’s just a question that opens you up to possibility rather than starting from a place of having to rationalize something. The other day, my friend Erik asked me whether he should get a Scally cap, not sure if he could pull off the look. My answer, naturally, was–Why not?

Of course, Erik getting a Scally cap is a low-risk scenario. Sometimes there are good reasons to answer why-not rather than leave it unanswered. I can think of plenty of good reasons why not to jump out of a perfectly good airplane, for instance.

Money, time, risk, and your feelings can all be sound answers to why-not. As someone who opens herself to possibility by dating long distance, I take a lot of precautions to minimize risk while still opening myself to possibility. I don’t go on a long distance date with just any man. The point of dating long distance is to find a special connection and with that, some fun. It’s not about having a reckless and wild adventure. To that end, I carefully gather information and discern both the man and the connection before committing to a long distance rendezvous.

I invite you to practice applying Why-not in your life. Why not take that trip? Why not apply for that job or start that business? Why not hike the Appalachian trail (Maybe I’ll do a portion in 2025…but first I have to plan my why-not trip to Italy in 2024!)? Why not climb Mt. Kilimanjaro (My friend Anne did for the first time at the age of 65, and she’s done it a second time since!)?

As for dating, Why not make a dating profile? Why not ask someone out if you’re interested in them? Why not consider someone long distance if you really like them? You know your whys better than I do, I simply challenge you to turn your whys into why-nots. Sometimes you’ll have a good reason not to do something, but maybe you’ll also find some room for possibility and making things happen. Who knows where a why-not could take you? Aren’t you curious to find out?

Final Thoughts

Who and what are you going to invite into your life this year? Pursue your possibilities and good luck why-notting out there!