Want to find love? Make a list!

By Caitlin Kelly

If you’re still hoping to find a partner, it can feel like an exhausting and overwhelming search.

I spent my 20s dating a lot of men, but not wanting a long-term commitment from anyone, certainly not marriage. I didn’t want children and I wanted, long-term, to get to New York, a difficult thing for most Canadians.

So after I moved to Montreal, I fell in love with an American medical student from New Jersey. I was able to obtain a “green card” allowing me to live and work permanently in the U.S.

We spent seven years together, but should never have married.

I liked this piece in The New York Times’ Modern Love column:

I experienced repeated collisions of misaligned values and discovered personality traits I wanted to avoid. Dates that caused me to be versions of myself I didn’t like and cost me time that I could have spent on my couch: just me, a Vicodin and a book about sadness.

To break this cycle, I decided to track it all. Make sense of the patterns and change them.

Cue the Trello board. As of today, the board has six stages and eight traits. It’s similar to the business development process of a salesperson, with each stage representing a step toward a successful deal and each trait representing a characteristic that is more likely to lead to success.

The stages are: To Vet, Vetting, Vetted, Scheduling, Scheduled and Dating. Each person is represented by a Trello card — a kind of digital sticky note.

Before I go on a date with anyone, his card progresses from left to right, passing through these stages until we’re dating. If we never get that far, I archive his card, in which case an archived card is all he will ever be.

I evaluate my potential dates based on eight traits. Five of those traits I try to learn about before the date. The remaining three I think about after the date.

Before the first date, I try to determine the following: Does he make me laugh via text? Does he live in L.A.? Does he like his job? Is he down to go backpacking? Will he get on the phone?

Years ago, after my miserable two-year marriage — he walked out barely two years to the date of our marriage, and remarried a colleague within the year — I found the acronym PEPSI, and used it think more seriously about compatibility with potential partners.

I stayed divorced and single for six years.

I had a few marriage proposals, one very serious.

But I didn’t want them, from those people, one from a man I had had a huge crush on in my 20s after I profiled him for a Toronto magazine. Oddly, later, we dated seriously for about six months, but there was a large age difference — that didn’t bother me at 24 but did at 39.

I did want to re-marry, even though my first husband was unfaithful, which broke my heart.

I have spent a lot of my life alone and, while I’m pretty independent, I much prefer having someone loyal and loving to share my life with.

I knew a few women like me who kept striking out and finally made a list of what they most wanted in a partner.

Everyone thinks: cute, smart, rich.

After a few decades in the trenches it’s a lot more like: funny, smart, kind, flexible, accomplished.

I wanted a unicorn — someone virtually impossible to find in New York City — a man who was both highly accomplished but also modest about it.

Someone able to be deeply serious and responsible about the matters of adult life (bills, savings, health issues) but able to laugh a lot.

Someone generous emotionally, able to easily express affection, something I struggle with.

I found Jose online while writing about online dating for a women’s magazine.

We would never have met otherwise — even though we had people who knew us both.

This was then part of my thinking if I met a man who seemed interesting.

So, how compatible, really, were we?

Hence PEPSI:

P for Professional

E for Emotional

P for Physical Attraction

S for Spiritual

I for Intellectual

There were some serious doubts on both parts.

P met the bill, both of them.

E…well, two very stubborn people!

He felt I wasn’t nearly spiritual enough for him, a devout Buddhist. I told him that seemed mighty judgmental.

I feared he wasn’t intellectual enough.

Yet here are, 21 years later!

Some of the qualities I think essential in a life partner include a phenomenal work ethic, a spirit of generosity for himself and others, awareness of the world and how it works (and doesn’t), a commitment to making others happier.

Resilience is huge. We’ve been through a lot of stuff — deep family conflicts, his turning full-time freelance, his diabetes diagnosis, my breast cancer. I wanted someone with a spine and a heart!

We each arrive to the quest with our own specific deficits and needs, our strengths and weaknesses.

But knowing who we are and what we value most is a good start.

Commitment is key.

16 thoughts on “Want to find love? Make a list!

  1. Except for the S, my list was the same as yours. We met online as well, but quite by accident as we weren’t matched (don’t know why). I saw that he had trained as a sommelier and so had I; I thought there were some wine conversations to be had. A week later we phoned, a month later we met face-to-face, two years later we got married. He is the love of my life. It is such a gift when you make a real connection that is like putting a key in a lock. 🙂

  2. Jan Jasper

    As we get older we should be better able to articulate our gotta-haves vs. our nice-to-have traits. Dating someone because your first date is fun and there’s physical chemistry is silly, once you’re of a certain age. – there has to be more there. The challenge is, knowing what really matters? I’d have thought “he can make me laugh” is essential, but I had a long, wonderful relationship with a man who rarely made me laugh.
    As for dating sites, I’ve had too much experience studying them, and it seems they cannot quantify some of the most important traits. Even if Lynette used a dating site that offered a check box for “sommelier,” that doesn’t mean you two would have been compatible in all the other ways.
    Some sites – like eHarmony – claim to match you with people of a compatible temperament. I quit eHarmony after being matched with too many Born Again Christians and 2nd Amendment rights nut jobs. In my profile I had stated that I was an Atheist, and politically progressive, but that didn’t register with eHarmony’s algorhythm.
    Dating sites rarely give you any way to emphasize, for example, that you’re an intellectual looking for another intellectual On Match, for example, on their list of leisure activities I could check “Book clubs” – but that’s mostly for best sellers, and smart people I know generally aren’t big book club attendees.
    Match can screen for people who agree with you on religion, wanting kids or not, smoking, drinking, cannabis friendly, etc. But that just scratches the surface.
    Caitlin’s key valued traits – emotional generosity, etc – cannot be measured by a dating site.
    And bear in mind that if a member of Match or OK Cupid or Plenty of Fish finds a partner, they lose a customer. Maybe that’s part of why their AI doesn’t seem to try that hard to provide meaningful “matches.”
    I had a wonderful two and a half year relationship with a man from OK Cupid who was only a 79% match. He’s the guy who rarely made me laugh. Yet I routinely get “matches” in the 80-90% with men with whom I clearly have little to almost nothing in common.
    Back to Caitlin’s original point, yes, having a checklist is good – the first step is knowing what you value.
    Then the hard part is finding that person.

    1. Absolutely!

      There was no legitimate way for me to say — “accomplished but modest” because those are such subjective words! So is “generous”…Jose, even as a new boyfriend, knowing how strapped I was then for cash, bought me a toaster and a colander and two air conditioners…I was so stunned by his kindness but also his practicality. I REALLY needed not to swelter every summer and I did.

      We also would never have matched as our interests differ quite a bit (he LOVES golf, I like it) but our essential values match up very well.

      We know we are very lucky — but have also worked hard to smooth over the rough times.

      I dated a lot of guys in the six years after my divorce and had a very good time with a few of them. But none were husband material. That’s a totally different bar to clear.

    2. I agree that it’s difficult for those dating sites to quantify the important traits. The funny thing was that our profile basics were quite similar, so theoretically we should have been matched for each other, but we weren’t. I happened to stumble across him, as it were – a lucky happenstance. We figured out the important stuff about each other (other than wine knowledge!) over time, and that’s really the only way that can happen.

  3. Jan Jasper

    If your profile basics were quite similar, then yes, even at the simplistic level that the algorithms work, you 2 should have matched. So great that you found each other! Cynics would say this is the dating sites wanting to make sure you don’t find someone, so you will pay to renew your membership.
    Kind of like me being matched with a Trump supporter because we both like dogs. That said, dating sites are still the best way. An older woman like me doesn’t meet that many single men by chance.

    1. Thank you!

      I got matched with a couple of people who were completely incompatible, as well – just totally incomprehensible. There may be something to them trying to keep you on as a subscriber, as you mention.

    2. It’s difficult — finding someone you like and respect shouldn’t feel like such a chore, but it is. I enjoyed my post-divorce boyfriends and one broke my heart (I met 2 of them crewing on sailboats and one I knew years before) but didn’t want to marry any of them.

  4. Emotionally generous…yes. That’s an important part of what I look for in a partner too. I hadn’t heard of the PEPSI acronym before! I’ll have to try it out when I’m next dating (the pandemic has put a stop to that for now). I was in a relationship for a while with a lovely man who I met online, but we didn’t click intellectually and that was a real barrier. I’ve got to the stage where I’m looking for long-term commitment, but it isn’t always easy to find.

    1. It seems silly, but it’s a useful reminder…plus your list!

      The intellectual piece is really important to me. Jose is not classically intellectual but reads smart stuff and is someone I turn to daily for ideas and feedback on my work….as he is also a fellow journalist. That partnership has proven to be terrific for both of us.

  5. Jan Jasper

    Caitlin, I would guess that you and Jose both being in journalism is a big part of why you never run out of things to talk about. A classic intellectual person can be quite dry, and I think we’ve all met people with postgraduate degrees who lack curiosity about the world – even though they are clearly not stupid. I really need someone who is smart and interested in ideas and enjoys reading and talking about these things with others.

    1. True!

      Our standard line is “off the record!” when we share stuff we can’t yet make public that we’re working on…good grave marker, too.

      You just can’t be a successful journalist without insatiable curiosity and openness to new experiences.

      I used to wonder if a professor would fit the bill for me, but no. We have 2 on our apt. floor and I wouldn’t ever have found either attractive, no matter how. smart. I am not a fan of a lot of academia. I never went to grad school. I didn’t enjoy much of university although I love to learn new things.

  6. Jan Jasper

    That Jose got you the air conditioners and other things you needed rather than something traditional and useless like flowers, told you a lot about him. I remember a guy decades ago who wanted to date me and I had some things that needed done in my apartment, not heavy work but things I could have used help with, tasks that required a second person. All he wanted to do was take me to dinner or bring flowers. I was not impressed at all.

    1. He initially brought me bread!

      One day I lost it and said “Come fix my printer!” He got it, and did.

      I buy my own flowers, and happy to do so.

      My own father was great at fancy stuff but not practical stuff. So I really value practical stuff BUT Jose (bless him) has also bought me many pairs of beautiful earrings.

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