When Dating Feels Like A Game Of Where's Waldo, This Hack Helps

Applying the practice of intentional spending to find my Waldo in a sea of mismatches.


“I’m too busy to date” is easy to say because it’s true. And also because, historically, while I’ve been pretty good at relationships (until I’m not), my approach to dating could use some work. It’s a respectable cop out with just enough truth behind it.

Since moving to Los Angeles in September of last year, dating hasn’t been a priority for me. I’ve given precedence to laying the foundational pieces for life in a new city: finding the right assortment of rugs, becoming a plant person, discovering my love of hand roll bars and getting to know my new people well. I’ve made room to date casually in the midst of falling head over heels in like with my new home, but romance isn't top of mind; generally, I think, because it’s out of sight.

When living in New York, relationship envy is inevitable. I was boyfriend-dating, not because I wanted a relationship (or knew what type of relationship I needed), but because I was painfully aware of what I didn’t have. I passed far too many finger-laced couples on Tompkins Ave, and internalized my lack as a flaw. The car-to-destination culture of LA means I see relationships less; meaning I want a relationship less. My main subject of envy these days is not a boyfriend—it’s a sport utility vehicle with cooled seat functionality.

That said, every few weeks, I do remember that I’ve been single-ish for two+ years. That “ish” is a footnote for the three (of the tragically, dozens) romantic situations I’ve endured since my last real boyfriend - a fast-tracked pandemic love that taught me how important it is to show up unabashedly as yourself early.

Those three situations that followed, which I affectionately call my unholy trinity, include my first real LA crush, the one who forgot to let me know he had a boyfriend (2022); my older French man, the one whose West Hollywood penthouse wasn’t enough to excuse the age gap, said a good friend (2023); and my bi-coastal fling with a Brooklyn-based Lawyer, the one who told me how important it was for him to be in a relationship with a Black man, to then move on with someone who’s not (2023)—we’re still sore from that one, chile. If I were to line the three of them up, there’d be no discernible qualities in common, apart from their failure to materialize into something significant long term.

“Sifting through duds hasn’t been an issue for me until recently. I never minded wasting time on lukewarm third dates. But today, I’m too busy to aimlessly date my way towards Waldo. So, what now?”

I have wondered in the past why my dating history is so varied. I have friends who’ve dated versions of the same person until they finally settled on one. While that may be in issue in itself, there is something to be admired about their consistency, and the focus that level of consistency demands. My dating history looks more like a Where’s Waldo map, with I don’t know how many guys over the years concealing the one (I hope) there is to find. Sifting through duds hasn’t been an issue for me until recently. I never minded wasting time on lukewarm third dates. But today, I’m too busy to aimlessly date my way towards Waldo. So, what now?

Just a few months ago, my great-friend-turned-roommate Theresa — who is also on a single and too busy to date aimlessly journey — and I set a Kardashian-inspired intention: introduce more intentionality into our dating lives. As depicted in Season 3 of The Kardashians, newly single Kim made a list of all the qualities and attributes she’s looking for in a man, post-Pete. The list was her version of manifestation, and it reminded me of how I shifted my approach to shopping this year. In years past, I was a pretty aimless shopper. See-it-want-it-buy-it was my approach. But this year, after chatting with my very well-dressed friend Kayla, I challenged myself to adopt her shopping challenge: limiting my purchases to twelve apparel things (with some success; right now I’m at sixteen).

These limits for clothing, accessory and shoe spending have encouraged me to hone in on my personal style, developing a strong image for how I want to show up in the world, and shop accordingly. I’ve passed on countless items I liked, but couldn’t justify as one of twelve. I’m still mourning the one-of-one laced Bode shirt; so gorgeous, but not 100% right. Every purchase I’ve made this year has felt like an intentional expansion of my wardrobe, and I’m loving how focused I’ve been. So much so, I couldn’t help but wonder: Is there an application for dating?

“It’s helpful to have a guide, so I don’t leave the vintage store with a leather bomber jacket when I was really looking for a lambswool cardigan. Or, so it’s easier for me to identify Waldo. ”

Theresa and I created our own KK Dating Lists to be just as intentional with who we go out with. Mine includes sixteen items—a range of characteristics (like #14: shy, but not shy with me), physical attributes (#2: porn stache as a secondary, but semi-regular facial hair style), specific scenarios and feelings (#4: would be friends with my Aunt Lisa). No man, I’m sure, will meet all sixteen—and some of these items could only be revealed over time—but it’s helpful to have a guide, so I don’t leave the vintage store with a leather bomber jacket when I was really looking for a lambswool cardigan. Or, so it’s easier for me to identify Waldo.

At the same time, I’ve realized I need to get real about how Waldo should make me feel. Quick note: I promise I will limit the Sex and the City references within my dating writing, but it wouldn’t be my humble return to this subject matter without one. This needs to be said:

When Carrie Bradshaw ended things with the Russian in the SATC series finale, An American Girl in Paris (Part Deux), Sarah Jessica Parker poignantly delivered the line that ruined me: I am looking for real love; ridiculous, inconvenient, consuming, can’t live without each other love. Sure, but the thing is - those are not positive adjectives. And still, they became the filter by which I evaluated my feelings for many guys over the years.

Late last year, I reflected on a crush from 2021 who made me “fall over from nausea at the very thought of him” - that is incredibly ridiculous, inconvenient and consuming. It’s also incredibly toxic. Carrie, the hero of my New York 20s, who thousands have modeled their dating lives after (consciously or not), set me up to find fault in men who were good, but normal; good, but safe. After a summer of having fun with many obviously, yet deliciously wrong men, this next phase of dating for me is about avenging justice for the good guy. I’ve added a lucky number seventeen to my KK list: is a genuinely good guy.

At risk of being painfully earnest (as if “good guy” wasn’t enough), I think love is worth being deliberate for. I am busier today than I’ve ever been, settling into LA life, while running back to NYC every chance I get; thriving in my full-time work, while pursuing too many side-ambitions; and finalizing the third and final self-edit of my novel. Despite that, I would gladly make time for someone that makes sense. But they have to make sense. “I’m too busy” is less of a cop out, more of an acknowledgement of the value my time, energy and ambitions hold - enough to prioritize them over every guy I triple-take on the weekend. If there’s a hack to dating, perhaps it’s this: Window shop with purpose, try on if it feels right, and purchase if you can’t imagine going home without it.

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