dating is not a CRM

disclaimer:** i’m stuck on a long flight and taking a break from work, so i started writing this mostly off the cuff. it became more personal than i intended… but here we are.

i have recently accepted that i cannot date more than one woman at a time. honestly, even two feels administratively irresponsible.

the problem is that modern dating almost requires you to talk to several people at once, because the truth is that most of the time, none of them will turn out to be right for you.

sometimes someone up and disappears – or reschedules indefinitely. sometimes the attraction is just not there (me to her, her to me, both to each other). sometimes our personalities or lives simply do not fit together. increasingly, i meet women who either do not want children or might want them at some vague point in the future, while i have wanted to start a family (with the right woman) for at least a decade and a half.

nobody has necessarily done anything wrong. these women are often perfectly nice, interesting, attractive human beings.

they were just not the person i am looking for.

so then i go back to the start, opening the apps again, engineering scenarios for chance encounters, accepting setups, and eventually meeting another handful of perfectly lovely people whom i do not want to marry.

after enough trips through that cycle, i decided to try dating the modern way: keep several conversations and dates going at once and assume most of them would go nowhere.

i was dating five women. and because i genuinely wanted to remember what each person had told me, i created a spreadsheet.

yes. a spreadsheet.

names. jobs. siblings. upcoming trips. dog names. important stories. whether she hated cilantro or loved it. potential red flags, absolute green flags. if she had cats. 

i had accidentally turned my dating life into a sales pipeline.

and the thing is, i was not doing it because i did not care. i was doing it because i did care.

i did not want someone to tell me about a stressful situation with her sister and then, three days later, have me ask, “so do you have any siblings?” no matter how lovingly maintained the spreadsheet was, it still reduced actual human beings into rows.

woman 3: likes italy. close with grandmother. follow up regarding work presentation.

that is kinda insane.

and to be clear, i have always kept notes when i am very serious about someone. friends’ names, favorite things, phrases that unlock entire stories like “titty pong” or “east meadow mall,” and random details i do not want to forget.

i want to understand her world and remember the people and things that matter to her. that feels very different from opening excel before a third date to confirm which woman recently went to nashville.

some friends have told me i need to stop caring so much. be more casual. keep my options open. treat the whole thing more nonchalantly.

but unfortunately, i am a chalant person.

deeply chalant.

perhaps debilitatingly chalant.

when someone tells me something, i remember it. when i finally like someone, i want to know what is happening in her life. i want to remember her friends’ names. i want to ask how the thing she was nervous about went. i want to understand the references that make no sense to anyone else.

i do not know how to manufacture the exact amount of emotional unavailability required to appear appropriately unbothered in 2026.

dating, especially over the last couple years, has drifted so far from what i ever imagined it would be.

i thought dating meant meeting someone, deciding you liked each other, and then spending more time together to see where it went.

apparently it now means maintaining several lightly engaged conversations, waiting six hours before answering a text you saw immediately, pretending you are not excited, and never acknowledging that you would actually like to see the person again until both parties have independently retained legal counsel.

everyone is supposed to be interested, but not too interested. available, but never immediately. intentional, but somehow also “just seeing what happens.”

you are expected to date five people at once while acting as though none of them have any effect on you whatsoever.

i tried that. i hated it.

i had the spreadsheet. i hated it.

logistically, i understand it. when genuine compatibility is rare and people can disappear at any moment, focusing on one person can mean spending three weeks getting to know someone who suddenly evaporates because mercury retrograde convinced her attachment style that the vibes have changed.

emotionally, it makes no sense to me. i do not want a roster. i do not want a funnel. i do not want quarterly romantic performance metrics.

and honestly, i do not love the idea of being on someone else’s roster either. this is not a double standard. i do not want five women in rotation, and i do not want to be one of five men waiting for my turn at bat.

i understand that nobody owes anyone exclusivity after one date. but there is something increasingly gross to me about two people trying to decide whether they genuinely like each other while both are quietly maintaining a full bench.

i do not want a roster.

i do not want to be on a roster.

i want two people paying attention long enough to find out whether there is actually something there.

i do not want to become better at caring less. i do not want to train myself to see people as interchangeable just because that would make dating more efficient.

i want to pay attention to one person. i want to remember what she said because i was actually listening, not because cell g14 says her dog’s name is ‘anthony.’

i am not nonchalant.

i am chalant.

so for me, dating is binary.

one or zero.

after meeting so many women over the last year and a half or two, i have spent the last few weeks at zero.

not because i could not find another date. i just needed a break.

eventually, i will go back to one.

but i am never going back to five.

(the nerd in me really wanted to write 101.)