Dating has become incredibly complex. Whereas people used to seek adventure and enlightenment when meeting other humans, now they’re looking for red flags. And there’s no shortage of them.
Can you spell A-V-O-I-D-A-N-T?
When you enter into a movie theater you submit to a tacit agreement to “suspend disbelief.” This is what you need to do on dates too.
Because here’s what’s going on under the hood: when we meet a new human, subconsciously we test to see if they’re a member of our tribe, if they’re trustworthy. This occurs through finding similar backgrounds and interests - interests in sports and teams, status coded clothing, baseball caps, schools and handbags to determine if the person is a member of a close socioeconomic class, interests in cultural experiences to see if they’re a member of an equal intellectual group… This is the trust building and rapport building process. In therapy, it could take some time; on the street we’re assessing people and clocking our fight/flight/freeze/fawn radar 100% of the time, under the hood.
The problem with contemporary dating is that we’re also checking for AUTHENTICITY, because nobody likes a phony. And I live in the City of Liars where name-dropping is de rigueur… famous friends, exclusive events, private dining clubs… success via osmosis… everyone desperately trying to escape the hoi polloi… “Life itself is will to power,” Nietzsche said. He didn’t realize that the Internet would gamify quotidien existence and spawn generations of fakers clamoring for “LIKEs”.
So on a first date each party is tracking for 1. trustworthiness and 2. authenticity. Here’s where the red flags emerge: if authenticity is tested before tribal trust is established, then it registers as oversharing. Here’s an analogy: I’ve been swimming a few times per week with two women for 6 years. We banter while resting in between laps. If they told me they were Trump-ettes it wouldn’t bother me at all because through our 6 years of chats we’ve established that we’re members of the same tribe - the cat-loving, movie-loving, health-nut, swimmers tribe. As I was fond of saying at Esalen, “It’s difficult to be an asshole when you’re naked.”
However, in Los Angeles, most people are obsessed with status so before you can ask them anything they’ll blurt out something like… “Just got back from Italy/Japan/London/Costa Rica… they have lie-down seats in Business Class!” They may as well ask to see your tax return. It’s so gross. They’re just testing to see how rich or poor you are. If someone tries to open a conversation with announcing a recent destination travel victory, I’ll usually counter with, “Just got back from Lompoc. The food in solitary isn’t what it used to be!”
As a therapist, I enjoy the luxury of hearing about these red flags from all age groups and sexes. Here are the top 50 red flags I’ve heard sorted by age group:
Age 15–22
Getting your meds right — finding the perfect cocktail of anti-anxiety, anti-depressant, and ADHD medication
Yeh, I’ve already stalked you on social media. “Who’s that person you were with in your stories last week? Just curious…”
Parental Clearance — whether or not your parents make you Uber when you do ketamine
Main Character Syndrome — narrating your life like there’s a camera crew following you around
Deciding to follow each other mid-date — granting permission to private socials
The Parent Trauma Olympics — competing over whose childhood was worse
Artist Pass for Coachella or just VIP?
Age 23–30
Body Count — how many people you’ve slept with, preferably of all sexes to show how woke you are, offered like a Chinese menu of promiscuity
How Hard You Work — proving worth through exhaustion, unprompted
Relationship Autopsy — performing forensics on the narcissist or borderline exs who ruined your life
Shopping Victories - the latest online consumer site offered like admission to an ‘Eyes Wide Shut” secret society
Healing Journey Update — a progress report on the life coaching program purchased six weeks ago
The 5-year Plan — reciting long-term goals even though you can’t decide which poke bowl to have for lunch
Wellness Regime — describing your supplements, smoothies, and Aura ring scores as if you were just nominated for an Academy Award
Burning Man? “Which camp?”
Age 31–40
Real Estate Zip Code Victories — comparing net worth disguised as small talk
Biological Clocks & Fertility Math — doing the arithmetic on eggs, sperm, and time out loud, “So, timeline-wise… in an ideal world…”
Therapy Speak Flex — “My therapist says I need to ‘lean in’ more…” (which is why I accepted your stupid offer to meet here).
Virtue Signaling — your volunteer trip and the soccer team for blind kids you founded in Compton
Status Coding —your gym (Equinox) and grocery store (Erewhon)
Wedding Tally — how many friends’ weddings you’ve attended this year
Career Pivot Justification — explaining why you left the “stable” job… (because it was soul-crushing)
Airline Frequent Flier Programs — which offers better (easier) upgrades and cooler lounges
Travel Oneupsmanship — the exclusive safari during which you were almost eaten alive, the masseuse’s name at some distant Aman resort, “PJs” (private jets)
Age 41–50
Divorce Lawyer Flex — comparing counsel like sommeliers compare vintages
Custody Logistics — your parenting schedule presented as a Navy Seals operation
The Ex Debrief — the whole marriage, in chronological order and 3 part harmony, including the late onset mental disorder from which your ex suffered
Alimony — mentioning what you pay or receive like you’re playing trivia at a pub
The Golden Handcuffs Confession — complaining about the job you hate that is too well-paying to quit
The Golden Shower Confession — c.f. Burning Man, above
The Second-Wind Wardrobe — explaining your new fashion choices as if they’re evidence of emotional growth
Age 51–60
Organ Recitals — reciting which vital organs are flagging
Supplement show-and-tell — comparing morning pill regimens for those flailing organs like teenagers compare playlists
Career Pivot — “I used to be in finance… now I make pottery and I’ve never been happier” (lying)
Surgery Résumé — comparing scars like they’re Purple Heart medals
Retirement Account — mentioning your broker as if they’re part of your extended family
Sleep Confessional — comparing thread-counts and mattress brands
Spending $500,000 to send your kid to college to learn coding. “Now what?”
Age 61–70
Joint Replacement Itinerary — recovery timelines recounted as if you’ll be ready for the next Olympics
Grandchild Portfolio Review — unsolicited pitch deck, slides include soccer trophies
Cruise Itinerary Comparisons — whose upcoming trip has the better buffets, magicians, and shore excursions
The Medicare Seminar — discussing supplemental coverage like it’s foreplay
The Late-life Dating App Tutorial — explaining, apologetically, how you even got here
Widow Etiquette — “Do you think it’s too soon for me to move on?”
Retirement Community Reconnaissance — comparing notes on which one has the best golf courses and Mah Jongg League
Age 71–80
Grief Inventory — comparing funerals of spouses
MD Rosters — whose specialist team has been on television
Assisted Living Reconnaissance — whether either of us is “there yet”
Hearing Aid Volume Wars — negotiating who speaks louder when they need to be understood
Legacy Talk — what you want to be remembered for, rehearsed and ready like a TED talk
For anyone over 80… you should probably skip the small talk and start with how lucky you are to be alive and how grateful you are for living so long.
For all of us under 80, I recommend suspending disbelief, creating adventures (museums, jazz clubs, lectures, classes) during which each party learns or discovers something new, and avoiding at all costs making first dates feel like auditions or interviews.
You can save the above list for second dates.
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