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.
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. 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 had differing political beliefs 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, morning swimmers tribe. As I was fond of saying at Esalen, “It’s difficult to be an jerk when you’re naked.”
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 Second-Wind Wardrobe — explaining your new fashion choices as if they’re evidence of emotional growth
- All Original Parts? Or has been some retrofitting?
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.