Advice for my single friends: The New Rules of Texting, Dating & Flirting in Midlife
(Because Apparently, the Thumbs-Up Emoji Means ‘I’m Mad at You’ Now?)
Let’s be honest—dating, texting, and flirting in midlife is not for the faint of heart. You thought raising kids was hard? Try deciphering a text that just says, “K.”
Dating in your 40s and 50s is like using a smartphone with a flip-phone soul. We grew up passing notes in class, calling our crush’s house and praying their mom wouldn’t answer, and waiting an entire week to hear a voice on the answering machine (Hi, it’s me… again). But now? Oh no, now there are rules. Unspoken, baffling, often ridiculous rules that no one warned us about.
So, let’s break it down—the new, absurdly complex, and hilariously frustrating world of midlife flirting and texting.
Rule #1: The Emoji Language Barrier
What we think:
• A thumbs-up means: Sounds good!
• A heart means: Aw, that’s sweet!
• A winking face means: Playful and flirty!
What THEY think:
• A thumbs-up means: Passive-aggressive and dismissive.
• A heart means: Whoa, whoa, whoa. Are we in love now?
• A winking face means: Call the authorities.
Apparently, the safest way to text now is to write everything like a corporate email—“Per my last message, I think you’re cute and available for dinner Friday.”
Rule #2: The Three-Day Texting Window
Back in the day, you waited three days before calling someone so you didn’t seem desperate. Now, the rule is:
• Text too soon? You’re unhinged.
• Wait too long? You’re playing games.
• Forget to text at all? You’re obviously in the Witness Protection Program.
Meanwhile, you’re just trying to remember where you left your reading glasses so you can actually see the damn screen.
Rule #3: The Mystery of the “Read Receipts”
Do you turn them on? Off? Who even knew this was a thing?
• If they see you read the message but don’t respond? You’re a monster.
• If you don’t read it right away? You’re ignoring them.
• If you read it and respond too quickly? You need to calm down.
The only way to win? Send a pigeon. Everyone loves a good carrier pigeon.
Rule #4: The Art of Flirting Without Sounding Like a Boomer
Flirting used to be simple—flip your hair, laugh a little too hard, and let them win at pool (even though you were a shark). Now? It’s all about the text game.
Bad Flirting in 2025:
• “U up?” (Sir, it’s 9:45 p.m. I’m in bed with melatonin and an ice pack.)
• “Looking good, lol.” (Why are we laughing? Is this an insult? Am I supposed to be flattered or offended?!)
• “We should hang out sometime.” (Sometime? Sometime WHEN, Brian? This week? Next year? After menopause?!)
Better Flirting in 2025:
• “I saw a dog that looked exactly like yours today. It made me think of you and smile.” (Awww.)
• “Just heard [insert favorite band] is coming to town. Want to go pretend we’re still 25?” (Yes!)
• “I made an elaborate excuse to text you instead of just admitting I wanted to talk. Hope it worked.” (Well played, sir.)
Rule #5: The Voice Note Ambush
Nothing sends a chill down the spine quite like opening a text thread and seeing: “(Voice Message - 47 seconds).”
Do you:
a) Panic and throw your phone across the room?
b) Pretend you didn’t see it and respond with “haha yes!!” hoping that fits?
c) Grab your reading glasses, crank the volume, and pray it’s not awkward breathing?
(Pro tip: It’s always awkward breathing.)
Rule #6: The Accidental Screenshot
The moment of sheer terror when you accidentally screenshot a conversation and it sends them a notification. Congratulations, you now look like a full-blown private investigator. Hope you enjoy explaining why you just saved a picture of their “Hey, what’s up?” text like it’s evidence in a federal case.
Rule #7: The Sudden Disappearance (a.k.a. Ghosting, But With Back Pain)
At this age, when someone disappears from texting for a few days, you don’t assume it’s ghosting. You assume:
• They fell asleep at 8 p.m. and forgot.
• They’re on a three-day ibuprofen regimen for a mild injury.
• They lost their reading glasses again and can’t see their phone.
Give it time. They’ll be back after their chiropractor visit.
Final Thoughts: Keep Laughing, Keep Texting, Keep Dating
Dating and texting in midlife is chaos, but at least it’s entertaining. We may not understand every rule, but we do know that real connection isn’t about perfect emojis or response times—it’s about laughing, having fun, and finding someone who texts back before bedtime.
So, keep flirting, keep texting, and if all else fails—just send a pigeon.