25 Dating Red Flags That Scream 'Run Away' (Based on Real Stories)
After surviving 25 catastrophic relationships and writing a book about it, I've learned to spot red flags from a mile away. Here are the warning signs that should send you running—backed by real, cringe-worthy stories.
Let me start with a story. Picture this: It's our third date, and he asks me to lie to my parents about where we're going because he's "not ready to meet them yet." Red flag? Absolutely. Did I ignore it? You bet I did.
That relationship lasted six months too long and ended with him asking me to cosign a loan for a motorcycle. Spoiler alert: I didn't, and he called me "financially unsupportive."
Here's the thing about red flags—they're usually bright red and waving frantically, but we're often too hopeful, too lonely, or too invested to see them. After documenting my worst dating disasters in "The Worst Boyfriends Ever," I've identified the 25 biggest warning signs that should send you sprinting in the opposite direction.
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Early Warning Signs (First Few Dates)
They're Rude to Service Workers
If someone treats waiters, baristas, or retail workers poorly, they're showing you exactly how they'll treat you once the honeymoon phase ends. I once watched a date yell at a teenage barista over a $4 latte. That should have been date #last.
They're Always the Victim in Every Story
Every ex was "crazy." Every boss was "unfair." Every friend "betrayed" them. If everyone in their life is allegedly the problem, they're probably the problem.
Love Bombing (Too Much, Too Fast)
"You're the most amazing person I've ever met" on date two is not romantic—it's a red flag. Real love develops over time, not in a weekend.
They Push Physical Boundaries
If they can't respect a simple "no" to hand-holding or kissing, they won't respect bigger boundaries later. Trust me on this one.
Think You've Experienced These Red Flags?
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🎯 Play Bad Date BingoControl & Manipulation Tactics
They Want to Know Where You Are 24/7
Constant texting isn't cute—it's controlling. If they need minute-by-minute updates on your whereabouts, that's surveillance, not love.
They Isolate You from Friends and Family
First, your friends are "bad influences." Then your family "doesn't understand" you. Before you know it, you're cut off from your support system. Classic abuser playbook.
Financial Manipulation
They "forget" their wallet, borrow money constantly, or worse—expect you to pay for everything because "they're between jobs." Again.
Frequently Asked Questions
How many red flags are too many?
Honestly? One major red flag is enough to reconsider a relationship. You're not collecting them for a prize—you're evaluating someone's potential as a life partner.
What if they promise to change?
Words are wind. If someone shows you who they are repeatedly, believe them. Change is possible, but it requires consistent action over time, not just pretty promises.
Should I give someone a second chance after seeing red flags?
Depends on the flag. Chronic lateness? Maybe. Disrespecting your boundaries? Absolutely not. Trust your gut—it's usually right.
Want the Full Story?
These are just 5 of the 25 red flags I detail in my audiobook. Get the complete guide to spotting disasters before they ruin your life—plus 25 hilarious (and cautionary) stories of what happens when you ignore the signs.
About Aleks Filmore
Aleks Filmore is an indie LGBTQ author who writes about love, loss, and aftermath with sharp wit and emotional realism. His breakout memoir-in-essays, The Worst Boyfriends Ever, turned private chaos into connection and became a sleeper hit, reaching #1 in several Amazon rankings and earning praise from readers for its wit, candor, and painfully accurate portraits of modern dating.