The Ultimate Dating Disaster Survival Guide: What Not to Do (According to Someone Who Did It All)

8 min read September 6, 2025 By Aleks Filmore

Listen, I've made every dating mistake in the book. And then I wrote a book about it. Consider this your crash course in what NOT to do, courtesy of someone who face-planted through the dating world so you don't have to.

Chapter 1: The "I Can Fix Him" Fallacy

Let me paint you a picture: It's 2019, I'm in my 30s, and I meet this guy who thinks emotional intelligence is a type of smartphone app. Red flags? I collected them like Pokémon cards. His apartment looked like a tornado hit a GameStop, he hadn't washed his sheets since the Obama administration, and he once asked me if feminism was "still a thing."

But did I run? Oh no. I saw "potential." I thought, "Maybe he just needs the right man to inspire him!" Spoiler alert: I am not Bob the Builder, and broken men are not renovation projects.

🚨 Survival Tip #1

If you find yourself making excuses for someone's behavior to your friends, that's not love—that's being a PR manager for a terrible client.

Chapter 2: The Oversharing Olympics

Picture this disaster: First date, nice restaurant, everything's going well. Then I decided to share my entire emotional autobiography, including my fear of commitment, my therapy revelations, and my complicated relationship with my mother. By dessert, I had basically handed him my psychological profile and asked if he wanted to be my unpaid therapist.

He looked like a deer in headlights. Can't say I blame him—I had basically trauma-dumped a novel's worth of backstory before we'd even shared appetizers.

💡 Survival Tip #2

Save the deep emotional revelations for after you know their last name and whether they believe in basic hygiene.

Chapter 3: The Text Message Spiral of Doom

Oh, the texts. THE TEXTS. I once sent a guy 47 messages in a row because he didn't respond to my "good morning" text for three hours. Forty-seven! It started with "Hey, did you see my message?" and escalated to "I'm writing a thesis on why modern communication is failing us as a society."

By message 23, I was questioning whether he was dead. By message 35, I was questioning my own sanity. By message 47, I was single again. Shocking, I know.

📱 Survival Tip #3

If you're sending more messages than a 13-year-old with their first crush, put the phone down and go touch some grass.

Chapter 4: The "Playing It Cool" Catastrophe

After my oversharing phase, I swung hard in the opposite direction. I became so "chill" I was practically frozen. A guy could have proposed marriage and I would have responded with "Yeah, maybe, whatever works." I thought being mysterious meant being completely unavailable, emotionally and otherwise.

Turns out, there's a difference between being mysterious and being a human equivalent of a shrug emoji. Who knew?

🎭 Survival Tip #4

There's a sweet spot between "overly eager golden retriever" and "emotionally unavailable house cat." Find it.

Chapter 5: The Dating App Personality Crisis

I created so many different versions of myself on dating apps, I basically became a one-man repertory theater. On Bumble, I was "adventure-seeking hiking enthusiast" (I had been hiking exactly once). On Tinder, I was "laid-back Netflix and chill guy" (anxiety levels: actually through the roof). On Hinge, I was "sophisticated wine connoisseur" (I knew the difference between red and white, and that was about it).

Plot twist: None of these people were actually me. I was like a dating catfish, except I was catfishing myself.

🎪 Survival Tip #5

Be yourself, even if yourself is a hot mess who quotes reality TV and eats cereal for dinner sometimes. The right person will find that endearing.

The Recovery: What Actually Works

After systematically destroying my dating life through every method possible, I finally learned some things that actually work:

1. Standards Are Not Suggestions

Having standards doesn't make you picky—it makes you someone who values themselves. If someone can't meet basic requirements like "has a job" and "doesn't live in their mother's basement by choice," that's information, not a character flaw on your part.

2. Red Flags Are Not Decorative

When someone shows you who they are, believe them the first time. Red flags aren't there to add color to the relationship—they're warnings, not party decorations.

3. You're Not a Rehabilitation Center

You cannot love someone into being a better person. You're looking for a partner, not a project. Save the fixing for your credit score, not your love life.

4. Communication Is Key (But So Is Timing)

Be honest about what you want, but maybe don't lead with your five-year plan and baby names on the first date. There's a time and place for everything, and that time is usually not within the first hour of meeting someone.

The Plot Twist

Here's the thing about dating disasters: they make the best stories. Every terrible date, every cringe-worthy text exchange, every moment I wanted to disappear into the floor—they all became material for my book, "The Worst Boyfriends Ever."

Sometimes the journey is messy, embarrassing, and filled with more red flags than a Communist parade. But it's YOUR journey, and it's leading you somewhere. Even if that somewhere is just to a place where you can laugh about it later and help other people avoid the same potholes.

Ready for More Dating Disaster Stories?

If you enjoyed this survival guide, you'll love my audiobook "The Worst Boyfriends Ever" - where I share even more cringe-worthy dating stories and the lessons I learned from each spectacular failure.

Listen to More Disasters →

Final Survival Wisdom

Dating is weird, people are complicated, and sometimes you're going to make choices that will make you question your own judgment. That's normal. That's human. That's material for great stories later.

The goal isn't to be perfect—it's to be authentic, learn from your mistakes, and hopefully find someone who thinks your particular brand of chaos is charming rather than concerning.

And if all else fails, you can always write a book about it. Worked for me.