LESSON #12 — Dark-Side First Date Questions
- Loretta & David Allseitz
- Dec 29, 2025
- 4 min read
AKA: Ask better questions. Waste less time.
PREVIOUS LESSON QUIZ ANSWER
Before we get into today’s lesson, let’s close out the quiz from Lesson 11.
You were asked what to do when someone gives you a story that doesn’t quite add up — especially during Christmas, when everyone’s expected to be extra nice, forgiving, and willing to “keep the peace.”
The correct dark-side answer?
A.
A) Ask questions so it makes sense.
(Not to argue. Not to accuse. To watch where the story starts tripping over itself.)
Because here’s the truth:
Lies survive on silence, politeness, and people filling in gaps for them.
Questions remove the padding.
Which brings us to today’s dark-side survival skill…
LESSON #12 — Dark-Side First Date Questions
If Lesson 11 taught you how confidence exposes bullshit,
Lesson 12 teaches you how to avoid it entirely.
Because once you stop giving people the benefit of the doubt they haven’t earned,
you also stop asking useless questions.
First dates aren’t about chemistry.
They’re about information.
Let’s break it down, dark-side style.
Why First Dates Lie to You
Most first dates are performances.
Everyone’s:
chill
easygoing
low-maintenance
on their “best behavior”
And then six months later people are shocked they’re dating someone emotionally unavailable, conflict-avoidant, and allergic to accountability.
The problem isn’t dating.
It’s the questions.
Normal questions tell you what someone likes.
Dark-side questions tell you how someone:
handles conflict
repeats patterns
manages expectations
creates resentment
In other words: who they actually are once the vibe wears off.
Why “Normal” People Don’t Ask These
Because these questions:
don’t flatter
don’t perform
don’t protect egos
They expose patterns.
And patterns don’t care about chemistry.
If someone gets uncomfortable when you ask real questions, that’s not a red flag.
That’s data.
How to Use These Questions Without Making It Weird
You don’t fire them off like an interrogation.
You sprinkle them in.
You laugh.
You answer too.
They work because they sound casual — but they land deep.
(And yes, if you don’t want to remember them mid-drink, there’s a printable version at the bottom of this post. You’re welcome.)
The Dark-Side First Date Questions
These are the ones “normal” people wouldn’t dare ask —and the dark side knows tell you everything you need to know.
1. “What’s something you keep swearing you won’t repeat… but kinda do?”
Everyone has a pattern.
You’re not listening for perfection.
You’re listening for awareness.
If they say “nothing,” they’re lying.
If everyone else is always the problem, congratulations — you’re next.
2. “When you’re pissed, are you silent, spicy, or dramatic?”
This tells you how fights will go without having one.
Silent = withdrawal
Spicy = reactive
Dramatic = escalation
None are dealbreakers by default.
Pretending you don’t fight is.
3. “What’s a flaw you’re tired of defending?”
This cuts through fake self-awareness fast.
Real answers sound honest.
Fake answers sound branded.
If they say “I care too much,” drink your drink and take notes.
4. “What do you expect without asking for?”
Everyone has unspoken expectations.
Communication.
Consistency.
Effort.
Reassurance.
If they can’t name theirs, you’ll be guessing forever — and losing arguments you didn’t know you were in.
5. “When life goes sideways, how do you usually handle it?”
This tells you whether their chaos eventually becomes your unpaid job.
Problem-solving is attractive.
Spiraling is human.
Avoidance is expensive.
Choose wisely.
6. “What do you care about that most people don’t?”
This is a values check disguised as curiosity.
Watch their energy.
Do they light up?
Get specific?
Actually care?
Compatibility lives here — not in favorite movies.
7. “What’s something you put up with longer than you should have?”
This shows you their tolerance level.
And whatever they tolerate?
You will eventually be expected to tolerate too.
Endurance isn’t a virtue when it replaces growth.
8. “What’s something you won’t compromise on anymore?”
This is maturity in question form.
Healthy answers come from experience.
Bitter answers come from wounds.
Rigid answers come from fear dressed up as strength.
Listen to the why.
9. “What’s something you expect that you don’t always communicate?”
This one separates adults from future resentment factories.
Unspoken expectations don’t disappear.
They turn into silent scorekeeping.
10. “What’s something about you that’s hard to date?”
Everyone has a cost.
People who know theirs are safer.
People who joke it off aren’t ready.
People who get offended just saved you six months.
The Dark-Side Dating Truth
These questions don’t ruin dates.
They ruin bad matches early.
People who are aligned will:
laugh
answer honestly
ask questions back
People who aren’t will:
deflect
minimize
say “wow, that’s intense”
Good.
You’re not auditioning.
You’re disqualifying.
Want These Questions in One Place?
I put all of these into a clean, printable Dark-Side First Date Questions sheet so you don’t have to screenshot this post or rely on memory after a drink or two.
Grab it below.
Use it responsibly.
Or irresponsibly. I’m not your mother.
Missed Previous Lessons? Check them out here: Lessons from the Dark Side 💀
Villains Welcome.
*If you’re drawn to dark truths and the stories they leave behind, start with The Dollmaker of Point on Amazon.
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