Relationship Insights: 5 Must-Ask Questions Before Your First Date
A Permission to be Powerful Premium Post
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Dear Permission to be Powerful Reader,
There are five questions I believe everyone should explore before going on a first date.
Not in a job interview tone.
Not in a “grill them for answers” way.
But in an emotionally intelligent, curious, playfully investigative way.
These five questions are designed to give you quick insight into how a person lives, relates, copes, and connects—so you can filter fast, waste less time, and avoid heartbreak you never needed to sign up for.
Let’s dive in.
1. 🧩 Hobbies
“So what do you get into when you’re not working?”
This tells you:
If they have an inner life
If they’re comfortable being alone
If they expect you to become their everything
If they have no hobbies or interests… that’s data.
If they light up when they talk about them… that’s data too.
2. 👨👩👧 Family
“Are you close with your family?”
“Any fun family traditions?”
“Do you see your parents often?”
These subtle questions can tell you:
How they speak about important people
Whether they carry old resentment or unresolved trauma
If they know how to hold intimacy or still run from it
You don’t need their whole history.
You just need a window into how they show up in emotional bonds.
3. 💡 Addictions
“What’s something you probably spend too much time on?”
“Any guilty pleasures or vices?”
This one’s tricky—but essential.
You’re not asking “Are you an addict?”
You’re checking for self-awareness, honesty, and how they manage emotional overwhelm.
Watch how they answer. Or dodge. Or laugh it off.
Addictions (to substances, social media, porn, work, even validation) often show up in subtle ways.
4. 🐾 Pets
“Do you have pets?”
Sounds simple, right?
But how someone treats animals can reveal a LOT:
Can they care for another being?
Do they like consistency, affection, and routine?
Or do they get overwhelmed by responsibility?
Pets can be a proxy for how someone handles real-life intimacy. You’d be surprised.
5. 👥 Friends
“Who do you hang out with the most?”
“Do you still keep in touch with childhood friends?”
This helps you gauge:
Their emotional support system
Their ability to maintain healthy connections
Whether they’re relational… or isolated
If they have no close friends, or only speak about others with drama or distance, that’s worth paying attention to.
Practice the Questions, Watch the Patterns
These aren’t “yes/no” vetting tools.
They’re starting points—data-gathering moments.
Signals, not answers.
Try them out with friends or strangers. Refine your delivery. Notice how people respond.
Because getting good at reading someone clearly before your heart is on the line?
That’s one of the highest forms of self-love.
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You’re not too picky.
You’re just finally asking the right questions.
Zalman, LCSW
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