The Questions Guys Ask But Never Say Out Loud
Clear answers to common dating questions about interest, readiness, and communication
By
Josh Felgoise
Dec 16, 2026
Wicked
There are certain questions guys carry around that never quite find a place to land.
They are not dramatic enough for a breakup conversation.
Not serious enough for therapy.
Not casual enough for a group chat.
So they sit there. Unasked. Unanswered.
That is why Dear Guyset exists.
Not to give perfect advice. Not to act like I have everything figured out. But to talk through the stuff most guys are quietly wondering about and pretending they are not.
As I said in the episode, “This is just one guy’s perspective. One guy’s opinion. One guy’s thoughts.” And honestly, that is usually all we need. Someone to say, I have been there too.
So let’s talk about it.
Farting in a Relationship Is Way More Emotional Than It Should Be
The question that kicked this episode off sounds ridiculous on the surface.
How do you handle farting in a relationship?
But the reason it matters has nothing to do with bodily functions. It has everything to do with vulnerability.
Early in relationships, most guys are doing mental gymnastics to avoid being seen as gross, human, or too real too soon. I have been the guy who goes into the bathroom, turns on the sink, the fan, maybe even the shower, and orchestrates a full soundscape just to hide the fact that I am a human being with a digestive system.
And if that makes you feel more comfortable early on, that is fine.
There is no rulebook for when you are allowed to be fully yourself. Comfort comes first. Always.
But here is the part we avoid saying. The longer you pretend you are not human, the bigger the moment becomes later. Eventually, the thing you are trying to hide becomes the elephant in the room.
Everybody farts. Everybody poops. And the real question is not when you let it rip. It is how safe you feel being fully seen by someone else.
Research from Psychology Today has shown that early vulnerability is one of the biggest predictors of long-term intimacy. Humor, honesty, and shared humanity matter more than perfect timing.
Sometimes the easiest way through awkwardness is a joke. A shrug. A moment of shared humanity. The goal is not perfection. It is ease.
When a Girl Likes Your Instagram Story, Yes, It Usually Means Something
We live in a strange social era where liking an Instagram story has become a form of communication.
Not a message. Not silence. Something in between.
So when guys ask, what does it mean if she liked my Instagram story, they are really asking something deeper.
Am I imagining this?
Am I reaching?
Is this interest or coincidence?
In most cases, it is interest.
It is a low-pressure way of saying, I am open to talking. The ball is in your court.
Is it guaranteed? No.
Is it a proposal? Also no.
But it is not nothing.
The key is context. How well do you know her? Has there been chemistry before? Has there been conversation? A story like from someone you barely know often means more than one from someone you talk to all the time.
If this question spirals you, the mindset shift in How To Stop Overthinking Everything helps you separate signal from noise without reading too much into every micro-moment.
If you want to respond, respond. Reaching out is not weak. It is clear.
“I’m Not Ready for a Relationship” Hurts No Matter the Reason
One of the hardest questions in the episode was also one of the most common.
She said she is not ready for a relationship. Is that a cop out?
Here is the honest answer. It does not really matter.
The reason someone gives matters far less than the reality that they are ending something. Whether it is fear, timing, lack of interest, or emotional exhaustion, the result is the same.
It is over.
And that sucks.
The mistake most guys make is turning that ending into a puzzle they feel responsible for solving. What did I say wrong? What could I have done differently? What if I texted faster or slower?
Sometimes there is no answer that gives peace.
This is the same emotional trap I unpack in Getting Ghosted Hurts, But It Might Be the Best Thing That Happened to You. Silence and rejection are not reflections of your worth. They are information.
The healthiest response is respect. You can leave the door open kindly. You can say you enjoyed your time. But you do not need to chase clarity from someone who is stepping away.
Rejection does not mean you are unlovable. It means this was not the place you were meant to land.
If You Are Wondering If You Are Ready for a Relationship, You Probably Are
This question hit close to home because I have lived it more than once.
How do I know if I am ready for a relationship?
Most guys asking this are not avoidant or cold. They are anxious. They are afraid of messing something good up. Afraid of not measuring up. Afraid of losing control of a life that already feels full.
And that fear usually comes from caring.
Here is the truth most guys never hear. You will never feel fully ready. Readiness is not a feeling you wait for. It is something you grow into by trying.
You cannot rehearse intimacy in your head. You cannot think your way into emotional preparedness.
This is why the idea behind High Expectations, Loosely Held matters so much. You can want something real without gripping it so tightly that it breaks.
If you are asking this question, it means something matters. And that is a good sign.
Communication Fixes More Than We Admit
One of the final questions was about something deceptively simple.
My girlfriend never plans dates. How do I ask her to plan more?
The answer is not confrontation. It is curiosity.
Most resentment in relationships comes from unspoken expectations. From assuming the other person knows what you want. From holding frustration quietly and letting it turn into distance.
People cannot read your mind.
Studies summarized by The Gottman Institute show that couples who frame needs as shared goals rather than complaints build far more trust over time.
You can ask in a way that invites effort instead of demanding it. You can create space for shared planning instead of silently keeping score.
Communication does not have to be dramatic to be effective. It just has to be honest.
The Point of All of This
None of these questions are small.
They are about vulnerability.
Self-worth.
Rejection.
Connection.
They are about learning how to be human with someone else without losing yourself in the process.
As I said in the episode, “Guys don’t really talk about their shit.” And that silence costs us more than we realize.
If you saw yourself in any of these questions, you are not behind. You are not broken. You are just paying attention.
And that is where growth actually starts.
FAQ
Why do guys struggle to talk about these things?
Because most men were never taught how to talk about vulnerability without feeling weak.
Is it normal to overthink small moments in dating?
Yes. Especially when something matters to you. Overthinking is common, not a flaw.
Does social media actually affect dating confidence?
Yes. Mixed signals and passive interactions create uncertainty, which fuels anxiety.
How do I know when to speak up in a relationship?
When something keeps bothering you quietly, that is usually your cue.
Are these questions signs I’m insecure?
No. They are signs you care and are becoming more self-aware.










