So Here's The Thing

This week's Dear Guyset episode covered everything from situationships and first texts to confidence, work-life balance, recurring relationship fights, and moving on from an ex.

At first, none of those questions seemed connected.

But after answering them, I realized they all came back to the same thing.

Most of the things we struggle with aren't actually about dating, work, or confidence.

They're about uncertainty.

We spend hours trying to figure out what someone else is thinking instead of saying what we're thinking. We convince ourselves the perfect text matters more than actually sending one. We replay old relationships because certainty feels safer than moving forward. Even at work, we convince ourselves things will eventually get better instead of acknowledging that they've already become too much.

One line from this week's episode kept coming back to me:

"Everything you're wondering about will reveal itself in how they respond."

If there was one lesson from this week, it's this:

Clarity almost always comes from action, not overthinking.

Five Things Worth Remembering

1. Situationships Stay Situationships Until Someone Speaks Up

One line from the episode summed it up perfectly:

"Undefined equals situationship. Defined equals relationship."

Nothing changes until someone is willing to have the conversation everyone is avoiding.

If you're constantly wondering where you stand, that uncertainty is already telling you something.

2. Stop Waiting To Send The First Text

The best advice from this week's episode wasn't about what to text.

It was about when to text.

"The best time to do most things is now."

If someone gave you their Instagram or their number, they're already interested enough to hear from you.

Don't let overthinking become the reason nothing ever happens.

3. Confidence Starts Before The Date

One listener asked whether they should manscape before a first date.

The real takeaway had nothing to do with grooming.

Confidence starts with preparation.

Getting the haircut. Wearing clothes you feel good in. Taking care of yourself. Showing up feeling like the best version of yourself.

Those things won't make someone like you.

But they'll help you walk into the date with confidence.

4. Believe People When They Choose You

One guy wrote in saying the girl he was talking to felt "out of his league."

Here's what I kept coming back to:

If someone keeps choosing you...

Believe them.

The fastest way to sabotage something good is convincing yourself you don't deserve it.

5. You Can't Move Forward While Constantly Looking Back

Checking your ex's Instagram feels harmless.

Until you realize you're reopening the same wound every single day.

You don't have to hate someone to stop following their life.

Sometimes moving on starts with creating enough distance to finally heal.

This Week, Try This

The next time you catch yourself trying to guess what someone else is thinking...

Ask them.

Text the person you've been thinking about.

Define the relationship.

Tell your partner what's been bothering you.

Tell your boss you've become overwhelmed.

Whatever conversation you've been avoiding, stop rehearsing it in your head and have it.

You may not get the answer you were hoping for.

But you'll finally have something real to respond to instead of another story you've created in your mind.

Three Things I Couldn't Stop Thinking About

"Everything you're wondering about will reveal itself in how they respond."

"Undefined equals situationship. Defined equals relationship."

"The best time to do most things is now."

And One Last Thing

One of my favorite parts about Dear Guyset is realizing that almost nobody is asking a truly unique question.

Every month, hundreds of guys wonder the same things.

They're wondering when to text.

Whether they're in a situationship.

If they're good enough for someone they're dating.

If work has taken over their life.

How to move on after a breakup.

The only difference is most people never ask.

That's why I started Guyset.

Not because I have every answer, but because I wanted to build a place where guys could ask the questions they thought they were the only ones asking.

If you've got one, send it in.

Chances are, someone else needs that answer too.

For More Guyset

This Week's Episode

Dear Guyset: Situationships, First Texts, Confidence & More

Read Next:

• What To Text After Getting Her Number (Exact First Texts To Send)

• Why So Many People Get Stuck in Situationships

• Why Modern Dating Feels More Confusing Than Ever

• The Modern Dating Timeline: Every Stage From the First Date to a Committed Relationship

Ask Me Anything

Reply to this email or submit your question at Guyset.com. It might be featured in a future Dear Guyset episode.

Thanks for reading, have a great week, and I'll see you next Tuesday.

Josh