How to Know Which Friendships Are Worth Going Deeper With (and Which Are Better Left Light)

You’ve outgrown “just being included.” You’re craving friendships that feel like a two-way street, not ones where you’re overanalyzing texts or wondering if you were too much.

But how do you actually figure out who’s worth investing in emotionally and who’s better kept as a group friend, casual acquaintance, or brunch-only buddy?

Here’s how to tell and the exact words to help you figure it out.

First: Know What You’re Actually Looking For in a Friendship

You’re not asking for too much. You’re looking for:

• Emotional safety, not just shared plans

• Mutual effort, not just convenience

• Depth, not just gossip or vague updates

Friendships worth investing in show consistency, care, and emotional openness. Casual ones can still have a place, but they don’t deserve your vulnerable energy.

Use This 3-Part Filter to Assess the Friendship:

1. Do I feel emotionally safe around them?

Ask yourself:

• Do I censor myself or overthink everything I say?

• Do I leave feeling more relaxed or more judged?

-If you feel like you can exhale and be yourself, that’s a green light.

-If you leave feeling like you performed, hosted, or managed, it might be better kept casual.

2. Do they show curiosity about my inner world or just react to surface updates?

Try this test the next time you talk:

“Hey, I’ve been trying to check in on how people are really doing lately not just the busy stuff. How you’ve been doing lately but really doing?”

-If they respond with openness or mirror the effort, that’s a sign of real connection.

-If they change the subject or keep it vague, they might not be available for that kind of depth.

3. Do they follow up without being prompted?

It doesn’t have to be constant but intentional people will circle back.

• “How did your appointment go?”

• “You mentioned that tough convo, how are you feeling?”

-Small moments like these signal you’re seen.

-If it’s always you following up, or you’re only contacted when they need something, take note.

Phrases to Use If You Want to Test the Depth

If you’re unsure how to gauge emotional availability without seeming awkward or needy, try:

• “I’ve been trying to be more intentional lately with my friendships, what’s been on your mind outside of the usual day-to-day busyness?”

• “I’ve noticed we usually share updates, but I’ve been craving more real conversations. Is it okay if we talk about something that’s been on my heart?”

These small shifts act as both a signal and a filter:

If they lean in, it’s a sign you can explore a deeper connection.

If they pull back, you have your answer without overgiving.

Here’s What to Say to Yourself if It Stays Surface-Level

If someone can’t meet you there, it doesn’t make them a bad friend. But it does mean you might want to stop expecting closeness where it isn’t naturally present.

Tell yourself: “Not every friend has to be a deep friend. I can keep things light without sacrificing my need for depth, I just give that energy to someone else.”

Your Final Takeaway: 

Friendships worth going deeper with don’t make you work so hard to feel seen. The ones that are better left light? They’ll show you with their silence, surface talk, or lack of reciprocity. This isn’t about cutting everyone off. It’s about noticing where you feel safe to go deeper and honoring that inner nudge.

Have a specific question? Head to the forum and ask away, I’ll reply with tailored support!

Xo,
Dr. C