A Brother just went through his Entered Apprentice degree last night. He’s sitting across from you at dinner before the next stated meeting, and you want to help him feel welcome and supported.
But what do you actually talk about?
Most Brothers default to the same basic questions:
“How are you doing with your proficiency?” “Do you have any questions?” Then awkward silence when he says “fine” and “not really.”
New Entered Apprentices need more than polite check-ins.
They need genuine conversation that helps them process what they experienced, understand what comes next, and feel like they actually belong.
Here are ten topics that create meaningful connection and actually help newer Brothers.
1. “What Part of the Degree Stuck With You Most?”
This is infinitely better than “did you like it?”
When you ask what stuck with him, you’re inviting him to share what resonated personally. Maybe it was a specific moment. Maybe it was something someone said. Maybe it was a feeling he can’t quite articulate.
Listen to what he shares. Then go deeper.
“Why do you think that moment stood out to you?”
“What do you think that symbol might mean?”
“I remember that part from my degree too. Here’s what I’ve come to understand about it over time.”
This conversation helps him process the experience instead of just moving past it. It shows you actually care about his thoughts, not just whether he’s making progress toward Fellowcraft.
2. “What Questions Do You Have That You’re Embarrassed to Ask?”
New EAs have dozens of questions they’re afraid to ask publicly because they don’t want to look stupid.
When you explicitly invite the “embarrassing” questions, you give permission to actually ask what he’s wondering.
“I still don’t understand what a Tiler does.”
“Why do we face East?”
“What’s the deal with the apron?”
These aren’t dumb questions. They’re foundational questions that every EA has.
Answer them clearly and without condescension. Share that you had similar questions. Make him feel normal for not understanding everything immediately.
This conversation builds trust and opens the door for him to keep asking questions as they arise.
3. “How’s Your Life Outside Lodge?”
This seems basic, but most Brothers never ask.
We talk about Lodge stuff constantly. Proficiency, upcoming meetings, ritual practice. We rarely ask about the actual lives Brothers are living.
Find out who this person actually is beyond being an Entered Apprentice.
What does he do for work? How’s his family? What’s occupying his time and energy right now? What’s hard in his life? What’s going well?
When you know someone’s real life, you can connect Masonic principles to their actual circumstances. You can check in meaningfully. You can be a Brother, not just a Lodge contact.
This conversation transforms him from “the new EA” to “Brother John who’s dealing with a tough situation at work and coaching his kid’s soccer team.”
4. “What Made You Want to Join Freemasonry?”
You probably heard his answer during his investigation, but ask again now that he’s been initiated.
His answer might be different after experiencing the degree.
Maybe his initial reason was curiosity or family legacy. Now he’s felt something deeper and can articulate why Freemasonry matters to him more clearly.
Or maybe his reason hasn’t changed, but hearing him share it helps you understand how to support him better.
“I joined because my grandfather was a Mason and I wanted to understand what was important to him.”
“I was searching for something and didn’t know what. I think this might be it.”
“I wanted male friendship and a sense of belonging.”
When you know why he joined, you can help him find what he’s seeking.
5. “What Do You Hope Gets Better About You Through Freemasonry?”
This is the “making good men better” conversation most Lodges never have.
If Freemasonry’s purpose is personal improvement, what does this Brother actually want to improve?
Maybe he wants to be more patient. Less angry. More disciplined. Better at communicating. More confident. More generous.
When he names something specific, you can help him work on it.
“I struggle with my temper. I want to learn self-control.”
Perfect. Now you know to occasionally check in: “How’s the temper thing going? Have you had situations that tested you? What helped?”
This conversation makes improvement real and personal instead of abstract and theoretical.
It also shows that you take the “making good men better” thing seriously, which sets a tone for his entire Masonic experience.
6. “Let Me Tell You About My Degree Experience”
New EAs often feel like they’re the only ones who were confused or overwhelmed or emotional during their degree.
Share your own experience honestly.
“I was terrified before my degree. Didn’t know what to expect and my imagination ran wild.”
“I barely remember parts of my EA degree because I was so overwhelmed. It took months before I understood what happened.”
“The thing that stuck with me most was…”
When you share your experience, you normalize whatever he’s feeling. You show that confusion, nervousness, and uncertainty are all part of the journey.
You also model vulnerability, which creates space for him to be vulnerable about his own experience and questions.
7. “Here’s What Helped Me Most as a New EA”
Give him practical guidance based on what you wish someone had told you.
Maybe you wish someone had emphasized studying between degrees instead of just memorizing proficiency.
Maybe you wish someone had encouraged you to attend everything possible in your first six months.
Maybe you wish someone had told you it’s okay to be confused and that understanding develops over time.
Share the specific thing that helped you most, and why.
“The best thing I did was find two other EAs and we met monthly to discuss what we were learning. Having peers at the same stage made everything easier.”
“I started keeping a journal after each Lodge meeting. Writing down thoughts helped me process things I didn’t understand.”
“An older Brother took me to coffee weekly and answered every question I had. That mentorship changed my entire experience.”
This conversation gives him actionable ideas for making the most of his time as an EA.
8. “How Can I Actually Help You?”
Most Brothers offer vague support: “Let me know if you need anything.”
The new EA nods politely and never asks for help because he doesn’t know what he needs or feels awkward asking.
Be specific about how you can help.
“I’m happy to meet weekly to help with proficiency work if that would be useful.”
“I can answer questions about symbolism and what things mean whenever you’re confused.”
“If you want someone to grab coffee with outside of Lodge and just talk about Masonic stuff, I’m available.”
“I can introduce you to other Brothers and help you feel less like an outsider.”
When you offer specific, concrete help, he’s more likely to take you up on it.
And when he does, you actually create the mentorship relationship every new EA needs but most never get.
9. “What Concerns Do You Have About Freemasonry?”
Give him permission to voice concerns without judgment.
Maybe he’s worried about time commitment. Or cost. Or whether he’ll fit in. Or what his wife thinks. Or whether it’ll be worth it.
These concerns are normal and addressing them helps.
“I’m worried this will take more time than I have with young kids.”
Good to know. Now you can talk realistically about time commitment, help him set boundaries, and show him how other fathers balance Lodge and family.
“I’m concerned I won’t fit in because everyone’s so much older.”
Valid concern. Now you can introduce him to the few younger Brothers, help him find common ground with older ones, and be intentional about including him.
When concerns stay unvoiced, they fester and eventually drive people away. When they’re discussed openly, they can often be addressed.
10. “Who Should You Get to Know Better in This Lodge?”
New members often don’t know who to connect with beyond their mentor.
Make strategic introductions.
“You mentioned you work in IT. Brother Mike does too. You should talk to him.”
“You said you were interested in Masonic history. Brother Tom is our Lodge historian and would love to talk about that stuff.”
“You’re around the same age as Brothers Steve and John. Let me introduce you.”
Strategic introductions help him build relationships beyond just one mentor. They show him there are multiple people he can connect with. They help him find his place in the Lodge community faster.
After introducing him, follow up: “Did you get a chance to talk with Brother Mike? What did you think?”
Why These Conversations Matter
Notice what these ten topics have in common: they’re all about actually getting to know the person and helping him integrate meaningfully.
They’re not about proficiency progress or ritual procedures. Those conversations are necessary, but they’re not sufficient for creating genuine connection and support.
New Entered Apprentices need Brothers who care about them as people, not just as candidates to move through degrees.
When you have these deeper conversations, several things happen:
You build real relationship instead of superficial acquaintance.
You help him feel less isolated and more connected.
You show him what Brotherhood actually looks like.
You give him reasons to stay involved beyond just completing degrees.
You become someone he can actually turn to for support.
This is how retention happens. Not through better recruitment, but through better relationship.
The Follow-Up Matters
Having one good conversation isn’t enough. Follow-up is what transforms a single interaction into genuine mentorship.
Text him later that week: “Hey, how’s the proficiency work going? Need any help?”
Check in about the concern he voiced: “You mentioned worry about time commitment. How’s that feeling after a month?”
Introduce him to the Brother you said you would.
Invite him to things outside of stated meetings: “Few of us are grabbing coffee Saturday morning. Want to come?”
Consistency creates connection. One conversation creates a moment. Regular engagement creates relationship.
For Mentors and Every Brother
If you’re an assigned mentor, these conversations are your job. Have them regularly and intentionally.
But even if you’re not the official mentor, you can still have these conversations. Every Brother should help newer members feel welcome and supported.
The EA in your Lodge doesn’t need one mentor. He needs a whole Lodge of Brothers who care about his growth and integration.
Be one of those Brothers.
Next time you see the new EA sitting alone at dinner or standing awkwardly before a meeting, go talk to him. Not about proficiency or Lodge business, but about him as a person and his experience as a new Mason.
Use these ten topics. See what happens.
You might become the Brother who makes the difference between him staying engaged for decades or disappearing within a year.
That’s worth a conversation.
New Entered Apprentices often feel isolated and confused, even in Lodges full of friendly Brothers…
If you’re an EA looking for more guidance and connection with others at your stage, or if you’re mentoring new members and want resources to support them better…
The Freemasons Community brings together hundreds of Entered Apprentices, Fellowcrafts, and supportive Master Masons.
Ask questions without judgment, connect with peers going through the same journey, and get the depth of support your local Lodge might not be providing. The mentorship every EA deserves is available.
You just have to reach for it.