Dating as a Growth Journey

Small Group Workbook

Session Overview and Goals

This workbook is designed for 2-3 small group sessions (60-90 minutes each). It can be condensed into fewer sessions or expanded with additional discussion time.

Session 1: Taking Ownership — Rethinking Your Approach to Dating Session 2: Getting Active — Practical Steps and Facing Your Fears Session 3: Growing Yourself — Internal Work for External Results

What You'll Walk Away With:

• A reframed understanding of dating as growth journey, not a trophy hunt
• Practical strategies for expanding your world and meeting new people
• Awareness of internal patterns that may be sabotaging your dating life
• Honest conversation with others navigating the same challenges
• Concrete next steps for your dating life

Session 1: Taking Ownership

Rethinking Your Approach to Dating

Teaching Summary

There are really only two kinds of dating problems: either you're not getting dates, or you're getting dates but none of them are turning into something meaningful. Both problems have answers — but finding those answers requires taking ownership.

Many people — especially in Christian circles — adopt a passive approach to dating. They believe God will simply "bring the right person" into their lives. They wait. And they wait. And the waiting turns into years. But here's the question worth asking: What if God has brought ten great people into your life already, and you weren't able to recognize them or make it work? Is that God's fault, or is there some responsibility on your side?

You wouldn't expect a job to show up without effort. You didn't find your church by sitting at home. Dating requires the same kind of intentional engagement. This isn't a lack of faith — it's stewardship of your life.

The second shift is even bigger: dating is not about finding "the one." When we approach dating as a safari — hunting for a trophy with a specific image in our heads — we create all kinds of problems. We eliminate people too quickly. We bring pressure that kills genuine connection. We see each unsuccessful date as a failure rather than a learning experience.

What if, instead, dating was a journey of learning about yourself, about relationships, and about other people? What if every date — whether it led somewhere or not — was an opportunity to grow, to discover what you actually value, and to become the kind of person who could sustain a healthy relationship?

This isn't lowering your standards. It's raising your approach. The people who find healthy, lasting relationships aren't the ones who found the perfect person on the first try. They're the ones who embraced a growth process, stayed engaged, and eventually recognized something good when they found it.

Discussion Questions

1. Opening question: When you hear the word "dating," what emotions come up? Excitement? Anxiety? Exhaustion? Hopelessness? [Allow time for honest sharing; this sets the tone]

2. What messages — from church, family, or culture — have shaped how you think about dating? Which of those messages have been helpful? Which might be holding you back?

3. Dr. Cloud challenges the idea that God will simply "bring the right person" without any effort on our part. How do you respond to that? Does it feel freeing, challenging, or uncomfortable?

4. If dating is meant to be a "learning and growing" journey rather than a hunt for "the one," how would that change how you approach your next date?

5. What would it look like to treat your dating life with the same intentionality you bring to your career, your health, or your spiritual growth?

6. Where in your life have you been passive when it comes to dating? What would taking ownership look like for you specifically? [This may require some silence — it's a vulnerable question]

7. What fears come up when you think about being more active and intentional in dating?

Personal Reflection Exercise

Take 5-7 minutes to write responses to these prompts:

The Ownership Audit

1. On a scale of 1-10, how intentionally have I been approaching my dating life?

   1 -------- 5 -------- 10 (Completely passive) (Fully engaged)

2. What beliefs have I held about dating that might be keeping me stuck?

3. What would it look like if I approached dating as a growth journey rather than a search for "the one"?

4. What is one area where I need to take more ownership?

Real-Life Scenario 1

Sarah is 34, has a strong faith, good friends, and a career she loves. She hasn't been on a date in two years. When friends suggest she try a dating app, she says, "I'm trusting God to bring the right person. I don't want to force it." When she's honest with herself, she admits she's afraid of rejection and the vulnerability of putting herself out there. But she's also lonely and disappointed that nothing is happening.

Discuss:

• What's valid about Sarah's perspective? What might be keeping her stuck?
• How could Sarah take ownership without abandoning her faith?
• What would you say to Sarah if she were in this group?

Practice Assignment

Between Sessions:

1. Get honest about your numbers. Count how many new, eligible people you've met in the last 30 days. Write it down. What does that number tell you?

2. Identify your passive spots. Where have you been waiting for something to happen rather than actively engaging? What's one small step you could take?

3. Reframe your goal. Instead of "find the one," try adopting this goal for the next month: "Learn something about myself, relationships, or other people." Notice how that changes your perspective.

Closing Reflection

Dating can feel like a test we're failing. But what if it's actually an invitation — to grow, to risk, to become more fully ourselves? Taking ownership doesn't mean controlling outcomes. It means showing up with intention, staying engaged with hope, and trusting that growth is always worth it, regardless of where the journey leads.

Session 2: Getting Active

Practical Steps and Facing Your Fears

Teaching Summary

If you're not meeting new people, your dating life can't change. It's that simple. Many singles live in tiny social worlds — the same coworkers, the same church friends, the same weekly routines — and wonder why nothing is happening. If your traffic pattern hasn't produced results in years, it's time to change lanes.

Dr. Cloud's challenge is simple: meet five new people a week. Not dates. Just interactions — at coffee shops, at events, at church, wherever. The goal isn't immediate romance; it's getting you out of your shell and into a bigger world. You might be surprised what surfaces when you start moving.

This is where the excuses come in. "There aren't any good ones left." "Everyone my age is already married." "Dating is impossible in my city." Here's the reality: people who say this in Chicago blame Chicago, and people in Los Angeles blame Los Angeles — for exactly opposite reasons. The problem isn't the city. It's externalizing the problem to avoid looking at our own dynamics.

Getting active also means getting over the stigma around dating services. How do you find a job today? A restaurant? A product? Online. One woman Dr. Cloud worked with met her husband through a dating service — he was number 64. She didn't give up after three bad experiences. She stayed in the process.

But here's where it gets interesting: when people start moving and meeting new people, their internal issues surface. One woman, attempting to meet someone new at a bookstore, suddenly had a panic attack. When she examined what she was thinking, it was intensely critical thoughts about her body. That moment became the doorway to growth she needed — growth that eventually led to a healthy relationship.

Getting active isn't just about tactics. It's about surfacing what's been hidden so you can deal with it. The journey is the point.

Discussion Questions

1. Opening check-in: How did the practice assignment go? What did you notice about your "numbers" or your passive spots?

2. When you imagine meeting five new people a week, what comes up? Does it feel exciting, overwhelming, impossible, or something else?

3. What are your current "traffic patterns"? Where do you spend your time? How often do those places put you in contact with new, eligible people?

4. What limiting beliefs have you held? ("There aren't any good ones." "It's impossible in my situation." "Everyone my age is taken.") What would it look like to let go of those?

5. What's your reaction to the idea of dating services or apps? Is there a stigma you're holding onto? What would it mean to get over it?

6. Have you ever had a moment — like the woman with the panic attack — where an internal issue surfaced in a dating context? What did it reveal? [Give space; this is vulnerable]

7. What would it look like to "drop your hanky" — to be more open, approachable, and engaged? What's keeping you from doing that?

Personal Reflection Exercise

Take 5-7 minutes to complete this:

The Traffic Pattern Audit

List the places and activities that make up your typical week:

Now ask:

• Looking at this honestly, is my current traffic pattern likely to produce new connections?
• What's one new place, group, or activity I could add?
• What's stopping me?

Real-Life Scenario 2

Marcus is 29 and hasn't dated much since college. He goes to work, comes home, plays video games with the same online friends, and goes to a small group at church where everyone is married. He's frustrated that he hasn't met anyone, but when friends suggest he try a new activity or join a singles group, he says, "That stuff feels forced. If it's meant to happen, it'll happen naturally."

Discuss:

• What would you say is actually going on with Marcus?
• What's the difference between something happening "naturally" and waiting passively?
• What would be a realistic first step for someone in Marcus's situation?

Real-Life Scenario 3

Jen has been on about fifteen first dates in the last year through a dating app. None of them went anywhere. She's about to delete the app and give up. "I've tried everything," she says. "It just doesn't work for me."

Discuss:

• Is fifteen first dates "trying everything"? What perspective might help Jen?
• What questions would you want to ask Jen about what's happening on those dates?
• How could Jen stay in the process without burning out?

Practice Assignment

Between Sessions:

1. Change one traffic pattern. This week, go somewhere new or try something different — a new church service, a class, a meetup, an event. Your goal isn't to find a date; it's to be in a different environment.

2. Practice five interactions. Aim to have five brief conversations with new people this week. It can be as simple as asking someone what they're reading or commenting on something in line. You're practicing engagement, not hunting for romance.

3. Notice your internal world. When you're in social situations, what thoughts run through your head? Critical voices? Anxiety? Assumptions about others? Write down what you notice.

Closing Reflection

Getting active isn't just about tactics — it's about availability. It's saying yes to life, yes to possibility, yes to the discomfort of growth. You don't have to do this perfectly. You just have to keep moving.

Session 3: Growing Yourself

Internal Work for External Results

Teaching Summary

Here's the uncomfortable truth: most of the time, good people end up with not-so-good people because of the good people's issues. Our dysfunction seeks water at its own level. If you have no boundaries, you'll probably attract a controller. If you're a fixer, you need a problem to fix, so you'll fall for one. If you can't be vulnerable, you'll end up with someone who can't respond to needs — and then wonder why they're so detached.

This is why personal growth is so essential. Becoming the kind of person who can attract, recognize, and sustain a healthy relationship is not optional. It's the work.

Dr. Cloud identifies four key developmental areas:

Attachment and Vulnerability: Can you be emotionally present? Can you express vulnerable feelings and receive someone else's? If you're emotionally detached, you'll match with someone who is too.

Boundaries: Are you controllable? Do you say yes when you mean no? Can you hear the word no without falling apart? If you can't set boundaries, you'll find someone who steamrolls them.

Perfectionism and Realness: Do you feel like you have to be perfect? Are you always performing? Can you laugh at your own failures? The sexiest connection happens when people are real with each other. If you can't take off the mask, you'll never experience true intimacy.

Equality and Adulthood: Do you show up as an equal, or do you put yourself in a child position, trying to please like your date is the judge? Healthy relationships are between two adults — not a parent and a child.

Beyond these areas, pay attention to your patterns. Many people go on "autopilot" the moment they start dating someone — abandoning their friends, giving up their opinions, losing themselves. Know your patterns, and commit to driving instead of letting the autopilot take over.

Discussion Questions

1. Opening check-in: What did you notice about your internal world during social interactions this week? Any surprising thoughts or feelings surface?

2. Of the four developmental areas (attachment, boundaries, perfectionism, equality), which one resonates most with you? Where do you see yourself needing growth?

3. When you think about your past relationships or dating experiences, do you see any patterns? The same kind of person? The same way things end?

4. Dr. Cloud says, "Our dysfunction seeks water at its own level." What does that mean to you? How have you seen that play out?

5. What does it look like to "be yourself from the beginning" in dating? What gets in the way of showing up as your true self? [Allow space — this is hard]

6. What's one area of personal growth that you sense is connected to your dating life? What would it look like to work on that?

7. If your closest friends were asked, "What does this person need to work on for their dating life to change?" — what do you think they'd say?

Personal Reflection Exercise

Take 5-7 minutes for this honest self-assessment:

The Four Areas Inventory

Rate yourself 1-5 on each area (1 = significant struggle, 5 = strength):

Attachment and Vulnerability

• I can express my needs and feelings honestly: ___
• I can be present with someone else's vulnerability: ___
• I let people see the real me: ___

Boundaries

• I can say no without excessive guilt: ___
• I can hear no without falling apart: ___
• I don't try to control others: ___

Perfectionism and Realness

• I can laugh at my mistakes: ___
• I don't feel like I have to perform to be loved: ___
• I can show up without "having it all together": ___

Equality and Adulthood

• I show up as an equal in relationships: ___
• I don't need others' approval to have my own opinions: ___
• I pursue my own interests, not just others': ___

What this tells me:

Real-Life Scenario 4

David is 38 and has been married once before. The marriage ended after three years. His ex said he was "never really there" — emotionally unavailable, buried in work, unable to talk about feelings. Now David is dating again, but he finds himself making the same choices. He's attracted to women who seem "low maintenance" and "easy to be around" — which usually means they don't ask much of him emotionally. He's starting to wonder if the problem isn't the women.

Discuss:

• What developmental area seems most relevant to David's situation?
• Why might David be drawn to "low maintenance" women?
• What growth work might David need to do before dating leads somewhere healthy?

Real-Life Scenario 5

Lisa is 31 and describes herself as "a giver." She loves taking care of people. But in every relationship, she eventually feels resentful and exhausted. She gives and gives, and the men she dates seem happy to receive — but they never step up. She wonders why she keeps attracting "takers."

Discuss:

• What might Lisa's pattern reveal about her own issues?
• How do boundaries connect to Lisa's situation?
• What would healthy change look like for Lisa?

Practice Assignment

Going Forward:

1. Name your pattern. Based on this session and your own reflection, identify one recurring pattern in your dating life — a type you're drawn to, a way you lose yourself, a moment where things typically go wrong.

2. Plan one growth step. What's one concrete thing you could do to address your pattern or grow in one of the four areas? (This might be reading a book, talking to a counselor, having a conversation with a friend, or practicing a new behavior.)

3. Stay in community. Dating shouldn't be done in a vacuum. Commit to keeping your team — these friends, a mentor, a counselor — in the loop as you navigate dating. Let them be your "dating eyeballs."

Closing Reflection

The work of becoming is never wasted. Every bit of growth you do — in your ability to connect, to set boundaries, to be real, to show up as a whole adult — makes you more capable of the relationship you're hoping for. And it makes your life better right now, regardless of where dating leads.

You don't have to be finished growing to start dating well. You just have to be in the process, aware of your patterns, and willing to do the work. That's what healthy people do. That's what you can do.

Closing Group Ritual (Optional)

If this is your final session, consider closing with:

• Each person sharing one thing they're taking away from this series
• One commitment they're making for their dating life
• A moment of silence or brief prayer for each person's journey

Note: If anyone in the group is dealing with significant anxiety, trauma, or patterns they can't seem to break, professional counseling can be a powerful next step. There's no shame in getting help — it's one of the bravest things you can do.