Is My Boyfriend Holding Me Back?

Summary

Episode Summary: Is My Boyfriend Holding Me Back?

Podcast: The Ramsey Show Highlights
Host(s): Dave Ramsey, Rachel Cruze
Date: September 7, 2025
Caller: Lauren

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Brief Overview

In this episode, Dave Ramsey and Rachel Cruze take a call from Lauren, a 30-year-old woman who's achieved significant financial milestones but is concerned her long-term boyfriend is undermining her progress. Lauren seeks advice on whether to stay in the relationship or walk away, given her boyfriend's persistent financial irresponsibility and their clashing values.

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Key Discussion Points & Insights

Lauren’s Situation & Concerns

• Lauren’s Achievements:

  • Debt-free, fully funded emergency fund
  • Paid cash for a car, plans to buy a house
  • Has been following the Baby Steps for about 7 years ([00:06])

• Her Boyfriend’s Behavior:

  • 49 years old, "not very financially responsible"
  • Cleaned up past tax problems, but continues to finance (and is underwater on) vehicles
  • No significant progress during their eight-year relationship ([00:51]–[01:12])

Money Conversations in Relationships

• Attempts at Communication:

  • Lauren has repeatedly tried discussing money issues with her boyfriend

  • He typically becomes defensive or tries to minimize the problem, saying, "If I just change this one thing, this will all go away." ([02:25])

    • Lauren: “He either becomes very Defensive. Like ... if I just change this one thing, this will all go away. Or, you think I’m so bad with money and finances.”

  • Dave’s blunt interjection:

    • “Yeah, I kind of do.” ([02:43])

Deeper Issues: Respect and Compatibility

• Crux of the Problem:

  • Rachel and Dave focus on values, respect, and long-term compatibility, not just money

    • Rachel: “Do you look at him and think what a winner he is?” ([02:52])
    • Lauren admits, “No, I don’t. Yeah, I don’t at all.” ([03:11])

  • Dave reframes the conversation:

    • “Oh, it's not a matter whether he's holding you back. It's a matter of what do you want to spend your life with?” ([03:13])

• Reflection of Values:

  • Rachel: “To me, it’s not about the money...it’s the values and the patterns at which he lives his life. And when those are in conflict with ... how you live your life, that’s a really hard marriage.” ([03:20])

• Impact on Relationship:

  • Dave: “Your very presence reveals his deficits. …I often feel like his mother rather than his … partner.” ([03:44], [04:03])

The Question of Change

• Unlikelihood of Change:

  • Dave is direct: “It's been eight years...He’s not gonna change.” ([04:32])

  • Lauren echoes this concern: “That's what I was afraid you'd say.” ([04:47])

  • Dave: “When you announce this and he says, ‘oh, I'll change,’ he means it. But he still won't.” ([04:49])

• Age and Patterns:

  • Rachel points out: “He's a 50-year-old man. … You're not dealing with somebody young trying to figure it out.” ([05:03])

Practical Guidance and Emotional Support

• Book Recommendation:

  • Dave recommends Necessary Endings by Dr. Henry Cloud, stating:
    • “It will inform your intellect and soothe your emotions as you decide to walk through this.” ([05:19])

• Normalizing the Difficulty:

  • Dave encourages compassion, not cruelty:
    • “You’re not a mean person. … This is just not going to end well. I don't want to be sitting here 40 years from now. … It's hard to do in depth, close relationships with anyone you don't respect.” ([05:19]–[06:15])

The Long-Term Consequence of Inaction

• Pattern and Blame:

  • Rachel: “His response to you pushing a little bit of conflict when it goes defensive and you start getting blamed, that's going to be your relationship… Not just with money, but other things.” ([06:15])

• Final Advice:

  • Dave and Rachel gently nudge Lauren toward ending the relationship, underscoring that neither individual is likely to be happy or fulfilled if things continue as they are.

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Notable Quotes & Memorable Moments

• Dave Ramsey:

  • “Oh, it's not a matter whether he's holding you back. It's a matter of what do you want to spend your life with?” ([03:13])
  • “Your very presence reveals his deficits.” ([03:44])
  • “It's been eight years, and … He's not gonna change.” ([04:32])
  • “When you announce this and he says, ‘oh, I’ll change,’ he means it. But he still won’t.” ([04:49])

• Rachel Cruze:

  • “To me, it’s not about the money… it’s the values and the patterns at which he lives his life.” ([03:20])
  • “That's going to be your relationship… not just with money, but other things.” ([06:15])

• Lauren:

  • “I often feel like his mother rather than his partner.” ([04:03])
  • “No, I don’t [respect him]. Yeah, I don’t at all.” ([03:11])

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Key Timestamps

• Lauren shares her background: [00:06]–[01:12]
• Lauren’s question and context: [01:17]–[01:30]
• Money talk and partner reactions: [02:11]–[02:43]
• Respect, values, and relationship crossroads: [02:52]–[03:44]
• Consequences and prognosis: [04:31]–[04:49]
• Practical next steps and closure: [05:03]–[06:15]

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Episode Tone & Approach

Dave and Rachel provide clear-eyed, compassionate, and practical advice—in characteristic Ramsey Show fashion. They validate Lauren's achievements, affirm her concerns, and gently but firmly advise her to prioritize alignment in values and mutual respect over hope for unlikely change.

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Bottom Line:
Staying loyal to your values and requiring respect in a relationship is more important than enabling a partner’s financial and emotional stagnation—regardless of history or intentions for change.

Transcript

[Dave Ramsey]

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[Lauren]

So I'm 30 years old. I have been following the baby steps for a little over six years, probably about seven now. I got out of debt. I have an emergency fund. I was able to pay cash for a car last year and I've been way to go. Thank you. Thank you so much. I've been ready to start saving up for a house I'm currently renting. But I've also been in a relationship with someone for eight years. He's 49 and is not very financially responsible. And I think I need some advice on next steps to take.

[Rachel Cruze]

Dang. So your financial transformation happened while you've been dating him? Like you said, you went, you did all of this? Okay.

[Lauren]

Yes.

[Rachel Cruze]

And what.

[Dave Ramsey]

And meanwhile he. And meanwhile he did nothing?

[Lauren]

Pretty much. He cleaned up some tax problems that he'd had in the past. Good.

[Rachel Cruze]

He's now legal.

[Lauren]

Yes. But he's since financed vehicles and now he has one working vehicle and one non working vehicle and they're both financed and he's very upside down.

[Dave Ramsey]

And so exactly what is your question?

[Lauren]

Exactly? My question is, do I need to take care of myself by getting out of here or is there something else I can do to help them? You know, see the light? Quote, unquote.

[Rachel Cruze]

Well, have you guys, have you guys talked about it? Had conversations over the last eight years about money?

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[Rachel Cruze]

Well, have you guys, have you guys talked about it? Had conversations over the last eight years.

[Lauren]

About money for many, many years? Yeah.

[Rachel Cruze]

Can you raise these concerns that it makes you nervous and kind of fearful with his financial patterns? And what does he say?

[Lauren]

He basically, he either becomes very Defensive. Like, I'm. I'm doing this and I'm doing that, and if I just change this one thing, this will all go away. And. Or you think I'm so bad with money and finances.

[Dave Ramsey]

Yeah. Yeah, I kind of do.

[Lauren]

Yeah, I kind of do. I just don't know where to go from here. Is it. Is it time to, you know, face the facts?

[Rachel Cruze]

I mean, a question I always like to ask Lauren is, do you look at him and think what a winner he is? Do you?

[Lauren]

Yeah, there's.

[Dave Ramsey]

No.

[Lauren]

There's. There's. That. Yeah, that's in there. That's.

[Rachel Cruze]

Do you want to be married to that?

[Dave Ramsey]

You don't. You don't respect him, do you?

[Lauren]

No, I don't. Yeah, I don't at all.

[Dave Ramsey]

Oh, it's not a matter whether he's holding you back. It's a matter of what do you want to spend your life with?

[Lauren]

Yeah. Yeah.

[Rachel Cruze]

And I'll say this, Lauren. To me, it's not about the money. You know, a certain amount of money that he's worth or whatever. It's the values and the patterns at which he lives his life. And when those are in conflict with how the value system at which you live your life, that's a really hard marriage. To be a team and to enjoy life together. Like, you know what I mean?

[Dave Ramsey]

Like, you're gonna make him miserable.

[Rachel Cruze]

You're gonna make him miserable, and he's gonna.

[Dave Ramsey]

No. And he's gonna make you miserable. But, I mean, you need to understand that, you know, just. Just standing beside him makes him. The reflection is not good. You know? I mean, it's. That's the truth. I mean, your. Your very presence reveals his deficits. And so I often feel like his.

[Lauren]

Mother rather than his brother.

[Rachel Cruze]

Yeah. Yep. Yep. Well, because you sound like the responsible one, the one that lives in reality. You know what I mean?

[Dave Ramsey]

I think you have already made your call before you called here, hadn't you?

[Lauren]

I might have. Yep.

[Rachel Cruze]

I'm sorry, Lauren. That's hard. I mean, eight years. That's. Yeah. Do you guys live together? Are you guys gonna have to, like, separate? Okay. Yeah. So it's gonna be a big. Yeah. This is a big. A big breaking, for sure.

[Lauren]

Absolutely.

[Dave Ramsey]

And here's the other thing. It's been eight years, and this is not. And it has been discussed over and over and over and over. He's not gonna change.

[Lauren]

That's what I was afraid you'd say.

[Dave Ramsey]

So when you. When you announce this and he says, oh, I'll change, he means it. But he still won't.

[Lauren]

But he still won't. Yeah.

[Dave Ramsey]

Do you think? I mean, the pat. The pattern is ingrained. I just know.

[Rachel Cruze]

Well, Annie's a 50 year old man. Do you know what I'm saying? I'm like, it's not like you guys are both 24 year olds and he's like trying to figure out the world. I'm like, dude, you got like 12 years on me and my husband. I don't know, part of me is like, you're 50.

[Lauren]

19 years old.

[Rachel Cruze]

50.

[Dave Ramsey]

I'll tell you what I would do is I would pick up the book necessary endings by Dr. Henry Cloud. I think it will inform your intellect and soothe your emotions as you decide to walk through this. Because we're doing an emotional thing with an intellectual discussion and that's, that's a hard, you know, and then when you get into it, it's going to be emotional and because you're not a psychopath, so. And you like him, you love him, you don't want to hurt him. You're not a mean person. We're not trying to bully someone or gaslight them or something like that. It's just, you're just going, this is just not going to end well. I don't want to be sitting here 40 years from now. That's what you're saying. The trajectory on this sucks. And you just don't respect him. And it's hard to do in depth. Close relationships with anyone you don't respect.

[Rachel Cruze]

And his response to you pushing a little bit of conflict when it goes defensive and you start getting blamed, that's going to be your relationship. Not just with money, but other things. Right. That's the value system and the paradigm he lives in. And yeah, you don't want a partner like that.

[Dave Ramsey]

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