Relationship Matters: “My girlfriend wants marriage, but I fear losing everything “

Hey,

I’m kind of stuck and hoping you can shed some light on things for me. See, I’ve been with my girlfriend for the same amount of time I’ve been divorced—about seven years. She’s amazing, truly. We’ve grown together, laughed, and supported each other through thick and thin. And here’s the thing: she’s ready for marriage, and part of me is too. But, there’s this other part, this nagging voice in the back of my head, that’s holding me back.

A bit of background might help. After my divorce, I started my own company. It took off, way more than I ever dreamed. Now, I’m sitting on a success I didn’t see coming, and with that success comes a sort of… fear. I’ve seen how ugly things can get in court (been there, done that), and my own parents are still tangled up in financial disputes that seem endless. All this has me spooked. I know what it’s like to lose everything, and the thought of going through that again terrifies me.

Now, don’t get me wrong. It’s not that I don’t trust my girlfriend. She’s been my rock, and I know she’s not out to get me or my money. It’s just… after working so hard to build something from the ground up, I’m scared to death of losing it. I’ve read up on prenups, but everyone seems to have a story about how they can fall through when you least expect it.

So here I am, loving this woman with everything I’ve got, dreaming of traveling the world with her, sharing all these amazing experiences… but I’m stuck. Stuck between wanting to leap into the future with her and being terrified of what I might lose if things don’t go as planned. I know life’s a risk, but how do you risk everything you’ve built? How do you share your life with someone without worrying about protecting the life you’ve made for yourself?

I guess what I’m asking is, how do I move past these fears? How can I make sure my future is secure without putting walls up around my heart? Is it even possible to have both?

 

First off, I want to acknowledge the weight of what you’re carrying. The fears you’re grappling with are very real and understandable, especially given your past experiences. It’s clear that you’ve put an immense amount of heart and hard work into rebuilding your life and creating something truly impressive with your company. That’s no small feat, and it’s natural to want to protect what you’ve built.

At the same time, I can hear the deep love and connection you share with your girlfriend. Seven years is a significant chunk of life to share with someone, and it sounds like you’ve cultivated a bond that’s truly special. The fact that you’re dreaming of a future with her, of sharing in life’s adventures side by side, speaks volumes.

So, how do you reconcile these two powerful forces—the desire to safeguard what you’ve created and the longing to build a life with the woman you love?

First, I think it’s important to recognize that no amount of legal paperwork can provide absolute certainty. Life is inherently unpredictable, and even the most ironclad prenup can’t guarantee a specific outcome. That said, having open, honest conversations with your girlfriend about your fears and working with a trusted legal professional to put protections in place can provide a measure of assurance. It’s about finding a balance between protecting yourself and creating a foundation of trust and commitment with your partner.

But beyond the practical considerations, I think the real work here is internal. It’s about learning to live with uncertainty and vulnerability, about taking calculated risks in the name of love and connection. Because at the end of the day, that’s what a meaningful life is all about. It’s not about hoarding wealth or shielding yourself from every potential heartbreak. It’s about showing up fully, loving deeply, and being brave enough to chase the things that matter most.

So my advice? Keep talking to your girlfriend. Keep being honest about your fears and your hopes. Consider couples counseling to help navigate these complex emotions and build an even stronger foundation. And most importantly, don’t let your fear of loss keep you from embracing the beautiful life that’s right in front of you.

You’ve already proven your resilience and your ability to rebuild after unimaginable loss. Trust in that strength. Trust in the love you’ve nurtured. And take the leap, not because you have a guarantee, but because your heart is telling you it’s worth it.

Wishing you clarity and courage,