I’m feeling stuck and could really use some perspective. I’ve been with my girlfriend for about seven years—the same amount of time I’ve been divorced. She’s incredible. We’ve grown together, supported each other, and built a beautiful life. She’s ready for marriage, and part of me is too. But there’s this lingering fear I can’t shake.
After my divorce, I started a company that took off in ways I never imagined. With that success came a fear of losing it all. I’ve seen how messy breakups can get—mine was rough, and my parents are still tied up in financial battles years later. That history haunts me.
It’s not that I don’t trust my girlfriend. She’s been my rock. But I’ve worked so hard to build something from nothing, and the idea of losing it—again—is terrifying. I’ve looked into prenups, but even those seem uncertain.
I love her. I want a future with her—traveling, making memories, sharing everything. But I’m torn between protecting what I’ve built and fully opening up to the next chapter.
How do I move past this fear? Is it possible to protect what I’ve created without closing myself off to love?
You’ve been through hell. Divorce. Building a company from the ground up. Watching your parents locked in financial warfare. You’ve earned the life you have now—every late night, every risk, every decision. So when you say you’re scared to lose it, I get it. That fear isn’t irrational. It’s earned too.
But here’s the hard truth: You can’t logic your way into safety in relationships.
You’re trying to use spreadsheets to manage something that lives in the heart. You’re trying to protect yourself with contracts and what-ifs when what you’re really asking is, Can I trust again? Can I bet on someone—on us—without losing myself?
You can have a prenup. That’s fine. Smart, even. But don’t confuse legal protection with emotional safety. A prenup won’t heal the part of you that’s still bracing for impact. That healing—that work—is yours. And you won’t find it by standing still.
You said you love this woman. You dream of a future with her. So here’s the question: Are you willing to love her with your whole heart, even if it means risking it breaking again? Because that’s the only kind of love that works. That’s the only kind that lasts.
You’re not stuck between fear and love. You’re standing at the edge of something sacred, trying to decide if you’ll bring your whole self to the table.
The goal isn’t to make fear disappear. The goal is to stop letting fear be the loudest voice in the room.
So do the work. Talk to a counselor. Dig into those old wounds. Let your girlfriend see your fear instead of letting it drive your decisions behind the scenes.
And then, if you still want to marry her? Do it with your eyes wide open and both feet in.