Dating After Divorce: Financial Red Flags You Shouldn’t Ignore

For a lot of my clients who are out in the dating world, I know it’s a jungle out there.

And while I wish nothing but a romantic happily ever after for anyone who is looking for it, the financial advisor in me can’t help but send those clients out with a word (or a few words) of caution when it comes to financial red flags.

If you’re dating in midlife, you’re not out there with starry-eyed optimism and zero context anymore. You’re dating with experience, responsibilities, maybe kids, maybe an ex, maybe a very hard-earned sense of financial independence you’re not willing to gamble away.

After divorce (or long-term relationships), money isn’t theoretical. You’ve seen what happens when finances are misaligned. You know how expensive starting over can be. So, if something feels “off” this time around, it’s worth paying attention.

Let’s talk about the financial and romantic red flags that tend to show up in midlife—and when walking away is the smartest move you can make.

They Avoid Money Conversations Entirely

If every attempt to talk about money is met with jokes, defensiveness, or a quick subject change, that’s not a quirk - it’s a warning sign.

Healthy relationships don’t require perfect finances, but they do require honest conversations. If someone refuses to talk about money at all, it often means they’re avoiding accountability, transparency, or both.

Why it matters: Money conversations don’t get easier with time if they’re impossible now.

Their Financial Story Keeps Changing

One minute it’s “I’m just between things,” the next it’s “I had a rough year,” then it’s “I don’t really believe in traditional money systems anyway.”

Everyone’s allowed setbacks, but inconsistent stories, missing details, or vague explanations around debt, income, or financial obligations can signal bigger trust issues.

Gut check: If you feel confused instead of informed, that’s information.

Big Financial Secrets Come Out Late

Hidden debt. A past bankruptcy you weren’t told about. A business venture gone wrong that’s still lingering.

It’s not the mistake that’s the red flag - it’s the secrecy. Trust erodes when important financial realities are revealed only after emotional investment is deep.

Reminder: Transparency early on is a sign of respect.

Divorce Debt is Still Running the Show

Many people come out of divorce carrying financial baggage: legal fees, buyouts, support obligations, or depleted savings. That alone isn’t the issue.

The red flag appears when someone refuses to acknowledge how much those past decisions still affect their present (and future).

Ask yourself: Are they being honest about the impact, or pretending it’s “all behind them” when it isn’t?

Rushing Financial Intimacy to Feel Secure

Moving in quickly to “save money.” Combining expenses early because it feels easier. Talking about buying property together before you’ve talked through debt, spending habits, or long-term goals.

After a divorce, it’s common to crave stability again, emotionally and financially. When life has felt uncertain, financial togetherness can feel like proof that things are solid this time. But sometimes what looks like commitment is really a shortcut to comfort.

Rushing financial intimacy can mask unresolved differences around money, risk, and responsibility. Shared accounts or shared leases don’t automatically create trust - they just create shared consequences.

Hard truth: Speed doesn’t equal safety. Alignment does. And alignment takes conversations, time, and a willingness to slow down, even when it feels tempting not to.

You Start Compromising Your Independence

One of the clearest midlife red flags is subtle, not dramatic. It shows up when you start bending in small ways: spending more than feels comfortable to keep the peace, postponing personal goals, or feeling guilty for wanting financial autonomy you worked hard to build.

Midlife isn’t the season to undo your stability for the sake of connection. You didn’t rebuild your life, your confidence, or your finances just to hand over control again, quietly, piece by piece.

Love should enhance your life, not destabilize it.

When Walking Away Is a Power Move

Walking away after divorce or in midlife isn’t dramatic; it’s informed. It’s the result of experience, reflection, and a clearer understanding of what you’re no longer willing to carry.

You’re not walking away because someone isn’t perfect. You’re walking away because you recognize that ignoring red flags now comes with a much higher cost than the temporary discomfort of leaving. You’ve lived the long-term consequences before—and you’re choosing differently this time.

If you’re navigating a new relationship, dating after divorce, or trying to protect the life you’ve worked hard to rebuild, you don’t have to sort through the financial questions alone.

At Life Story Financial, we help Denver women think through money decisions in real life - not just on paper. From protecting your independence to making sure a new chapter aligns with your values, we’re here to help you move forward with clarity.

Ready to talk it through? Reach out to Life Story Financial and let’s make sure your next chapter feels as good financially as it does emotionally.