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When Valentine’s Day Hurts More Than It Heals

Valentine’s Day can be one of those icky milestones that sneaks up on you during or after divorce.

It’s everywhere: ads, flowers, prix fixe dinners, social media posts declaring eternal love. And when your life doesn’t look anything like that, the day can feel less like a celebration and more like a spotlight on what’s been lost, what didn’t work, or what you endured far longer than you ever planned.

If Valentine’s Day hurts more than it heals this year, nothing is wrong with you.

For many women, especially those navigating divorce later in life, this holiday hasn’t felt good for years. Long before the separation or legal process began, Valentine’s Day may have already been marked by disappointment, loneliness, or unmet expectations. Divorce doesn’t create those feelings; it simply removes the illusion that things were fine.

The Weight of Milestones During Divorce

Divorce is full of emotional landmines disguised as calendar dates. Anniversaries. Birthdays. Holidays. Firsts and lasts you didn’t ask for.

Valentine’s Day often lands differently because it’s supposed to be about love, but divorce forces you to confront the reality that love, as it existed in your marriage, changed or disappeared. That realization can feel heavy, even if you know the divorce is necessary or long overdue.

You can grieve the relationship and still feel relieved it’s over.
You can feel lonely and empowered at the same time.
You can opt out of Valentine’s Day without opting out of your future.

Holding these contradictions is part of the work.

You Don’t Have to Participate

Let’s say this clearly: you do not owe Valentine’s Day your participation.

You don’t have to go out.
You don’t have to post anything.
You don’t have to celebrate love in a way that feels performative, painful, or exhausting.

Choosing not to engage isn’t bitterness; it’s discernment.

For some women, the most loving thing they can do on Valentine’s Day is to treat it like any other day. Or even intentionally make it quieter. Simpler. Kinder.

That is not avoidance. That is self-respect.

Reframing Valentine’s Day as Permission

Instead of asking, How should I celebrate Valentine’s Day? try asking:

What would feel supportive to me right now?

This isn’t about grand gestures or reinventing your life overnight. It’s about giving yourself permission to care for yourself in a way that feels honest.

Self-care doesn’t need to be elaborate to be meaningful.

It might look like:

  • Canceling plans without guilt
  • Ordering the meal you actually want
  • Taking a walk without your phone
  • Scheduling a massage or therapy session
  • Spending time with someone who truly sees you
  • Going to bed early

Or it might be something slightly bigger, a short trip, a personal purchase you’ve delayed, or creating space to reflect on what you want next.

What matters isn’t the size of the gesture. It’s the intention behind it.

Small Rituals Can Become Something More

One of the unexpected gifts of this season, painful as it can be, is the opportunity to notice what actually supports you.

A small choice you make this Valentine’s Day could quietly turn into a ritual:

  • A weekly practice that grounds you
  • A boundary that helps protect your energy
  • A habit that reminds you of your own resilience

These rituals don’t erase the grief, but they can help steady you through it. Over time, they may become part of how you begin to rebuild, both emotionally and practically.

As you start listening to yourself again, a sense of trust can gradually follow.

Loving Yourself Is Not a Cliché, It’s a Foundation

Self-love during divorce isn’t about pretending everything is fine.

It’s about:

  • Honoring your emotional reality
  • Making decisions that are thoughtful about future you
  • Creating steadiness in the middle of uncertainty

This includes caring for your finances, your boundaries, and your longer-term sense of security, because peace doesn’t come from romance alone. It often comes from clarity and understanding.

Valentine’s Day can be a reminder that love doesn’t have to come from outside of you to be real or meaningful.

A Gentle Invitation

If Valentine’s Day feels heavy, let it be heavy. If the day feels quiet, let it be quiet.

And if you find even one small way to care for yourself, hold onto that.

Healing rarely happens in grand moments. It often happens in small, intentional choices that can support a growing sense of confidence, stability, and trust in yourself over time.

If part of caring for yourself right now includes wanting more information about your finances, your options, or what comes next, we’re here.

A Clarity First™ conversation is a simple, supportive starting point. It’s a chance to pause, ask real questions, and better understand your situation and possible next steps.

You don’t have to have everything figured out to take this step.

Schedule your Clarity First™ conversation when you’re ready.

This material is provided for informational and educational purposes only and is not intended as financial, legal, or therapeutic advice. References to services or conversations are introductory in nature and do not constitute personalized investment advice. Investment advisory services are offered exclusively through Keating Financial Advisory Services (KFAS) pursuant to a written advisory agreement. Please refer to KFAS’s Form ADV Part 2A for additional information. Clarity First™ is a proprietary process developed and trademarked by Purposeful Wealth Advisors®, used under Keating Financial Advisory Services, Inc. This process is not registered with the U.S. Patent and Trademark Office. Use of this process does not imply any guarantee of results and should not be interpreted as an endorsement by any regulatory authority.

Beth Kraszewski recipient of