Wedding Season: How to Celebrate the ‘Both/And’ Moment

Wedding season is here. It’s that stretch of spring through early fall when weekends fill with bridal showers, outdoor ceremonies, cocktail receptions, and endless Instagram moments. For some, this time of year overflows with joy. It could be a daughter’s wedding, a favorite niece walking down the aisle, a grandchild beginning a new chapter. But for others of us, this season can bring an emotional undercurrent that’s harder to share.

You might be the woman whose adult children say they’ll never marry. Or maybe you never had children and feel left out of all the “mother of the bride” conversations. Maybe you’re no longer married and it’s still raw. There are thousands of reasons why wedding season can feel less than joyful, and where each new invitation feels like a sucker punch.

The “both/and” way to navigate wedding season

No matter which side of the wedding season fence you may be on, there’s a way to both celebrate and show generosity of spirit to those who may not be. If you’re in the less-than-celebratory camp, for whatever reason, there’s also a way to celebrate and self-fortify, using “both/and” thinking. But first, let’s explore the myriad ways a wedding can leave us feeling bereft.

Understanding the emotional landscape of wedding season

We often associate weddings with pure joy, but behind the scenes, emotions can be complex. Envy, grief, loneliness, regret, and even anger can show themselves. When these feelings rise, many of us feel ashamed or guilty for not being “happy enough” or “supportive enough.”

But wedding season, like so many life events, isn’t a monolithic experience. For some, it’s a delightful whirlwind of dress shopping, gift registries, and joyful reunions. For others, it can be a stark reminder of paths not taken, loved ones lost, or dreams unfulfilled. We might as well acknowledge this spectrum of emotions, both in ourselves and in others. It’s life.

You’re not the only one

Many of us, especially in midlife, experience a disconnect from what “milestones” are supposed to look like. Society says children should grow up, marry, and start families. But life doesn’t always follow that script.

And if you’re single, divorced, child-free, suffering the loss of a child, or estranged from your family, the deluge of save-the-dates can feel like emotional salt in an old wound.

I never had children. Where do I fit in this wedding season?

Wedding season can make women without children feel invisible, as if they missed the “main event” of life. There’s a strange cultural void for those without kids, during these very public celebrations.

Embrace “both/and” thinking during wedding season

You can be both happy for your friend’s daughter and heartbroken about your own situation. You can smile at a wedding toast and still feel a pang of sadness. Feelings are not either/or — they are wide, deep, and often contradictory.

“Both/and thinking” is the alternative to the either/or way of thinking. Instead of looking at any tough decision as one side or the other, work at breaking down the barrier between the two. You’ll find this often leads to a more satisfying conclusion. The two can coexist in nearly any situation.

This post is about learning to use “both/and” thinking to navigate any situation that leaves you feeling left-out, alone, not seen, or misunderstood. And it goes beyond just wedding season.

When you’re invited to a wedding that hurts

Let’s explore how to embrace this time of year, whether you’re radiating happiness or carrying a quiet sadness. Also, how to gracefully decline an invitation, and how to extend genuine empathy to others, no matter where they are on their journey. This would be putting the Both/And Theory into practice.

When your heart aches: Finding solace and self-care

Yes, weddings are joyous celebrations. But it’s equally valid if wedding season brings you a sense of melancholy. Perhaps you’re single and longing for a partner, widowed and missing your beloved, divorced and reflecting on what was, or simply feeling a general sense of loneliness. Pretending your feelings don’t exist, or buying them beneath false-joy really isn’t fair to you.

When attending feels impossible: Graceful declines

Sometimes, despite your best intentions, the thought of attending a wedding feels genuinely overwhelming. The timing of the date may already be an extremely difficult date for you. When this happens, all our grief, sadness, and pain comes up against this very ‘joyful’ moment. This a recipe for breakdown.

If this is the case you, it’s okay to say ‘no.’ Your well-being is as important as sharing joy with the couple. And a thoughtful decline is always better than an overly fueled presence.

Your inner dialogue: Navigating grief in wedding season

When faced with an invitation that triggers deep emotional pain, our immediate impulse might be to retreat. This is a natural defense mechanism. Your inner dialogue might go something like this:

• “How can I possibly go? Seeing them so happy will just remind me of what I’ve lost.”
• “It’s not fair. My child should be here, experiencing this.”
• “I’ll just bring down the mood with my sadness.”
• “I don’t have the emotional energy for this.”
• “Will I be able to hold it together?”

These thoughts are valid. You’re not being selfish; you’re a human being grappling with the complexities of life. The “talking yourself through” isn’t about suppressing these feelings, but rather about acknowledging them fully. Then, gently, challenging them. It’s about creating a space for both your pain and the possibility of a different, perhaps more healing, response.

Reframe your inner dialogue:

1. Acknowledge Your Pain: “Yes, this hurts. It’s incredibly painful to think about my child/husband/partner not being here for this moment. It’s okay to feel this sadness, this anger, this unfairness.” Don’t judge these feelings. They are a natural part of grief.
2. Identify Your Fear: What’s the deepest fear you have about attending? Is it the fear of breaking down? The fear of feeling utterly alone in a crowd? The fear of having your grief misunderstood? Pinpointing the fear can help you address it more directly.
3. Consider the “What If”: What if you don’t go? While understandable, not going tends to lead to retreating further info isolation. What if you do go? What might that look like?
4. Shift Perspective: This is the hardest part. While your loved one isn’t physically present, their memory, their spirit, and their connection to this group remains. Could attending be a way to honor that connection?
5. Set Realistic Expectations: You don’t need to be the life of the party. You don’t need to mask your grief entirely. Your goal isn’t to be “over it,” but to engage in a way that feels manageable and perhaps, even a little bit healing.
6. Find Your “Why”: Why might you consider going, beyond obligation? Is it to support the couple? To honor these friendships? To show up for life, even when it’s hard? To remind yourself that joy can still exist, even alongside sorrow? This is “both/and” thinking.

Extending empathy: Being there for others this wedding season

If you find yourself on the ‘joyful’ side of the fence, you have the opportunity to make the day just a bit more joyful for a friend or acquaintance. Work to think of things from their perspective. As the saying goes, “We never truly know another’s pain.”

How do you do this?

• Listen More Than You Talk: If someone expresses feelings of sadness or loneliness related to wedding season, truly listen without interrupting or trying to “fix” them. Sometimes, all a person needs is to feel heard.
• Validate Their Feelings: Instead of offering platitudes like, “Oh, you’ll find someone,” or “Just focus on the positive,” acknowledge their emotions. “It sounds like this time of year is a bit difficult for you,” or “I can understand why you might feel that way,” are far more empathetic responses.
• Choose your words carefully: Anyone who’s lost a child has had to endure a person’s comparison of the loss of their 95-year-old grandparent, or worse yet, their beloved pet, and the words, “I know exactly how you are feeling.” Anyone who has lost a child AND a beloved pet can tell you the two events are not comparable.
• Don’t Minimize Their Experience: Never dismiss someone’s feelings by saying things like, “It’s just a wedding,” or “You shouldn’t feel that way.”
• Offer Practical Support (If Appropriate): If you sense someone is struggling, a simple offer of practical support can mean the world. “Would you like to grab coffee sometime next week?”
• Be Mindful of Bragging: While it’s wonderful to share your joy, be mindful of how you express it, especially around those who might be feeling vulnerable. There’s a difference between sharing happiness and inadvertently causing more pain to others.
• Avoid Comparison Traps: Don’t compare someone’s situation to your own or to others. Every individual’s journey is unique, and comparisons rarely foster empathy.
• Respect Their Choices: If someone chooses to decline a wedding invitation, respect their decision without judgment or pressure.
• Remember the Nuances of Happiness: Recognize that even those who appear outwardly joyful may have their own private struggles. Everyone carries a story, and often, what we see on the surface isn’t the whole picture.
• Cultivate a Culture of Kindness: In all your interactions, strive to be kind, compassionate, and understanding. The power of true empathy is greatly underestimated. Be on the side of having it. One small act of kindness can be the spark that lights a thousand others.

Choose your words carefully

It’s truly understandable that for some, wedding season can open up old wounds, bringing a poignant mix of joy for others and personal sorrow. When you’ve experienced a profound loss, like that of a child, the sight of young love blossoming can be incredibly bittersweet, even painful.

You might find yourself grappling with intense emotions as your child’s friends, who you’ve watched grow, now embark on their own marital journeys. The idea of “talking yourself through” these difficult feelings and then choosing to go forth with a generosity of spirit might seem daunting, if not impossible. Yet, there are profound, if sometimes subtle, benefits to be found, not just for others, but for your own healing process.

The power of generosity of spirit: Beyond obligation

Generosity of spirit, in this context, is not about pretending you’re fine, or that the person you’re interacting with is fine. It’s about a conscious decision to extend warmth, kindness, and genuine well wishes, even when your heart is heavy. It can be a profound act of courage and an active affirmation of life for a suffering person.

The transformative power of generosity of spirit

Generosity of spirit is an inner disposition, an attitude, and a way of being that permeates all your interactions. It’s an open-heartedness that chooses kindness, empathy, and positive regard, even when your own heart is heavy.

It’s particularly impactful when facing challenging situations. The pain of loss is immense, and the thought of celebrating while grieving might seem impossible. However, consciously cultivating generosity of spirit in such moments can offer unexpected benefits, not just for others, but for your own healing and resilience.

Generosity of spirit vs material generosity in wedding season

• Generosity: Typically refers to the act of giving something tangible or quantifiable – money, time, possessions. It’s an action.
• Generosity of Spirit: An attitude, a mindset, and a way of being characterized by open-heartedness, kindness, empathy, non-judgment, patience, positive regard, humility, and presence. It’s about how you show up, not just what you give.
• Still, the two can absolutely live within the same circumstance. You can absolutely be both ‘generous’ and ‘generous of spirit.’

Why cultivating generosity of spirit enriches your life

Cultivating this profound trait isn’t just about being “good” for others; it’s a powerful pathway to a more fulfilling and connected life for yourself, especially as a woman in the second half of life.

Deeper and More Meaningful Connections: People are instinctively drawn to genuine warmth and kindness. When you approach others with an open heart and no hidden agenda, they feel safe and seen. This fosters deeper trust and allows for more authentic connections than superficial interactions. A generous spirit naturally melts away defensive barriers, encouraging empathy and shared vulnerability.

Enhanced Friendships: Friends with a generous spirit are the ones who show up when life is hard, offering a listening ear without judgment, celebrating your successes without envy, and supporting you through failures with compassion. These are the friendships that endure, built on mutual respect and genuine care. Conflict becomes an opportunity for understanding rather than contention, leading to healthier resolutions and stronger bonds.

Stronger Relationships Across Generations: In families, where histories can be complex and wounds deep, a generous spirit can be a powerful force for healing and reconciliation, prioritizing connection over being “right.” It fosters improved communication because people feel heard and valued, even amidst disagreements. As you navigate the second half of life, this trait leaves a lasting legacy of love, kindness, and understanding for your children, grandchildren, and all who know you.

Inner Peace and Personal Growth: Paradoxically, when you focus on extending kindness and understanding outward, you experience a profound sense of inner peace and joy. It shifts your focus away from self-preoccupation and towards connection, a fundamental human need. Choosing to attend a difficult event like a lost child’s friend’s wedding, even with a heavy heart, becomes an immense act of courage. It proves your capacity to navigate profound emotions while still engaging with life, building incredible resilience. It’s a testament that moments of beauty and connection can still exist, even alongside deep sorrow.

Cultivating generosity of spirit is a journey

Keeping these principles in mind will gradually lead to a shift, not only in how you interact with the world but how you feel inside. Generosity of spirit isn’t about achieving a state of perfection; it’s about a continuous, conscious effort to bring more kindness, understanding, and open-heartedness into every facet of your life. The richer connections, deeper friendships, and more meaningful relationships

1. Even after losing a child/partner/spouse: you know your loved ones’ friends were a significant part of their life. Attending their wedding is a way to maintain a connection to that world, to the people your loved one loved and shared experiences with.
   • Witnessing Their Journey: You saw these young people grow up alongside your child. Seeing them reach this milestone is a testament to the lives that continue, a reminder of the future your child would have shared. It can be a way to carry your child’s memory forward, as you witness the lives of those they loved. The same goes for a partner or spouse’s friends. Instead of a ‘break,’ it can mean a continuation.
   • A Living Memorial: In a subtle way, your presence becomes a living memorial. The friends know your connection, and your decision to be there speaks volumes about the love you have for their friend (your child)/partner/spouse, and for them.
2. Combating Isolation:
   • Grief Takes Many Forms: Grief can be incredibly isolating. Maybe this is your first wedding without your husband or partner by your side. It’s easy to retreat into your own world of sorrow. Attending a social event, even a challenging one, forces you to engage with the outside world, to interact, and to step, even for a short while, out of the immediate confines of your grief.
   • Receiving Support (Subtly): While you are there to offer support, your presence also allows others to offer it to you. A warm hug, a shared glance of understanding, a quiet word of remembrance – these small gestures can be incredibly comforting and remind you that your grief is seen and acknowledged.
   • An Act of Courage: Choosing to attend despite your pain is an immense act of courage. Each time you push past the comfort zone of grief, you build resilience. You prove to yourself that you are capable of navigating difficult emotions and still engaging with life.
   • Finding Moments of Joy: Even in the midst of sadness, there can be moments of genuine beauty, connection, and even joy. Witnessing pure happiness, hearing vows of love, seeing families unite – these can be reminders that joy still exists in the world, and that can be a source of quiet strength.
   • Shifting Perspective on Happiness: It’s easy, when when feeling a loss of any kind, to feel that happiness is antithetical to your pain, or that it’s something you no longer deserve. Attending a joyous event can help to recalibrate that perspective, showing that sorrow and joy can, in fact, coexist. You might find that you can feel genuine happiness for others, even as you hold your own sadness.
   • Breaking the Cycle of Avoidance: Consistently avoiding situations that trigger sadnesscan lead to a shrinking of your world. Yes, you need to take care of yourself first. But it can be empowering to face the pain, which makes it easier the next time.
   • A Sense of Agency: Deciding to go, and then managing your emotions while there, gives you a powerful sense of agency. You are not a passive victim of your grief; you are actively engaging with life, even when it’s hard.

A legacy of love and resilience this wedding season

The benefits of attending a wedding when your heart is broken or just not feeling the joy, for any reason, are not always immediate or tangible. They might come in the form of a quiet peace, a sense of connection, a strengthening of your own resilience, or the knowledge that you’ve maintained the connection with this group.

Sometimes, just reconnecting to the enduring power of love can help you reach a new place in your path. If you’re looking for a partner, this can be a positive affirmation in reaching your dream.

And your presence, exhibiting your own generosity of spirit, becomes a statement. Even in the absence of your loved one, there is still love.