A Trip For 2…..But Not The Way I Planned

I didn’t plan on being a 45-year-old widow. I didn’t plan on attending fancy galas solo. I didn’t plan on bidding in a silent auction just to win a trip for two and not be able to bring the one person I always pictured traveling with.

But God? He has a funny way of showing up in places we don’t expect.

This is the story of how I—Lori Conway, your Crazy Busy Mama—ended up winning a dream trip at the Hillcrest Gala and how that trip, born from unexpected loss, is turning into a healing getaway with one of my dearest friends who is also walking through the valley of grief.

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The Gala I Almost Didn’t Go To

First off, I have to give a huge heartfelt THANK YOU to my friend Tara. She’s the one who invited me to the Hillcrest Gala in the first place.

Truthfully, I hesitated. It felt weird to get dressed up and go out to something that used to be a we event. My husband and I loved going to events like that together—cleaning up nice, sipping something sparkling, laughing across candlelit tables. And now? Just me. Alone.

But Tara nudged me. “Come for the cause,” she said. “Come for a night out.” She didn’t push hard—just gently reminded me that sometimes the first step to healing is getting out of the house.

So I went.

And I’m so glad I did.

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A Room Full of Kindness and Silent Auctions

One of the most surreal parts of walking into the Hillcrest Gala was knowing that my husband, Quintin, used to volunteer for this ministry and at times this very event.

He was the kind of man who showed up—not just for our family, but for our community. Year after year, he gave his time to Hillcrest because he believed in second chances and helping others rise.

This gala wasn’t just a date night on the calendar—it was part of our rhythm. Something we did together. Something we believed in together.

Walking in without him… it stung.

There were moments when I had to blink back tears just from recognizing faces, hearing stories, or imagining his hands busy helping behind the scenes like he always did.

But somehow, being there also made me feel closer to him.

It was like God whispered, “You’re still a part of this. He’s still a part of this.”

The Hillcrest Gala wasn’t just beautiful—it was deeply meaningful. The mission behind the event was powerful: supporting individuals and families transitioning out of homelessness. There was joy in the room, purpose, and also a sense of hope—something I haven’t always felt since losing my husband.

And then came the silent auction.

There was artwork, gift baskets, spa packages… and then I saw it:And when I won that trip in the auction? It didn’t feel like a coincidence.

 A trip for two.

My heart caught a little. Two.

That number hit me in the chest. I almost scrolled right past it. It felt like a cruel reminder. But something in me paused.

It felt like Quintin would’ve wanted this for me—a gift from the very night we would’ve shared, now becoming a chapter in my healing.

Maybe… maybe this wasn’t about what I didn’t have anymore.

Maybe it was about making room for something new.

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The Moment I Said “Yes” to Me

I placed a bid.

It felt weird—selfish even. But let me tell you something I’m learning: grief doesn’t mean you have to stop living. Grief doesn’t mean you can’t say yes to joy, to rest, to fresh air and new places.

And wouldn’t you know it? I WON.

Cue the tears. Not the “woohoo Vegas baby” kind of tears—more like the silent-in-the-bathroom kind of tears. Because the trip I just won wasn’t the trip I had dreamed of with Q.

But it was a gift.

And maybe it was exactly what I needed.

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A Different Kind of Travel Buddy

Now came the big question: who would I take?

There are people in my life who have held me through this storm—friends, family, my kids. But there was one person who came to mind almost immediately. A woman who has also known deep loss. A woman who understands the ache of walking into a room meant for two with only one set of footsteps.

She’s not just a friend. She’s a grieving sister in Christ.

We’ve laughed, cried, and asked hard questions together. We’ve prayed through panic attacks and celebrated the tiny victories of getting out of bed on dark days.

And now, we’ll sit on a plane together—two women healing out loud.

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The Gift of Grief Friendships

There’s something sacred about grieving with someone else who gets it. You don’t have to explain the silent stares. You don’t have to justify why a song at the airport makes you cry. You don’t feel pressure to “move on” or “cheer up.”

You just are. Together.

This trip will be a reset. A chance to cry, laugh, journal, pray, eat way too much food, and maybe even dip our toes in some healing waters.

Because when you’ve lost so much, you don’t need extravagant plans—you just need space to breathe again.

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Why This Story Matters (and Why I’m Sharing It)

I’m sharing this blog not just to tell you about a fun trip or say thank you to Hillcrest. I’m sharing because:

If you’re reading this and you’re deep in the trenches of loss—please hear me: it won’t always hurt this sharp.

I never thought I’d be able to smile again without guilt.

I never thought I’d board a plane again without a hand to hold.

But I’m learning that healing doesn’t mean forgetting. And joy isn’t betrayal. It’s a way of honoring the ones we’ve lost by continuing to live.

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Thank You, Tara—and the God Who Nudged Me Through You

Tara, I can’t thank you enough for inviting me to that gala. You had no idea that saying, “Hey Lori, want to come?” would end in a trip I didn’t even know my soul was desperate for.

God knew.

He used your invite to open a door. Not just to a vacation, but to freedom.

Thank you for being the kind of friend who doesn’t fix grief—but sits in it with me. You’re the kind of person who makes life feel possible again.

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To the Woman Reading This:

If you’re standing in the aftermath of heartbreak… if the world feels loud and you feel invisible… if you’re saying no to life because the one you love can’t say yes anymore—I want you to consider this:

What would it look like to say “yes” to something just for you?

Not to forget. But to heal.

Say yes to the dinner invite. Say yes to the trip. Say yes to the chance to make a new memory alongside the old ones. Say yes to feeling joy again—and not feeling guilty about it.

Here’s something we don’t talk about enough: when you’re a widow, a mom, a caregiver—you become everyone’s rock.

But who’s filling you back up?

This trip—this unexpected little miracle of an auction win—is a reminder that grieving women deserve joy.

We deserve to laugh again, rest again, and remember ourselves in the chaos of survival.

Whether it’s through travel, prayer, counseling, or coffee dates with someone who truly sees you—make space for you.

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What’s Next for This Crazy Busy Mama?

Am I scared to take this trip? Yes. Will there be tears? Probably.

But I’m also excited.

Excited to step into a new story. One filled with laughter, sunscreen, sandals, and maybe even hope.

I’ll be documenting the whole trip here on the blog and over on Instagram @crazybusymama, so be sure to follow along. Not because it’s glamorous. But because it’s real. And real is enough.

And to every grieving mama, widow, or worn-out woman reading this: you’re not alone.

Even in the silence, God is writing something beautiful.

Even in the ache, healing is on the move.

Even if you feel broken, you are still becoming.

I didn’t get to pack this bag with Q.

But I’m packing it with love, healing, and the quiet strength of two women who refuse to let grief win.

Thank you, Hillcrest Gala. Thank you, Tara. Thank you, Jesus.

This Crazy Busy Mama is going on a trip—and she’s bringing her broken heart and open hands with her.

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Let’s remind the world that healing doesn’t have to be quiet—and joy after loss is still holy.