Is There a Guide for Midlife Holidays? Asking for Me.
I thought dating would simplify as an empty nester. Instead, it’s brought new challenges: how do I juggle my kids, boyfriend, and ex during the holidays?
A few years ago, my ex and I, long broken up, hosted Thanksgiving for his parents, my dad, a few friends, and our kids. It was one year post-pandemic, five years since we split, and just before my 42nd birthday.
I mention one year post-pandemic because you may remember this was a time of social awkwardness that could only be made worse by the usual holiday family dynamics.
No one outright opposed Pink and I’s decision to stay in each other's lives and co-parent Nick and Faith, but the questions always came:
Is this healthy?
He’s not their dad...
What kind of impression does this leave on the kids?
What happens when one of you meets someone new? How will they feel about your relationship?
These questions, side eyes, and more have followed Pinkus and me over the years as we have kept our commitment to redefining our relationship while defining what 'family' is to us.
I’d love to recount every awkward conversation from that dinner, but in today’s climate, I’d get canceled. Honestly, I almost canceled us. It’s not hard to picture when you imagine a table full of right-leaning Midwesterners (former Catholics turned Ukrainian Orthodox), a few non-practicing liberal-leaning Jewish folks, a gay middle-aged man in the arts, and Gen Z college aged kids airing their social views. My ex and I held court at the center of the table like Switzerland. Oh, and half the table was hard of hearing, which, honestly, was a blessing.
At one point, I found myself in a too-narrow hallway with my dad, who glanced at my hair and said, “Going gray, huh?”
“Yeah, Dad. Just seeing what’s going on with it.”
“What are you now? Forty-one? Forty-two?”
“Almost 42.”
“Well, may as well. You’ve aged out of the dating pool, that’s for sure.”
“You’re probably right, Dad.”
I still cry laughing at that moment—not just because my dating and sex life were peaking at the time.
This year will only be the second time I've not been with my kids on Thanksgiving. The last time was in 2019. Nick had graduated high school and was away on a gap year somewhere in Baja Sur. Faith went with Pinkus to visit his family in IN.
It felt weird to be without my kids that Thanksgiving, and the weirdness only escalated when the guy I was dating suggested we get Chinese food—because Thanksgiving foods were his least favorite- he was into CrossFit & CropTops, and Carbs were terrible. He also thought Boogie Nights would be the perfect holiday movie. My best friend came over, which should’ve made it better, but instead, it just made it stranger: the three of us, stuffed with Chinese takeout, sitting on my couch, watching coked-out porn stars spiral.
Looking back, I’m grateful my best friend was there that night. Not because she improved the vibe, but because I needed a witness to my questionable taste in men.
I knew that morning when he and I went for a run we wouldn't last. He told me a story about a time in his life when he was husband and father, and though I can't remember the details of what he said, I got the ick. The details don’t really matter anyway.
Who could love a man who doesn't love carbs?
We broke up less than two weeks later but joked for years that we said love you too soon and to avoid Chinese food with MSG it causes limp dick.
This year, my boyfriend Nate invited me to his mom's in South Carolina for Thanksgiving. At first, I dismissed it—I’m the mom; holidays happen at my place.
I thought dating would simplify as an empty nester. Instead, it’s brought new challenges: how do I juggle my kids, boyfriend, and ex during the holidays?
I know I’m not the only one who needs to know. This is midlife. Many of us are dealing with exes, kids, shared pets, some version of family- chose or not- and it can feel overwhelming. Is there a guide for this?
Has Gwyneth given us more beyond consciously uncoupling? How has she integrated Brad with her young adult kids? Although, he came into the picture while they still lived at home. Do we know if they are having dinner with Chris? Is his girlfriend there?
The truth is, midlife isn’t about “baggage” in the way people like to label it. Although, I do have really fucking nice Rimowa luggage that is covered with stickers that I've collected along the way with my travels. Cute reminders of specific destinations or experiences that captured a portion of my journey. That feels closer to how I see life now.
For years, I’ve imagined a future where my ex and I, our partners, the kids, and their partners all sit at one table together. People say I’m delusional, but I’m not so sure.
That Thanksgiving in 2021 was worth every awkward moment just to hear our parents acknowledge the friendship Pinkus and I have built— something that keeps us all connected.
Which is what I should focus on; I don’t have to force things or figure it all out ahead of time.
Life has a way of unfolding exactly as it should.
Like this year: It just so happened my kids decided not to come home for the holidays. I’m in South Carolina with Nate’s family now feeling grateful for the unexpected ways it all comes together.
And Dad? Turns out, I haven’t aged out of anything.
If you're enjoying the content and feel compelled to support this newsletter, there are a couple of ways you can help out.
You can upgrade to a paid membership, or if you'd prefer a one-time contribution, feel free to send me a donation via PayPal or Venmo.
Every bit of support is truly appreciated and helps me continue to bring you the content you love.
Thank you for being here and for your support—whether it's financial or simply through being part of this community. 🧶
RELATED POSTS 👇
Whenever it begins to wane, which happens often, you restore my faith in Gen X, I'll have you know that, Ashley. Hopefully you enjoyed your Thanksgiving.