The First Holidays, Birthdays, and Milestones Without Them: Reflections From a Grief Therapist After Her Mom’s 15-Year Death Anniversary

Me, my mom and my brother at the beach in the 90s.

Grief therapy is not one-size-fits-all, but there’s a general understanding among clinicians and those who have lived it that the first year after losing someone is especially hard. That doesn’t mean the years that follow are easy. In fact, the weight of grief tends to shift rather than disappear. But that first year is full of “firsts”: the first holidays, birthdays, milestones, each one a reminder that life is moving forward without someone you didn’t imagine living without.

In addiction recovery, there’s a commonly shared guideline: don’t start anything major such as big moves, new relationships, or major life decisions in the first year of sobriety. It’s about giving yourself the space to stabilize and adjust to a new normal. In many ways, the first year of grief calls for the same kind of spaciousness and gentleness. Everything is new in a painful way.

Clients often tell me they can anticipate certain days will be difficult; perhaps their parent always made a big deal out of Halloween or decorated the house for Valentine’s Day with sweet little notes. Maybe birthdays were a big production, or Father’s Day meant grilling in the backyard. These anticipated grief days are hard enough, but they’re often accompanied by a second layer of pain: feeling like others around you have moved on, or worse, don’t realize the day holds weight for you.

But often it’s the unmarked days that surprise you most. A song in an Uber. A stranger’s cologne that matches theirs. A rerun of a movie they loved. The grief floods in, seemingly out of nowhere, sometimes with more intensity than the “expected” grief days. And often, the anticipation is worse than the day itself. You brace for their birthday, their death anniversary, and then find yourself numbed out or distracted. Then weeks later, a mundane moment knocks the wind out of you.

At the time of this writing at the end of July 2025, this week marks 15 years since my mom died. Even typing that feels surreal. In the beginning, I couldn’t imagine what this far out would feel like. My relationship with her was complicated, especially in the final years. It’s not that I couldn’t picture a life without her – it’s that I couldn’t imagine how I’d carry all of the conflicting feelings over time.

In some ways, my life has been simpler without the stress of worrying about her mental health or the unpredictability that came with it. But grief isn’t always about missing someone as they were, it’s also about the loss of what could have been. I often wonder who she might have become if she’d had more support, or if we could’ve found our way back to each other as I aged into adulthood and parenthood. Would she have cracked open? Would I have understood her differently? These questions don’t have answers. But I hold them, and I let them inform how I show up now, as a parent, as a therapist, as someone who knows how fragile and fleeting this all is.

Some years I nearly forget the date of her death until I see it on my calendar. It’s buried in the haze of late July, a time when life feels busy with heat and motion. But I always remember her birthday: November 1, which happens to be Día de los Muertos. That feels morbidly fitting. I try to mark it in small ways. I light a yahrzeit candle, I play her favorite Fleetwood Mack and Madonna albums. I think about who she was, and who she wasn’t, and what I carry forward from both.

Whether it’s your first year without someone or your fifteenth, grief has a way of resurfacing. It evolves, hides, resurfaces again. There’s no linear timeline. You don’t have to feel a certain way by a certain date. And you certainly don’t have to navigate it alone.

Talking to a therapist can be helpful, especially during that first year. There’s comfort in having someone who can bear witness to your pain without trying to fix it or rush it. A therapist can help you prepare for upcoming milestones, identify what might feel supportive, and offer tools for making meaning from your grief. But even if it’s been many years, therapy can still be a space to revisit these feelings as they shift and evolve.

Grief changes with you, but it doesn’t go away. And in a strange way, that’s a testament to love. You grieve because you loved, even if the relationship was imperfect or complicated. Especially then. If you're bracing for a first birthday, a holiday, or just a random Tuesday that now feels hollow, you're not alone. Light a candle. Tell a story. Take a break. Call a friend. Or don’t. There’s no right way to do this.

Natalie Greenberg, LCSW, is a dedicated grief therapist based in New York City, specializing in helping young adults navigate the complexities of loss. After experiencing the profound impact of her mother's death by suicide at 23, Natalie found healing through therapy and support groups, inspiring her to guide others through their unique grief journeys. She earned her Master's in Social Work from New York University and holds a post-master's certificate in Cognitive Behavioral Therapy. With over a decade of professional experience, including roles at Bellevue Hospital's Psychiatric Emergency Room, Mount Sinai Hospital's leadership team and New York University’s Student Health Center, Natalie brings a wealth of knowledge, empathy and humor to her practice. She currently offers virtual therapy sessions, providing accessible support to clients throughout New York.