It’s a challenge to craft a meaningful condolence note in the best of circumstances. But how do you acknowledge a death when the relationship between the bereaved and the deceased was difficult or even estranged?

The depth of one’s grief doesn’t necessarily equate to the quality of the relationship, so just because someone had a difficult relationship doesn’t mean they’re not hurting. It’s even possible that they’re hurting more because the opportunity for reconciliation has passed. And they’ll grieve that loss along with what might have been.

So what’s an appropriate response to this complicated loss? You can call or write a condolence note expressing your sadness at hearing the news. Even if the bereaved doesn’t want to discuss it, extend an invitation to get together for a visit, either for coffee, a meal, or a walk. Grief from this loss is complicated so if the bereaved does open up to you, a willingness to listen will be appreciated. If you’re uncertain about making a donation in memory of the deceased, you can always make a donation to a cause you feel would be meaningful to the bereaved. The reason for the donation is simple; thinking of you.

Just like any loss, your friend will need a friend. And that’s where you come in.

People express concern in finding the right words to write a truly appropriate condolence message. But it's not your mastery with words that's important; what are truly memorable are messages that come from your heart.

It's been ten years since my mother died and I'll light a candle this week to honor her memory. The anniversary of her death sparked thoughts on the condolence messages that I received that truly brought me comfort. I thought I'd share some of the qualities that made these messages special.

1. Memories are all we have left when a loved one dies and it's wonderful to hear someone else's perspective of our loved one. One friend shared: "Your mom was always so fun to speak with. Many from her generation tell the same stories over and over but your mom had so many interests and travels, I loved to visit with her."

2. It can be insightful to hear how others viewed your family member. My cousin shared: "I always thought it must have been so much fun growing up in your family. You always seemed to be such an active and involved bunch. I can only imagine what a great teacher your mom must have been because she had such a keen interest in so many things."

3. A friend made me feel better for feeling so bad. She shared: "It is always difficult to lose your mom, no matter what your age."

4. And someone from my book club who was not an intimate truly touched my heart when she referred to my mom as "Your dear mother."