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It's the Most Difficult Time of the Year: 7 Tips for Supporting Loved Ones During the Holidays

Posted by Kellyn Shoecraft on

Chances are that you know someone who has had a very difficult 2019.

Maybe they lost a friend or family member, maybe someone they love is physically here but is suffering from dementia, substance use disorder, or end-stage illness. Maybe they had serious trouble at work, experienced a breakup, or are struggling with infertility.

The holidays are memory markers. They’re a definitive moment that longs for comparison. This is the time of year that we remember holidays past, and that is part of what makes them so painful. Add to that the fact that we get lots of social cues about happiness, family and togetherness — reminders of what we no longer or never had.

Finally, why are there so many gosh-darn holidays in a very short period? Annoyingly, they’re all clustered near the end of the calendar year which is also a natural time of reflection. The holiday season is, in essence, a quadruple whammy.

Ifyou know someone who is struggling this year, there are things you can do for your friends and loved ones to help make this season even slightly more manageable. These are not and don’t have to be grand gestures. They are seemingly small choices that mean a lot.

Here we go…

1. Do Something Unholidayish

Especially when it’s the first holiday after a major loss, it is so helpful to do something new, so that there is no point of comparison.

2. Call and let them steer the conversation

3. Honor Their Person


There are many ways to do this. Give a toast, light a candle, or tell stories and share memories. The bereaved love when others remember their people.

4. Be Mindful with your Holiday Card

I have never sent a holiday card, but I imagine it’s not easy. I know that many of you have lots of people on your distribution list, and it can be a bit of an assembly line-like job to get them labeled, stamped and mailed.

Be sure to add a personal note to let the person know that you remember what has happened to them this year and that you understand how difficult the holidays can be.

It can feel like a personal assault to get a card that says “Joy to the world!” in gold foil below beautiful professionally snapped and curated photos of a nuclear family when you’re struggling and missing someone (even when that’s not the intention). Adding a handwritten ‘sending love and remembering Dennis this holiday season’ can make all the difference.

5. Never Hesitate to Invite (with a caveat)

Don’t hesitate to extend an invitation, even if they are of a different religious background, or you don’t consider each other to be best friends. There are a few things to keep in mind with your invitation:

  • If you never hear from them, it doesn’t mean that they’re not grateful for being asked.
  • They might say they are coming and then never show up. They may arrive and leave after a few minutes. This is ok and you shouldn’t take it personally.
  • Ask them if they’d like details so they can prepare themselves. You could say “we’re having a New Year’s Day brunch with about 20 people. It will be a mix of friends with a few family members. My Aunt Irene will be there and she usually drinks too much and talks about politics, but otherwise, the crowd is very low key.” It helps people when they know what to expect.
  • Don’t pressure them to come and avoid advising them on what they should or shouldn’t be doing* (e.g., never say “Your mom would want you to get out and have fun,” or “You shouldn’t be alone that day.”).

*I am laughing to myself because I am giving you advice on what you should and shouldn’t be doing 😂

6. Never Underestimate the Power of a Text

7. Choose Holiday Gifts Wisely

This year we've launched our Hapless Holiday boxes — so if you are looking for a sensitive way to support someone this season, we are here to help. 

What have people done for you that’s helped during the holidays? Any other tips? Please share below.

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