It’s that time of year filled with family, friends and lots of laughs. As my children navigated to adulthood I looked for fun conversation ideas for the family gatherings scheduled over the holiday break. Our ages span from four to 89 years young. These fun conversation ideas are perfect when the conversations lull after pie.


I borrowed this fun conversation idea from Jimmy Kimmel. A few years ago Jimmy sent a camera crew around his office and asked staff members to read the last text they received from their mom.

The video is below and it is the funniest 3 1/2 minutes you may get this week. I hope it is as funny as I remember.

Okay, I lied. This next video might be the funniest video you watch this week. The other Jimmy (Fallon) had former One Direction band member, Niall Horan on as a guest last week(ask your kids who about Niall). Jimmy asked Niall to read the Christmas classic, “Twas the Night Before Christmas” using different accents every time a bell rang.

Watching Jimmy’s reaction to Niall’s accents was just as funny as Niall’s impressive skills to toggle from his native Scottish accent to a New Jersey accent. You might want to just play these videos to get the conversations started at family gatherings.

I might have to grab a copy of the “Twas the Night Before Christmas,” and get the family in on this one.

It got me thinking that I could create my own fun conversation ideas for parties and family gatherings.


I routinely save funny texts from my kids, friends and family. This text exchange was between me and my sister-in-law two years ago.

I just noticed I chose the same graphic for this year’s Christmas card!


And, you could just snap a photo of the printable for your next party or family gathering.


I did something this year we haven’t done in years. I purchased classic childhood board games. For less than $30.00 I found a few games to start some funny conversations.


Santa bought this tabletop Scrabble at Pottery Barn last month. With family coming home for the holidays Santa might do an early delivery.

I love the idea of hanging around my favorite table and laughing and accusing each other of cheating! We are a competitive bunch!


The options are limitless. Just like this casual hot cocoa bar.

Don’t strive for the perfect party and family gathering. The best gatherings are in the less than perfect details.

It is the last full week for holiday baking! Here is my go-to royal icing recipe. I watched this guy, who is married to Angela Kinsey, who played Angela Martin on the Office.

He explains the difference between icings for sugar cookie decorating! And, he is easy on the eyes.

What family fun games do you play? Please email me your favorite board games!

fun conversation starters for year round family gatherings

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  1. Lovely photos of your sweet family my friend. This is such a clever idea. I’ll definitely use some of these conversation starters. I bought a new game this year too, I picked up The Big Bang Theory Ultimate Party Game and I already have operation, Jenga and several others to choose from too. When I told my daughter I wanted to share “no tech” games she rolled her eyes, sighed and said good luck with that.
    I’m still laughing at Jimmy Fallon’s video, Love it!!!!
    Merry Christmas xo

    1. That video is hilarious! Find Jimmy Kimmel’s on youtube. It’s a few years old, just google Jimmy Kimmel and mom texts.”
      Merry Christmas, laura

  2. Sometimes I think we share the same brain! I shared conversation starters too. I saw my comment from 2019 and it made me smile , a reminder of our cherished friendship. xo

  3. Hi Laura,
    I laughed so hard at both Jimmy Kimmel (text msgs. from mom) and Jimmy Fallon with Niall Horan.
    I wish you and your family the best Thanksgiving. I’m thankful I found your blog site this past year.
    Karen B.

    1. Thank you Karen! Your comment means the world to me!

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