sticky date cinnamon rolls

sticky date cinnamon rolls | two red bowls

sticky date cinnamon rolls | two red bowls

Hi friends! How was your Thanksgiving? We spent ours with my parents and my brother last week, in a couple of slow, wonderful days at home. It was pretty exciting — we sat around and told the same stories for the eighty-seventh time each, I woke up way earlier than you’d ever usually find me so that I could have sleepy coffees with my dad, my sole responsibilities at any given point were not overfilling the wonton wrappers (I failed) and making sure my mom got a Black Friday discount on a jewelry box from J.C. Penney, and my little brother drove me around everywhere because I’m very lazy and he’s nice and he “misses driving anyway.” So actually it was zero percent exciting. (But one hundred percent awesome.)

And now we’re back in New York! I’m always a little forlorn when I say goodbye to my family, but the good thing about this goodbye is that it’s after Thanksgiving, which means Christmas baking, which means cinnamon rolls, which means the best thing ever. And you cannot be gloomy when you have cinnamon rolls. That’s just science. Especially these sticky date cinnamon rolls, which I love more than I have possibly ever loved any squashy, warm, spiced baked good. For a long time I thought there was just one ideal of the perfect cinnamon roll, but slowly I’ve come to suspect differently — there are ones that take after brioche, with a distinct buttery richness in the dough; ones that are soft but nearly cake-like; ones with a thin, translucent sugar-sweet glaze and ones with thick, tangy, must-be-spread frosting. What I think of when I imagine my own dream cinnamon roll (or, in other words, the one I dreamed of when I was 10 and in the airport and woefully longing for a Cinnabon) is exactly how these came out — feathery-light, gooey, and barely on the right side of baked; so dangerously squishy that they yield instantly under a fork, but still more reminiscent of the very softest dinner roll than cake, with just enough gluten to have a little chew. They’re blanketed in a cream cheese frosting that’s somewhere in between the two poles of thin glaze and thick spread, pourable but in thick dollops and ribbons, not too tart but not tooth-achingly sweet.

And then there’s the date filling — as promised, the return of my much-loved dates! They’re the only thing that makes these different from the cinnamon rolls of my childhood, but now that I’ve tried them, I’m convinced dates make an even better vehicle for that warm, toasty cinnamon than brown sugar and butter. After my last post on them, I don’t know if it’s possible to wax any more lyrical about how much I love dates, but the rapture continues, and this filling is everything I love about dates encapsulated — sticky, moist, and soft, full of comforting, sweet molasses-y warmth, just like a good, plump date should be. It has all the gooey decadence of a traditional cinnamon roll filling, but with a more nuanced flavor and a bolder, more substantial texture, not to mention just a smidge more healthfulness. In my mind, this is kind of like a cross between a Christmas date cake and a classic Christmas-morning pan of cinnamon rolls — good enough for me to make on the very first day I could claim it was time for Christmas baking (and potentially way before that … I admit nothing) and then to make umpteen times more before December 25th. They’re peaceful, slow, easy baking, for a result that’s pure comfort and holiday warmth, and they remind me of all that I love about family and this cozy time of year. I really hope you enjoy them as much as I do. And if you celebrated last week, I hope you all had wonderful Thanksgivings!

sticky date cinnamon rolls | two red bowls

sticky date cinnamon rolls | two red bowls

sticky date cinnamon rolls | two red bowls

sticky date cinnamon rolls | two red bowls

sticky date cinnamon rolls | two red bowls

sticky date cinnamon rolls | two red bowls

sticky date cinnamon rolls | two red bowls

Sticky date cinnamon rolls

Yield: 8-10 cinnamon rolls, or enough for a 9-inch skillet.

If you're finding good dates hard to come by, Nuts.com will deliver them in bulk and I've always found them to be delicious when I've ordered from there. (If you want to try something other than Medjool, I love their Khadrawi and Honey dates!) And just in case you have a hankering for a full-on traditional cinnamon roll instead, see the Notes below for a standard brown sugar, butter, and cinnamon filling.

Ingredients

  • for the dough:
  • 1/4 cup (60 ml) milk (any kind will do)
  • 1 tsp active dry yeast
  • 2 cups (250 g) flour, plus more for rolling out
  • 3 tbsp (37 g) granulated sugar
  • 1/8 tsp salt
  • 1/4 cup (60 g) Greek yogurt (alternatively, use 1/2 cup buttermilk in place of the milk and Greek yogurt)
  • 1 large egg, room temperature
  • 1 large egg yolk, room temperature (if you like, use the egg white for an egg wash)
  • 1/2 tsp vanilla extract (my all-time favorite is this one, and Ashlae has it back in stock this morning!)
  • 3 tbsp (42 g or 1.5 oz) unsalted butter, melted
  • for the filling (see Notes for a traditional cinnamon filling):
  • 1 cup Medjool dates, pitted (about 8-10 dates)
  • 1 tbsp (14 g or .5 oz) unsalted butter, melted (optional)
  • 1-2 tbsp (12-25 g) brown sugar, depending on the sweetness of your dates
  • 1 tbsp cinnamon (or more or less, to taste)
  • for the icing:
  • 1/4 cup (56 g, 2 oz, or 1/2 stick) unsalted butter, softened
  • 1/4 cup (56 g or 2 oz) cream cheese, softened
  • 1 cup (125 g) powdered sugar
  • 1/2 tsp vanilla extract
  • 2 tsp (about 15 ml) maple syrup
  • 1-2 tbsp (15-30 ml) milk (any kind will do; optional)

Instructions

  1. The night before: For the dough, heat the milk in a Pyrex measuring cup or a small bowl until just warm to the touch (about 110 F or less) and sprinkle the yeast over top. Set aside for about five minutes, or until foamy on top. (See Notes if yours is having trouble foaming.) Meanwhile, whisk together the flour, sugar, and salt in a separate, large bowl.
  2. When the yeast is foamy, add the yogurt, egg, egg yolk, vanilla extract, and melted butter to the yeast-milk mixture and whisk to combine. (If you like, you can save the egg white and use it as a quick egg wash before you bake the rolls.)
  3. Add the wet ingredients to the dry, then mix with a wooden spoon or rubber spatula until all the flour is incorporated and a wet, sticky dough forms. Knead in the bowl for 5-6 minutes. The dough will be very wet -- the looser and stickier the dough is now, the fluffier and softer the rolls will be later, so don't worry if it seems gloppy, and try not to add too much flour as you knead. If kneading with your hands, you can add a bit of flour as necessary to keep from sticking, but I just kneaded it by folding it in on itself with a large rubber spatula, which did the trick just fine and kept things from getting frustrating. When the dough begins to look a bit smoother and more elastic, cover with plastic wrap or a damp cloth and place it in the refrigerator to rise overnight. (Alternatively, you can let the dough rise at room temperature for about 2 hours, or until well-doubled -- I prefer overnight to allow the flavor and gluten to develop more fully, and because a cold dough is much easier to work with, especially a delicate one like this.)
  4. The night before or the day of: For the filling, bring a cup or so of water to boil in a kettle or small pot. Pour enough boiling water over the dates to fully submerge them, and let soak until soft, about 10 minutes. Drain the water, then add the dates to a food processor or blender. Add the melted butter, brown sugar, and cinnamon, then process until smooth. You may need to scrape down the sides once or twice. Set aside until ready to use, or, if made the night before, refrigerate.
  5. The day of: Generously flour a work surface and scrape the still-cold dough onto it. (No need to let the refrigerated dough come to room temperature. It will warm during the second rise, and I find that a cold dough is much easier to roll and work with.) Roll the dough out to a large rectangle, about 10”x13” or thereabouts, and about 1/4" in thickness. Spread the date mixture across the dough, leaving a 1/2" border around the edges. Gently but tightly roll the rectangle into a log. Rolling the rectangle width-wise will give you larger cinnamon rolls with more swirls; length-wise, smaller. Either way, pinch the seam shut and place the log seam-side down.
  6. Using unflavored dental floss or a serrated knife, gently slice the log into about 8 to 10 rolls, a little more than an inch in width. If using a knife, cut by gently moving the knife back and forth in a sawing motion to avoid pressing down on the dough -- that should help it keep its shape. It’s important to use a serrated knife rather than a smooth-edged one.
  7. Place the rolls, cut-side down, into a 9-inch pie plate or cast-iron skillet, or an 8x8-inch square baking dish. Leave some space for them to expand; if you run out of room, bake the extras in individual ramekins or free-form on a baking sheet. Cover loosely with plastic wrap or a damp towel and let rise for about 45 minutes to an hour, or until rolls are almost doubled again. (If you like, you can do an overnight rise in the refrigerator at this point as well, or even freeze the rolls, well-wrapped. Either way, just bring the rolls to room temperature before baking. See Notes below for a Christmas schedule!)
  8. About 30 minutes before you’re ready to bake, preheat the oven to 350 F. When the rolls are nearly doubled, brush them with the remaining egg white, if you like, then bake about 18-22 minutes, or until rolls are just barely golden in spots -- this will ensure that they’re still nice and soft in the center. If using a cast-iron pan, you may want to take them out a minute or two earlier, since the pan retains heat so well and will continue to cook the rolls for a bit afterwards.
  9. While the rolls cool, make the frosting. Using an electric mixer or plenty of arm strength, beat the butter and cream cheese together until smooth. Add the confectioners’ sugar in batches, beating vigorously after each addition until smooth. Finally, add the vanilla and the maple syrup and beat again to incorporate. If you want more of a glaze than a frosting, add the milk, a tablespoon at a time, until it reaches your desired consistency. I added about 2 tablespoons. Spread over the rolls while still slightly warm to let the frosting melt into the crags, and enjoy immediately.

Notes

For a traditional cinnamon filling, use 4 tbsp (1/4 cup, 2 oz or 1/2 stick) softened butter, 1/2 cup packed brown sugar, and 1 tbsp cinnamon. Spread the butter over the dough, then sprinkle the brown sugar and the cinnamon evenly over top.

If your milk is having trouble foaming and your yeast is fresh, it might be because the milk needs scalding first. Heat the milk until it just bubbles at the edges but does not boil, then cool until just warm to the touch. Add the yeast and see if it foams this time, then proceed as normal.

For Christmas: If you'd like to bake these first thing in the morning on Christmas Day, here's what I'd do!

10 AM, Christmas Eve: Make the dough on Christmas Eve morning around 10 AM. Let rise in the refrigerator for 8-10 hours, or until doubled.

8 PM, Christmas Eve: On Christmas Eve ... eve, make the filling, roll out the cold dough, shape, cut, and place into the baking pan or skillet. Let rise in the refrigerator again, covered well, this time overnight.

Christmas Day: On Christmas morning, let the rolls sit at room temperature for about 15-20 minutes while the oven preheats, then bake as directed, make the frosting while they bake, and enjoy warm, with a side of presents. 🙂

http://tworedbowls.com/2015/12/02/sticky-date-cinnamon-rolls/

45 comments

  1. says:

    December 2, 2015 at 6:44 am

    There is nothing like the aroma of yeast rolls in the oven. Oh my! What a welcome to whomever enters the house. I love baking but I haven’t tried making rolls with dates — cookies , yes but not rolls. Time for a change. Your photos are beautiful.

    • tworedbowls says:

      December 4, 2015 at 10:44 am

      I’m just the opposite of you and have never tried making cookies with dates! We should trade 🙂 Thank you so much for your kind words, Marisa!

  2. ksenchan says:

    December 2, 2015 at 6:48 am

    I have NEVER thought of putting dates in cinnamon rolls, and now that you’ve done it, I can’t help but wonder how that wasn’t an obvious pairing! It’s clearly a match made in dessert heaven.

    Also, your Thanksgiving sounds like a dream. I love when I get to just do nothing with my family, except enjoy their (oft annoying) company.

    • tworedbowls says:

      December 4, 2015 at 10:48 am

      My feelings exactly!! All the things that used to annoy me are just more and more endearing these days. If I could I’d go back and tell my bratty younger self to just chill and enjoy it! Hope you had a wonderful Thanksgiving too :):) and thank you for such kind words!!

  3. Erica says:

    December 2, 2015 at 8:33 am

    My dad would go crazy for these, I might just surprise the family with a pan this winter! Maybe two pans, I probably would eat one all by myself heh. Lazy family holidays are totally the best, I’m glad you had a happy Thanksgiving lady!!

  4. says:

    December 2, 2015 at 8:53 am

    THESE SOUND AND LOOK INSANE. Your way of describing food = perfection. I’m loving your obsession with dates–I’m thinking it’s gonna help me finally get through the container of dates that has been languishing in my fridge! So much love for these gorgeous rolls ❤️❤️❤️

  5. says:

    December 2, 2015 at 9:00 am

    These are stunning! Glad you got some downtime on thanksgiving. I love dates too. I formerly thought they were purely the stuff of grandmas, but now I put them in salads, I sweeten almond milk with them, etc. What you did here is amazing. These rolls look perfect. So rich! I want to reach in and grab one!

  6. says:

    December 2, 2015 at 9:04 am

    So I’m not sure I’ve ever been more excited for a post to hit the blogosphere in my whole life. I share your opinion (formed at the ripe old age of 10 myself) that a cinnamon roll should be gooey and soft on the inside, almost as if it were underbaked. And the inclusion of dates? And cream cheese frosting? Yep, that’s bringing it to a whole new level of perfection.

    PS: “And you cannot be gloomy when you have cinnamon rolls. That’s just science.” Hahaha YES. It is science and I believe that if we search long enough we can find some data to support this hypothesis. 😉 😉

  7. says:

    December 2, 2015 at 9:41 am

    omgosh, your thanksgiving sounds so incredibly perfect (and btw, i was totally waving from across the border in NC!). sticky, gooey DATE bunzzz sound so perfect for this time of year, but especially on this gloomy day. can’t get over those perfect swirls, girl 😉 happy holiday season to you! xo

  8. says:

    December 2, 2015 at 9:59 am

    I think you and Michael would be BFFs since all he ever wants to eat are cinnamon rolls and now the dates in here, I think he’s going to be in heaven! Glad you guys had a lovely Thanksgiving 🙂

  9. says:

    December 2, 2015 at 12:09 pm

    Cinnamon rolls are totally the best thing ever AND are perfect for Christmas baking. You definitely took the traditional recipe up a notch with this date version. Your love of dates makes me so happy!!! Keep it up friend!

  10. says:

    December 2, 2015 at 12:17 pm

    ohhh, these cinnamon rolls look so fluffy and delicious. I love your description of them and the peaceful baking, it makes me feel so happy and warm inside. So glad you had a great Thanksgiving, and happy rest of the holidays Cynthia!

  11. claire says:

    December 2, 2015 at 12:25 pm

    I’m fully behind this filling. The best kind of Sticky. 💛.
    Lovely to see a few gram weights creeping in too. I can only back their increasing inclusion. Thanks for listening to my prior pleading of their case. It makes it so much more likely I’ll actually try these recipes out for myself.
    #scalesforlife

  12. says:

    December 2, 2015 at 1:44 pm

    These cinnamon rolls look wonderful! I am always reluctant to make them because of all the sugary filling you have to put in them. I love this idea of putting in dates instead! Makes me feeling LOADS better about making them! And my tummy will be very happy too 🙂

  13. says:

    December 3, 2015 at 2:40 am

    This is genius, Cynthia! I mean, cinnamon rolls are usually a heart attack but suddenly I feel…safer..?? that it contains dates, full of nutrients! (for the most part) 😉 You make them look so gorgeous that they deserve a display in a hipster LA cafe or something.

  14. says:

    December 3, 2015 at 6:57 am

    I just love this, Cynthia! Cinnamon buns have been a long christmas tradition in our house, growing up my mom would spend the weekends before the 25th making big batches of cinnamon buns, the house would smell like heaven. But then she would freeze them or give them away and we would have to wait until Christmas morning to eat ours. After having moved out I keep the tradition alive, and still only make them over the holidays, much to my husband’s dismay! Anyways, just to say that I get your love of buns! And that date filling is just perfect. I had to laugh at the cinnabon comment – that smell was too much. Hoping your holidays continue just as they started – not very exciting but so totally awesome! x

  15. says:

    December 3, 2015 at 10:04 am

    Best best best filling in the world, Miss!!! So glad to hear your Thanksgiving was boringgg. That is ny favourite way to celebrate holidays- just do family things and eat all the food. No need for fireworks of drama (though families have that too and I say to hell with it).
    You did right by these cinnamon rolls. I’ve been dreaming of cinnamon rolls with a dried figgy component because I love fig seeds so this is oerfect inspiration for it. Great photos too!! Thank you for the recipe!

  16. says:

    December 4, 2015 at 9:09 am

    In. love. with. these. Your writing, these photos, makes me want to get in the kitchen to bake these up right now! Cannot wait to try the sticky date filling!

  17. Helen says:

    December 4, 2015 at 2:40 pm

    Hi Cynthia! I would love to give these as gifts, but am worried they might not stay fresh for very long. How long do they stay soft and edible, in your experience?

    • tworedbowls says:

      December 6, 2015 at 4:01 pm

      Hi Helen! Oh my gosh, a friend who gave me a cinnamon roll as a gift would be my favorite person, what a great idea!!! But yes, the timing might be tricky — I do think these are best the day of. Still, they will keep their soft texture for a day or two, especially if you can store the rolls unfrosted and tightly sealed at room temperature, and if you microwave them for a few seconds before eating. (If frosted, they’ll likely need the fridge because of the cream cheese.) Maybe you could package the roll tightly wrapped and the frosting separately, and include instructions to warm the roll first before adding the frosting? I hope that helps and hope you like them if you try them!!

    • tworedbowls says:

      December 6, 2015 at 4:02 pm

      Oh my gosh, my fingers are crossed that you enjoyed them!!!! Thank you so much for trying the recipe and stopping by!

  18. says:

    December 8, 2015 at 1:17 pm

    Hai! I made these for breakfast because it’s not like I have to pack my bags for a long ass trip or anything (I also painted the ceiling so my priorities have been off for a while now.) You are right about every single aspect of them. They are like little pillows I love them!!! I needed a little winter coziness before my tropical Christmas so this + Christmas lights on one window were pure joy.

    • tworedbowls says:

      December 8, 2015 at 1:59 pm

      EDLYN!! You just made my day! Ahhhhh I’m so happy you made and liked them, THANK YOU so much. I would totally procrastinate packing for cinnamon rolls, too. And yay for our tropical Christmases! I hope you’re headed somewhere wonderful and that you have the most relaxing, joyous holiday. 😀

    • tworedbowls says:

      December 8, 2015 at 2:00 pm

      Ooh and PS — did you try the figgy filling?! That was so genius, I’ve been dreaming about a figgy remake ever since you mentioned that!

  19. says:

    December 9, 2015 at 1:41 pm

    It sounds like you had the perfect kind of relaxing Thanksgiving weekend, and these rolls are GORGEOUS. We always have cinnamon rolls on Christmas morning at my house, but from a can … hehe. Yours would make a lovely substitute!!

  20. Wendy says:

    December 12, 2015 at 8:20 pm

    Thank you for this wonderful recipe inspiration. I gave these a test run today (in advance of the holidays), and they were amazing. Your instructions were especially helpful. Since I like cardamom with dates, I substituted 1 tsp ground cardamom for the cinnamon. I didn’t think they needed a bit of frosting–they were that good!

    • tworedbowls says:

      February 17, 2017 at 10:11 am

      I’m incredibly late, but wanted to thank you for this wonderful comment — I’m absolutely thrilled you liked the rolls (and love the cardamom substitute, what a great idea.) Thank you so much, Wendy!

    • Mark says:

      July 21, 2016 at 12:45 pm

      I’ll second the call for savoury crunch – I sprinkled a light dusting of cinnamon and a handful of pumpkin seeds (I have a nut allergy) on top, and it was really super!

  21. Mark says:

    July 21, 2016 at 12:43 pm

    Thanks so much for this recipe – I’ve made it three times in the last two weeks!

    I’m a big fan of whole grain flours but my wife is sensitive to (whole) wheat so I replaced half the all-purpose flour with a heaping cup of whole spelt flour (150-170g) and that has worked really well. I have used conventional whole spelt and sprouted whole spelt and both turn out great! I also use kefir in place of buttermilk.

    One thing I found is that the recipe turns out better with the first ferment in the fridge for 12-24 hours. I tried doing the first ferment at room temp and the second ferment in the fridge, the first time I made these, and they didn’t rise as much. Maybe my first ferment was too long? Anyway, super recipe!

    • tworedbowls says:

      February 17, 2017 at 10:10 am

      A very, very (very) belated thank you for this, Mark! I’m really so thrilled you liked the rolls, and especially love that you used spelt flour — so good to know. Also good to know that it’s best to have the first rise in the fridge. Thank you so much again!

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