Good Eats and Sweet Treats from My Small Boston Kitchen

Soft and Chewy Chocolate Chip Pudding Cookies

I remember back to a day not long ago, when I was lamenting the fact that this winter had brought us no snow. Little did I know what sort of wrath Mother Nature had in store for us! Last week, the Blizzard of 2015/Snowmageddon/Snowpocalyspe arrived here in New England, and it dumped over 2 feet of snow across the area. If anyone was feeling the snow shortage before, they certainly weren’t after that. I had two snow days in a row working from home, which were largely filled up with shifts of shoveling and blanket cuddling.

That being said, working from home provided a fantastic opportunity for me to finally get my home office sorted out! My home office had become pretty neglected over the years. My desk was covered in loose papers, and most of my other furniture in there was broken. However, after sorting through all of my old things and storing all my files and paperwork into these really useful boxes 35l it started to look a bit more like it used to again. I just need to invest in some new office furniture now and then my workspace should be back to normal!

Okay to be fair, apart from sorting out my office there was far more blanket cuddling than work completed, but STILL! My body felt the after-affects of those hours of shoveling for daysssss. My roommate and I are fortunate enough to have a driveway, so we were safe from the plows and parking hysteria on the streets, but it also meant that we had to shovel out an entire driveway, instead of just one car on the side of the street. We tag-teamed those 2+ feet of snow and powered through, but by the time I had moved all the way to the end of the driveway where the plow slush lives, I had no energy left. Even worse, the stuff at the end is far and away the heaviest!

Chocolate Chip Vanilla Pudding Cookies - Sweetly Serendipity

I saw our neighbor out with his snow blower, and when he finished his property he came over and helped me with the end of our driveway. He and his wife have been the best neighbors from day one, when his wife came over and introduced herself, and told me she’d have my back as long as I lived in our house. They’re colorful, friendly people, and have an … enthusiastic design sense for EVERY HOLIDAY EVER CREATED, to go along with their charming old ‘Medfuhd’ mentalities. Needless to say I really adore them, so as soon as I saw him approach with that snow blower last week, I thought I’m gonna make that man some cookies.

Chocolate Chip Vanilla Pudding Cookies - Sweetly Serendipity

So after I’d sufficiently thawed under a mountain of blankets, I found this recipe and headed for the kitchen. A couple months back I made chocolate pudding cookies and loved them, so I figured the vanilla variety would be a no-brainer. Turns out I was right — so right that these cookies unfortunately never made it to the man across the street. Yours truly has slowly been devouring them instead. I guess what he doesn’t know can’t hurt him, so he can’t really he disappointed that he didn’t get any cookies, but I do feel a little bit guilty every time I go to grab one. Just a little bit… 🙂

Chocolate Chip Vanilla Pudding Cookies - Sweetly Serendipity

So I’m telling you here – next batch goes to the man across the street! If we keep getting more gosh darn snow (which we’re supposed to, says the weatherman…), I should have ample opportunities for repayment. That is, if I can get out the front door. At the time of publishing this post, we’re up to 4 feet of snow in 10 days, with an estimated 2 additional feet coming in the next 10.

So, who wants to move to Mexico?!

Chocolate Chip Vanilla Pudding Cookies - Sweetly Serendipity

Oh, and about the cookies… they’re amazing. Especially if you just barely cook them, so they’re like chocolate chip cookie fudge amazingness. For real — that’s definitely a thing. These cookies are wildly delicious straight outta the oven, but equally amazing after sitting on the counter for a few days, or fresh from the freezer. Any way, all ways, they are incredible. Chalk it up to the pudding mix, and perhaps an extra dose of love in this batch. I promise you they’ll fight even the harshest winter blues.

Chewy Chocolate Chip Vanilla Pudding Cookies


  • 3/4 cup (1 1/2 sticks, 12 tablespoons) unsalted butter, softened
  • 3/4 cup light brown sugar, packed
  • 1/4 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1 cup all-purpose flour
  • 1 cup white whole wheat flour
  • One 3.5-ounce packet instant vanilla pudding mix (not sugar-free and not 'cook & serve')
  • 1 teaspoon baking soda
  • 1/4 teaspoon salt
  • 2 cups semi-sweet chocolate chips (I used 1 bag of Trader Joes chunks)


  1. In a large bowl, or the bowl of a stand mixer fitted with the paddle attachment, combine the butter, both sugars and beat on medium-high speed until light and fluffy, 1-2 minutes. Add the eggs one at a time, beating well after each addition. Add the vanilla, and continuing beating until the mixture is creamed and well combined, another minute or so.
  2. In a separate medium bowl, mix both flours, pudding mix, baking soda, and salt just to combine. Ass dry ingredients to the wet ingredients, and beat on low speed until just combined. Scrape down the sides of the bowl, add the chocolate chips, and beat on low speed until the chips are just incorporated.
  3. Using a large cookie scoop or your hand, form about 14 equal-sized mounds of dough, roll into balls, and place on a large plate or tray. Cover with plastic wrap, and refrigerate for at least 2 hours, or up to 5 days. Unchilled dough will bake up thin and flat, so don't do it!
  4. When ready to bake, preheat your oven to 350 degrees F. Line a baking sheet with a silicone baking mat or parchment paper, and place dough mounts on your baking sheet spaced about 2 inches apart. Bake for about 11-12 minutes, until the edges of the cookies are set and the tops are just set. Be careful not to overbake! The almost-undercooked texture of these cookies is what makes them so magical.
  5. Let cookies cool on baking sheets for at least 10 minutes before devouring them. If not eating right away, you can let the cookies cool completely on the baking sheets. They will firm up as they cool.
  6. Cookie keep in an airtight container at room temperature for up to a week, but freeze well for much longer.

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