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27 Month Milestones: Asking Why & Playing Pretend

  • Kaylie Estrada
  • Nov 12
  • 4 min read

Discover the 7 new skills your toddler will be practicing this month!

Toddler kicking a ball.
At this age, your toddler will be able to kick a ball with more accuracy!

At 27 months old, your toddler might surprise you with just how busy and curious they are at this stage. They’re full of energy, eager to move around, and starting to ask questions about anything and everything they see. You’ll notice stronger coordination and focus as they experiment with new ways to move, play, and communicate. Whether they’re jumping with both feet or asking “why?” for the first time, they'll make sure to show you just how much they are learning.


The 27 month milestones are divided into five main areas: Gross Motor, Fine Motor, Cognitive Development, Social-Emotional Growth, and Communication. Each area brings its own kind of progress ranging from physical control to emotional understanding and early language expression.


Is your baby up to the challenge?


At this age, your child is busy connecting thoughts, actions, and feelings in new ways. They’re testing limits, practicing independence, and often looking to you for reassurance when things don’t go as planned. This balance of confidence and comfort is an important part of learning and integrating new skills. Each new experience, whether successful or not, helps them to better understand their surroundings.


Toddler feeding a doll.
Toddlers this age will love to play pretend.

Why this month matters


During this time, your little one is learning how to balance their abundance of energy with early self control. They’re asking more questions, showing signs of empathy, and beginning to express their preferences to you with words instead of gestures. Their growing vocabulary helps them to communicate their ideas and describe the world around them, and their new motor skills give them a little more freedom to explore it. Each new milestone this month adds another layer of independence and confidence.


What are the 27-month milestones?


Your toddler’s Gross Motor Development this month is all about movement and balance. You might see them confidently kick a ball over to you or jump with both feet off the ground for the first time! These playful actions show growing strength in their legs and better coordination overall. With every hop and kick, they’re building the control needed for more complex movements in the months ahead.


In Fine Motor Skills, everyday routines become opportunities to practice independence. This month, they may be able to turn the faucet to wash their hands; with a boost up to the sink of course. This is a big step that requires both strength and focus. It’s a small action that shows how capable they can be when given the chance to try out small skills on their own.


Their Cognitive Development is blooming as they begin to explore the word “why”; asking about anything they might be curious about. You might notice them asking more questions about the world around them, such as where things come from, how they work, or why something happens. During this time, they are also showing more early problem-solving skills by being able to stack toy rings from largest to smallest. This skill is impressive because it requires planning, focus, and observation.


In the area of Social-Emotional Growth, imagination takes over. Your toddler may begin caring for their favorite stuffed animal or doll as if it were alive, feeding it, hugging it, or even tucking it into bed. This behavior reveals empathy and a growing awareness of relationships, which helps them understand emotions in both themselves and others.


Their Communication Skills are continuing to grow quickly. You’ll most likely hear them use some simple adjectives like “big,” “small,” or “red” to describe objects, and pronouns like “me” and “mine”. These words give them new ways to share their thoughts, claim their belongings, and express themselves to you or those around them.


The 27 month stage is full of fun surprises. Your toddler’s curiosity, imagination, and determination will be sure to keep you on your toes, but they’ll also fill your days with laughter, discovery, and fun. Take time to enjoy their small achievements because each one is a step toward even bigger milestones on the way.


Fledglings Flight app and subscription box.

How many of this month's milestones has your baby mastered?


Toddlers grow on their own timelines, and being aware of the 27-month milestones helps you celebrate progress as it happens. From jumping with both feet to naming colors or washing hands, each new skill brings a little more confidence and personality. With a Basic Membership for just $2 per month, you can track all 812 milestones your child is expected to reach by age 4. Stay on top of your baby’s progress and celebrate every exciting new skill along the way!


Create a free account with Fledglings' Flight and get access to 4820 screen-free, play-based exercises. That is 100-200 exercises each month that you can start doing with your baby from the day that they are born to help them develop into the best version of themselves. In addition, your free account gives you access to 1200+ articles on child development to keep you informed while you help to navigate your child's developmental journey.



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