5 Ways to Deepen Your Relationships This Season

5 Ways to Deepen Your Relationships This Season

deepen your relationships

A deep connection starts with interest, open-mindedness, and paying attention…

April Mae Monterrosa

Not all relationships are created equal.

Even our most important relationships can vary widely:

Some naturally deepen over time. Others may require some more proactive nudges to help them along.

Today, we’re continuing our series on relationships during the holidays with a look at some simple ways to deepen your relationships with the people in your life.

Read on for 5 tips to help you deepen your relationships this holiday season (and beyond!):

1. Reflect on your current relationships.

Before you take any steps to deepen your relationships, it’s important to reflect honestly on how things are going right now.


Think about the relationships in your life. Which ones stand out as the strongest? What do you appreciate most about these relationships? Which relationships would you like to take steps to deepen? Why?

2. Take 1 new step.

Deepening your relationships doesn’t have to be an elaborate process. In fact, major change can occur through a series of small steps taken over time.


  • Reach out: The next time someone in your life crosses your mind, take a moment to reach out via text or phone call to let them know. 
  • Get curious: Go beyond the usual small talk to learn more about your friends and family. If they share a detail about their week (e.g., a movie they’ve seen), ask some follow-up questions about it to better understand how it resonated with them.  

3. Plan ahead.

Life is busy. It’s both a fact… and an all-too-convenient excuse to avoid the healthy work of maintaining relationships. By being proactive about planning time to connect with the people in your life, you’ll convey your care for them. (And you’ll have a much better shot at actually spending time with them!)


Pull out your calendar and scan through the next year. Fill in any birthdays and other important dates for the people in your life. Schedule standing plans (e.g., monthly lunch date) as far in advance as you can. Keep your calendar updated with new items that come up (e.g., a friend’s scheduled procedure) to help you remember to reach out and check in when the time comes.

4. Lean into the challenges.

It’s easy enough to connect over life’s highlights: the celebrations, the good news. It can be harder to connect over the frustrations and hurts we experience… and yet this is an important part of deepening your relationships.


Model the kind of sharing you want in your relationships by taking a risk and sharing something you’re struggling with right now. Then express gratitude for their taking the time to listen.

5. Change up your habits.

It’s a simple fact of life: We tend to fall into patterns that are easy and familiar to us. And while this isn’t necessarily a bad thing, falling into routine ways of relating to the people in our lives can prevent our relationships from deepening over time. So, the next time you’re tempted to default to the usual choices for your next gathering, challenge yourself to think outside the happy-hour box and come up with a new way to spend your time together.


Plan an interactive activity for your next get-together. An outdoor adventure, a game night, an escape room– anything to get you and your friends/family working together and/or enjoying each other’s company in new ways!  

Enjoy this post? You might also like:

How to Practice Gratitude When You’re Not Feeling Particularly Grateful
Self-Compassion: 4 Ways to Start Practicing It Today
Your Emotional Wellness: 50+ Ways to Support It

Ready to learn more skills to help you deepen your relationships?