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Overcoming Loneliness and the Single Holiday Blues


Kait and JJ Tomlin

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Kait and JJ tackle a sensitive topic today. They’re talking about loneliness and the holiday blues as we enter the holiday season. 


Hey podcast fam!! Surprise!!!!!! We’re back with a new little mini season already! We’re talking about all things being SINGLE DURING THE HOLIDAYS. Talk about the struggle being REAL. We’ve all been here. Today, we’re specifically talking about loneliness during the holidays and the holiday blues. 


Why does this happen? Why do we experience loneliness and the holiday blues as singles? Often, the holidays are known as “cuffing season.” Really, this just means the cold autumn and winter months being seen as a period when it is especially desirable to enter into a romantic relationship. While you may LOVE (us too) holiday RomComs, if you’re single it can be a reminder of what you DON’T have. 

The holidays are often a time of EXPECTANCY. Obviously, biblically it’s a time of expectancy because we’re waiting to celebrate the birth of Jesus Christ. But, there’s often expectancy in our personal lives when it comes to dating, love and romance, our families and what we wish was the relationship with our families, or sometimes friends. 

What is loneliness?

Loneliness is probably the first thing that surfaces in cuffing season. BTW cuffing season, according to urban dictionary, it’s cold and lonely so people are desperate to get cuffed (literally handcuffed to one another) for a relationship. So the origin of cuffing season is LONELINESS. 

The reality is that if you are single, you will experience times of loneliness. There will be times where you feel isolated from others in some area of your life. There’s this underlying feeling of being UNINVITED, excluded, like you’re late to the party, maybe you’re unwanted, forgotten, left behind, unworthy, or simply not understood. However, there IS a difference between LONELINESS and BEING ALONE. Often, being lonely has nothing to do with being PHYSICALLY absent, but has everything to do with FEELING disconnected, like you have a lack of connection with people, or feeling misunderstood or rejected. In many ways, loneliness is an assumed rejection. Maybe you feel rejected by family, by friends, by romantic interest, by God, or even yourself. 

You MIGHT be alone and be lonely. But, more often you can feel very lonely and still have people around you, still going to holiday parties, still have plans for Christmas and Thanksgiving, AND still feel lonely. 

Holidays for a lot of people, if you’re not really connected with your family, if your family isn’t a family that deeply enjoys each other, fulfills each other and satisfies that relational need between one another, holidays can actually be incredibly LONELY and sometimes BORING in that sense. Boredom can reveal loneliness. There are TONS of situations where people can feel lonely. 

Sidenote: We actually have a GREAT masterclass we taught on loneliness over a year ago, in our old program, The Singles Academy, that is available in Patreon now (tier 3). It was our first one and it’s a really POWERFUL masterclass and was many people’s favorite one we did. Just go to 

6 Different Kinds of Loneliness

This is from Elisa Morgan, we think this is really interesting because there’s not just ONE kind of loneliness. We often use it as a blanket term, however there are many kinds and it’s super clarifying. 

Emotional loneliness - ”No one knows or understands my feelings, nor wants to hear them.”

Relational loneliness- ”No one knows the real me and accepts me.”

Missional loneliness- “My life has no meaning, I do not have a clear purpose.”

Spiritual loneliness- “I am cut off from God, I cannot hear HIM, see Him, feel HIM” or “I feel like He has forgotten about me.” 

Physical loneliness- “I have no one to share the load or these life experiences with.” 

Situational loneliness- “I am being excluded or left out of events or situations… the pandemic. “

It’s important to know which one of these types of loneliness you’re feeling in this season. Which one comes up for you the most in this season? If you can identify the type you’re feeling it’s easier to remedy it and fix it. 

Single Holiday Blues

There’s holiday blues in general, if maybe you’ve lost a loved one. There’s the absence of you used to have this experience and now you don’t. Then there’s the single holiday blues because you’re single and maybe you’ve never had it, but you’ve always seen it. The holidays are SO romanticized. We want to clarify though, when we say holiday blues it doesn’t necessarily mean depression, though it CAN lead to depression. The term holiday blues really comes from having high expectations and having a large amount of loneliness, and maybe a lot of compounded stress, which can lead to feeling down. Sometimes this can be temporary, but they can be serious if they last for more than two weeks, sometimes that can lead to seasonal depression and/or anxiety. There are a LOT of stressors in this season. Pressures to attend or host parties, buy gifts, and spend time with family can be stressful. The one thing all these stressors have in common is that it’s expectations from OTHER PEOPLE. None of them have to do with YOU, and none of them have to do with GOD. If you’re a slave to other people’s opinions and expectations of you, the holidays are the WORST. 

There was a study done by the National Alliance on Mental Illness (NAMI). They found that… 

  • 66% have experienced loneliness. 
  • 55% found themselves remembering happier times in the past contrasting those happier times with the present. 
  • 50% were unable to be with loved ones. 
  • 24% of people who already have a mental health condition find the holidays make it a LOT WORSE for them. 

How to Combat and Grow Through Loneliness and the Holiday Blues

First, disappointment is rooted in failed expectations. This isn’t to say you can’t have expectations. We also don’t think this means that you swing the pendulum the other way and have ZERO expectations, that’s a little cynical. Keep expectations low, reasonable, and clear with your boundaries. 

Second, setting boundaries. Know what your emotional and physical boundaries are in this season. Maybe it’s boundaries in the type of conversations you’re going to engage with, the kind of food you’re going to eat because that affects your mental health, how much sleep you’re getting, how much you’re drinking. The holidays can be way more enjoyable when you set boundaries. Remember, if you set the boundary, you are the keeper of the boundary. You can’t expect that other people are going to completely adhere to your boundaries. Set them and make them clear, then you need to adhere to them. Meaning, if someone is trying to go against your boundary, you have to stick up for yourself. You’re not the victim to someone crossing your boundaries. Be very compassionate with yourself. It’s totally okay if you’re having a lot of feelings, if you need to reset and recalibrate your boundaries, it’s okay to say no to things. 

Third, live in reality and create new memories. Instead of daydreaming, fantasizing, living in the past, go make new memories! When we fantasize it makes us LESS grateful for the reality in front of us. Take it upon yourself to make the plans and invite people in. Never be the excuse for why something isn’t happening. 

What if your loneliness was a gift that urged you into a situation where God was your only enjoyment and satisfaction in front of you? Wouldn’t that be worth it? 

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Kait Tomlin

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Kait Tomlin is a best-selling author, speaker, popular relationship coach, and the founder of Heart of Dating. She helps thousands of men and women on their journeys through the conversations on the Heart of Dating Podcast, which launched in 2018.

Through her ministry, Kait’s mission is to empower both men and women to have the courage to own their story, walk in victory, thrive with purpose, and discover clarity and vision in their life and relationships. In her new book, Thank You for Rejecting Me: Transform Pain into Purpose and Learn to Fight for Yourself, Kait vulnerably shares how she grew through her deepest, darkest rejections and offers readers the tools to heal from the past, take back their power, and walk in strength, victory, and love into their future. Kait currently lives in the Los Angeles area with her husband JJ and their pups Lovey and Teddy. She loves sunshine, walks, Jesus, and lip syncing to Celine Dion.

JJ Tomlin

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JJ Tomlin is a missionary kid born in Belgium, originally from Tennessee, and currently residing in the OC. He currently works in Gaming/E-Commerce, enjoys watching his Tennessee Titans on Sundays with his Goldendoodle Teddy and loves working with Christian men to raise the bar in singleness and dating.

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