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Surviving Single Shaming

with

Courtney Leo

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Today Kait has a conversation with Courtney Leo about single shaming, both the external and internal, that happens during the holidays. 

Introduction

Hiii HOD fam, we’re back after a fun week off for Thanksgiving and we’re coming in HOT with another episode in this mini season on being single during the holidays. Today we have a special guest and member of our community, Courtney Leo! We’re talking all about SINGLE SHAMING. I know, I know, this is a hard hitting one and we’re PUMPED to dive into this conversation today. This is a good one to send to your non-single friends and family so they know how to better support and love their single friends. Let’s get it!!! 

Courtney is hosting a Christmas event for singles on December 4th and 5th. To get tickets go to courtneyleo.com/HOD and use code HODPOD50 at checkout! This is a two-night virtual event and a space for Christian singles to feel seen, heard, and embraced in this holiday season. 

Single Shaming

Where people may unintentionally either ask you things or do things that make it seem like your season of singleness isn’t beautiful or wonderful or full but rather a waiting period to get to that next thing. 

People asking who you are dating at the holidays…

Courtney shares that she feels several things when this question is asked. The first is that it feels like people are looking at her life as a reality show. The other thing that’s more painful for her is family members who she doesn't connect with often, and they’re trying to small talk. The small talk surrounds singleness as if there aren’t other things going on in her life. It feels like an identity badge she’s wearing and being single is how she’s defined by others. It doesn’t hurt because she is single, it hurts because that’s the only thing it seems like they have common ground on, and they don’t have common ground because the family member isn’t single. It seems like a fascination to them. It’s such a vulnerable part of someone’s life, why would I tell someone I only see once a year all about it? We shouldn’t feel pressure to answer all of their questions or tell them the details of our dating life. 

We do think that people mean well, there’s just a lot of lack of empathy. 

So, practically…

First, embrace the sting of it. 

Secondly, remind yourself it’s not someone who is truly doing life with you. They’re trying to genuinely engage with you so they’re grasping at content they can talk about, and trying to let them know they care. 

Family or friends wanting to set you up with random people. The idea that a single person can't just be single. 

It can be an opportunity to lovingly communicate boundaries. Being able to appreciate the intention while also saying no thank you is a powerful tool in these conversations. Underneath that boundary, in the way you’re communicating it, is leading with a generous assumption about them. This also invites us into learning how to respond instead of reacting to someone asking us these questions.

The line “You are SO great, why are you still single?” How did you wrestle with that?

People are trying to come from a place of love when they say this usually. It definitely depends on the situation and the person but, Courtney sometimes defaults to humor. After saying something along the lines of, “I don’t know, ask the guys out there” she’s able to also say, “No, seriously, I really have created a life I love and that I’m really proud of. For me, I want to be with and say yes to someone who enhances that life I have. I don’t want to say yes to somebody just because I want companionship. I want partnership and I’m waiting for partnership.” It really is an opportunity to have a conversation about her being more than her relationship status, and just because she is single does not mean that she’s unhappy. It’s an opportunity to share with someone about the work and the growth you’ve done and if you haven’t then it’s a great mirror exercise to realize how I respond to this, how do I view these questions? If you have a hard time responding to that then it might be good to dive deeper into that with Jesus and coaches and mentors. 

Courtney hears these things pretty often… 

Maybe the reason I’m still single is that I’ve done something wrong. 

The reason I’m still single is because I must have some unconfessed, hidden sin, and once I uncover that, God will give them to me. 

I’m so mad at God, I know He’s a good God who gives good gifts, so if I’m not receiving the gift of marriage, then there must be something wrong with me. 

So the opportunity and invitation here is to to unpack…

What do I believe about the character of God? Get in scripture and read about the character of God. How He sees you, how He knows you, and how He loves you. 

A mindset shift. If we’re looking at marriage as a prize, then singleness will always feel like failure. If we look at marriage as an accomplishment, then we’ll always feel like there’s something wrong with us. 

What would it look like for us to step into trusting the Lord with this season we’re in? 

Looking at my life the last year and feeling insecure that once again I am showing up single to Holiday festivities and wondering what I did this past year. How do we combat this?

We acknowledge that feeling with you and hold space for it. Actually letting yourself grieve as a process is huge here. God can handle your feelings and grief. Having grace for yourself and allowing yourself to feel those emotions is kindness to yourself. It’s really hard to self criticize when you’re operating in so much self love for yourself. 

Jesus sees you, and understands you. The actual reason for this season is Jesus’ birth not the rom coms and cuffing season. 

Remember to grab your tickets for ‘Tis the Single Season at courtneyleo.com/HOD and use code HODPOD50 for 50% off! 

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Courtney Leo

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Courtney is an authenticity coach, podcaster, speaker, and champion of growth. As a Christian single navigating her 30s, Courtney's life mission is to empower others to live life authentically through exploring their unique design, practicing self love, walking in confidence, and resetting mindsets. After walking through her own journey of toxic jobs, churches and relationships, Courtney authentically shares her journey of finding her voice, setting boundaries, moving past people pleasing and finding true freedom…unmuted and unfiltered. She is a cheerleader for singles to live full and free single lives by discovering who they are, finding alignment with God’s design and stepping into full abundance.


Courtney encourages her community to embrace every part of their stories, welcome the messy, sit in the unknown and normalize imperfection. You can find her hanging out with her dogs, Cooper and Shadow, while sipping an iced coffee and planning her next solo date or wild video for social media.

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