If the holidays bring up nerves about being single — the questions, the pressure, the comparisons — this episode is your Holiday Dating Survival Guide. It’s a warm, grounding replay packed with self-compassion, boundaries that protect your peace, and real scripts for handling conversations about your dating life.

Inside, Lily shares:

• how to release the self-judgment we’ve all internalized from patriarchal socialization (that says that coupled women are “ahead” of single women)
• why self-compassion is the antidote to self-judgment (and how to practice it daily)
• three phrases from Dr. Kristin Neff’s work to use when you’re feeling nervous, jealous, conflicted, or despairing
• how to identify the desire underneath your fear so you can move forward from a grounded place
• what to actually say when someone asks, “So… how’s your dating life going?”
• how to use boundaries, a self-care plan, and a joy-building plan to support yourself this season
• why you don’t owe anyone your story — and how to practice unbothered energy
• how to feel less alone, even if you are the only single person in the room

This episode is a reminder that no matter what happened in your love life this year, you are worthy of celebration. You get to take up space. You get to be proud of yourself. You get to feel belonging.

✨ This is the final episode of 2025. The podcast returns in January 2026.

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Show transcript:

Lily @ Date Brazen (00:00)
Hey, gorgeous friend. I am so glad that you’re here. Happy holidays. Happy December. I am recording this in December 2025. It is about to be 2026, which I cannot believe. It has been such a wild, wild year. And I’m so grateful that you listened along this year to the podcast, that you were in this community. You were.

Support means the world you listening and subscribing means the world you leaving reviews leave means the world to me I’m just so grateful for you I get to show up and do this job every single day because you’re here and so I just wanted to express my gratitude and say thank you And I also wanted to remind you that no matter what happened this year whether you made progress in your love life Or you don’t feel like you did or you met somebody amazing or you didn’t I just want to let you know that no matter what, you are worthy of celebration.

You are worthy of celebrating yourself. And I hope that you take inventory of your wins from this year, the things that you’re proud of this year, maybe a boundary that you set or an ask that you made or ⁓ something, an opportunity that you went after or attracted. I really want you to ground in self-celebration and ⁓ in doing so, build some pride in yourself.

Know the holidays can be a stressful time to be single, especially if you’re surrounded by coupled people, and especially if your needs feel sidelined. And so I really want you to take this opportunity to take a deep breath into the fact that you get to be proud of yourself and you get to take up space.

And maybe if you have a friend who you can send this episode to, you can text each other your wins, what you’re proud of from this year to create some community and belonging. You are worthy of self celebration right now more than ever.

This will be the final episode of the year for the podcast and we will be back in January 2026. And I just wanted to offer this big old hug to you in the podcast.

And today’s episode is a replay from an episode that I did last year on dating during the holidays and navigating potentially complicated or awkward conversations. ⁓ And so I think it’ll really be supportive. And I’m grateful for you. And how many times can I say that? A jillion.

All right, with that, let’s get into the episode.

Lily @ Date Brazen (03:07)
If you are feeling nervous about being single this holiday season, and you’re especially nervous, at the thought of being asked that question, how’s your dating life going? At any holiday table with either a friend who is well-meaning but a little bit nosy and who maybe has been married for a decade and doesn’t remember how hard dating was, or you’re afraid of being asked that question by your nosy aunt who judges you for still being single, okay?

So whatever the question you’re fearing being judged, here’s how to prepare to answer it confidently. Number one, you need to notice where you’re judging yourself.

Now this might sound counterintuitive because I’m talking about other people projecting their BS onto you. First, you need to notice where you’re judging yourself for still being single.

This is deeper than just dating. This is about how patriarchal socialization has impacted how you see yourself in this present moment where you are right now.

Because our world socializes people, especially who are socialized as women, to see themselves as less than if they’re not coupled. I remember this growing up in the deep south.

Single women were not treated as important, quote unquote, as coupled women. And I internalized that at a young age.

And when I was single, I felt behind all the time and I was heaping judgment upon myself, right? Every holiday season, was the another holiday season where I was single, another holiday season where I was being asked questions about my dating life.

I felt like, God, I still don’t have a good answer. And I was heaping judgment upon myself, which only made the situation more stressful.

So it’s a both and of like, their questions might feel really stressful. We’re gonna talk about how to handle those. And your judgment of self might be even more stressful on top of that.

Self-compassion is the antidote for self-judgment. I’m gonna repeat that. Self-compassion is the antidote for self-judgment.

And I know this from personal experience. And you might be listening to me saying like, God, Lily, here you go again about self-compassion or God, Lily, I just started listening to this podcast. What the fuck are you talking about? I just want some dating tips. Give me the good stuff. I’m getting there.

Self-compassion is the road to get there. Okay? So how is it the antidote for judgment? It is reducing cortisol, reducing stress and increasing resilience. And this is from a 2014 study out of Stanford. Now,

Self-compassion is a practice, like any practice, like a practice of going on walks. The more you go on walks, the longer you can walk, like running. The more you go on runs, even if you’re going slowly, the more you can run.

Like a practice of yoga, the more you practice, the more efficient you will be in your practice. The more you will feel the benefits of that practice. Same, same with self-compassion. It is a commitment to yourself.

What kind of commitment is self-compassion to yourself, especially if you’re single at the holidays? It’s a commitment that you’re human, that you’re imperfect, and that’s okay.

That you’re human, you want things, some of them are not here yet, that’s really hard, and that’s okay. That you get to, under all of that, over all of that, you get to have your own back.

That there’s nothing wrong with you for being who you are and where you are right now, and that’s what a self-compassion practice is. It’s radically turning toward yourself like you are worthy of love and support, which you are.

This is your one wild and precious life. And I want you to treat yourself kindly within it because you deserve kindness, because it’ll move you forward faster.

Here are three things that you can say to yourself that are really self compassionate during this holiday season, no matter where you are, especially if you’re judging yourself. Number one, of course I’m feeling nervous, jealous, conflicted.

Despair, whatever you’re feeling. Of course, I’m feeling hard feelings about my love life during this holiday season. Insert context here, because I was socialized to believe that being single was wrong. Sucks, yeah?

So just give yourself, number one, the benefit of your context. Be kind to yourself.

Number two, I’m having a lot of hard thoughts about this. Noticing your thoughts as thoughts and not facts.

The thought, this is another holiday that I’m single and I’m a failure for it, or the thought, Everybody’s judging me because I’m single and I should be judged because something is wrong with me Maybe because I’m single and I’m broken maybe because I’m still single and everybody else is what did they have? What do they do that? I didn’t do what do they have that I didn’t have right all of those thoughts are Just thoughts they are thoughts not facts there are sentences in your brain designed to keep you safe safe from rejection safe from being put out of the cave and dying of exposure that fear is normal.

Those thoughts are human thoughts and they’re not facts. Noticing those thoughts is not facts is a really important practice of mindfulness and self-compassion.

So number one, kindness. Of course I’m feeling this way. Number two, mindfulness. I’m having a lot of hard thoughts. Number three, bring in belonging. I’m not alone. There are so many people that feel this way.

Now, this is so hard if you’re one of the only single people or the only single person in your family or in your friend group. This is a hard one because you might look around and see Lily, no I am, I am really alone.

I’m here to tell you, I coach folks who are single, who are badass, who are amazing, who are bringing so much brilliance to their everyday lives, who also feel difficult around this time. I know and I was there, I remember how difficult it was and how I felt just isolated as fuck.

If I had this skill then of imagining myself in a collective of other people who are right there with me, I think I would have felt better and I think you will too.

Even if you don’t have a buddy right now who is single with you, even if physically you’re the only single person in your vicinity physically, I want you to imagine the amount of people, just listening to this podcast, imagine the amount of amazing, brilliant human beings who are whole right now, creating so much brilliance in their lives who also want a relationship right there with you who are learning how to date with more joy.

I want you to imagine them as all in a room together. There are thousands of people who listen to every episode of this podcast and you are right there alongside with them.

This is adapted from the work of Dr. Kristin Neff, these three pillars of self-compassion, kindness, mindfulness and belonging. Those three things are how you can practice self-compassion, integrate those thoughts into your everyday, say them out loud and often.

To bring in a little more self-compassion when you notice self-judgment, when you notice yourself freaking out. Again, it’s gonna reduce cortisol and increase resilience.

And if you’re tired of me talking about self-compassion on this podcast, buckle up, because we’re not done. We’re not done. I think that this is such an important resource, because it’s not toxic positivity.

It’s not trying to program your brain to have a positive thought right now. It is working with what is right now, which is the only way to actually move forward instead of blaming yourself for having negative thoughts and hard feelings and then saying, I shouldn’t feel that way. I shouldn’t think that way. And then trying to map on a positive thought to it. That’s just toxic positivity.

This is working with what is caring for your nervous system and moving forward. I also love the meditations that are free on Kristin Neff’s website, self-compassion.org.

So first we acknowledge where you might be feeling some self judgment and release that self judgment with self compassion.

Now second, I want you to acknowledge the fear that you have about the holidays and being single, whatever the fear is. And then underneath that fear, there’s probably a desire. And I want you to recognize that desire.

Now here’s what I mean by that. You probably have a desire to feel peace and to not be judged. You probably have a desire for a more self celebratory, joyful, peaceful love life and dating life and life in general.

And if you’re listening to this podcast, you probably have the desire to find and be with the right partner. You probably have a desire to release the negative thoughts about yourself. Like I’m broken or you have a desire. Maybe you would put it as I have a desire to fix the problem, right? I have a desire to fix the dating life, right?

What if desire was to have a dating life that was a reflection of how awesome the rest of your life was. What if the desire was to have a dating life that was boundaried as hell and in which you were confident as hell. All of those desires are wonderful. Welcome them in.

Acknowledge the desire underneath your fear and then write yourself a freaking permission slip to want what you want and to have it. And if that feels a little grandiose, you can write yourself a permission slip to want what you want and to be figuring out how to have it.

And with that permission slip, I want you to renew it daily or weekly this holiday season. What permission do you need to give yourself? What’s the desire underneath the surface?

And for me, when I have a fear, specifically when I’m single, my fear was I’m too much, everybody can smell it on me. I’m single for a reason because I’m too much. I gotta figure this out. Otherwise, everybody’s gonna think that I’m a loser who can’t find a relationship.

All of those fearful thoughts, right? Underneath those fearful thoughts for me, where I wanna feel less alone. I feel like an alien in this situation, in this party. This like, I’m too much, isolation, isolation, isolation. I wanted to feel less alone.

Underneath the fear of I’m broken and I’m never gonna find somebody was, I desire to feel whole right now and I desire to have more hope for what I want in my love life. And on and on, right?

The desires under the surface are totally normal and great and you get to what would you want. And acknowledging what you want underneath the surface of your fear will help you start to figure out how to get what you want instead of everything being clouded by the big fear thoughts. Okay?

Those big fear thoughts are creating a lot of feelings like panic in your body or despair in your body that then create actions like you shut down. Like when somebody asks you about your dating life, you say, I don’t know, it’s fine, it’s fine. And then they only press on more and then you feel shitty for the rest of the day.

Or create actions like trying to get on a dating app and going on all of these dates that you know aren’t right for you. Instead of acting from the fear, acknowledge the fear, care for it with self-compassion and acknowledge the desires underneath.

From those desires, we can do a lot of great powerful work. Instead of operating from a place of panic, what if you integrated the thought or belief, I’m figuring out how to do this. I’m not alone. And then from that place, you could create a little more opening, a little more opportunity.

So for this holiday season, before we get to the tactical boundaries which are coming, how can you experience what you desire to experience? like the desires that you have to feel peaceful, to feel whole, to be on the right path, to finding the right partner.

How can you experience what you want right now before you meet your partner? I am not saying that being single is the same thing as being partnered or that you just need to love yourself more. I’m saying that what you want is more available right now. then you might realize.

And I wanna help you generate the feelings of peace, of self-acceptance, of self-compassion, of hope. And I want you to help create boundaries from that place instead of creating boundaries from the panicked place.

And how do you do this? You do it with three things, boundaries, a self-care plan, and a joy building plan. Boundaries are essentially saying this is okay and this is not okay. Boundaries are centering yourself.

They can be really scary, especially if you were raised or socialized in a space where you were taught that you had to care for everybody else’s feelings in order to survive. Boundaries are a radical act of self-determination, of self-centering.

But even that, like I hear you in the back of my head, I’m like, I hear you saying, but Lily, it’s selfish to set boundaries and it’s selfish to want what I want and it’s selfish to send itself indulgent to center myself. Seriously, so.

This is your one wild and precious life. You could stand to be more selfish, especially in your love life. And by love life, I mean how you’re treating yourself, how you’re going after finding the right partner, how you do relationships on the whole.

How are you treating yourself in your love life? You need to be more selfish and untangling the gnarly things that you were taught about what it means to be selfish that you’ll be alone because you’re selfish or that you’ll, you you won’t find a partner if you’re selfish or nobody’s gonna wanna be around you if you’re selfish.

All of those things are like a gold chain, it’s very fine and delicate, that has been knotted up over years of being taught that in order to be safe, you need to people please, you need to be perfect, and you need to care for everyone around you all the time or else, right? That’s bullshit.

Now I understand that they were safety mechanisms that were keeping you safe and have been keeping you safe. Until then, thank you, safety mechanisms. Thank you for delivering us to this moment, to this podcast, both and it’s time to untangle that shit.

It’s time to start slowly untangling this gold chain and looking at the pieces and being like, okay, this is goes through here. This is an unhurried unfolding of untangling what you were taught about it being bad to center yourself in order to belong. This is untangling work.

You get to want what you want. You get to be selfish. You get to set boundaries. You get to be the priority in your own life.

It doesn’t mean that you’re saying that everybody else’s needs don’t matter. It’s that you’re saying that your needs matter just as much as everyone else’s. In fact, you are the only one who can get your needs met. So they actually matter more, because you’re the one in charge of them.

So boundaries, let’s get into it. Tactically, if you are asked a question like, how’s your dating life going? This is being asked by a person that you’re not in deep trust with. You don’t owe them your story.

Even if you’re a late bloomer, even if you have just gotten a divorce and you told everyone that you were dating three months ago and now you don’t want to talk about it, whatever the case, you don’t owe anyone your story.

And what if you integrated this like self-compassion and you integrated this desire work, you desire to like center yourself and to figure this out and you got to answer from that place of just like unbothered energy of like, it’s going fine, pass the piece.

Unbothered energy is the goal for you just for yourself, right? You don’t have to engage with people, especially people that are not trustworthy to engage with on this topic. Not every friend is the right friend to talk about your dating life with. Not every family member is the right person to talk about your dating life with.

And the problem that I got into when I was single and I felt such… deep feelings of despair in my dating life for feeling like a late bloomer is that I would look for external validation all the time about my dating life.

I would say something like, it’s not going well. Like, haha, will you look at my dating profile? Like, I think it’s good. Right? Outsourcing my agency. I was trying to get validation because I felt so like, like something was wrong with me.

And I’m here to tell you that we’re figuring this out together. You get to talk to people and invite people into your story who you trust. and it will help you move forward.

You don’t have to talk to people who you know will judge you or who you know will say things like, let me swipe for you and that doesn’t feel supportive. Or people who will say things like, well, why don’t you go out with my cousin’s brother’s little nephew? Because I heard that he’s really cute and nice and you’re like, no, thank you.

Don’t even engage. You can just say, it’s going fine, pass the piece. You could also say something like, I’m. Really believing that what is meant for me will not pass me by. Pass the peace. Right, moveon.org.

You could also say something like, you know what? It’s going fine and I’m excited for 2025. Pass the peace. Practice being in the habit of protecting your peace with who you open up to about this.

I think you get to open up about your dating life to the right people and I want you to be discerning and center yourself and know who those right and wrong people are for this specific topic.

Now, if you experience judgment from someone or you get unsolicited advice about your love life that does not feel helpful, you have permission to leave the conversation. You have permission to viciously change the subject of like, they’re giving you unsolicited advice and be like, my God, wait, I love that brooch. That brooch is so beautiful.

You also have permission to just go to the bathroom. my God, I just got the urge to go to the bathroom, bye. Literally a bathroom break. is a great boundary. And then when you come back, they will probably moved on to something else.

Step number two is the self-care plan, right? How are you going to care for yourself actively, right? Do you have a therapy appointment scheduled? Are you in community with anybody who is going through this with you, who you can text?

I also love the book, Self-Care Activities for Women, 101 Practical Ways to Slow Down and Reconnect with Yourself by Dr. Cicely Horsham. breath weight and it’s such a good practical guide for like self care.

And lastly, listen to podcasts that make you feel belonging. Finally, during this holiday season, I want you to have a rock solid joy building plan. Joy is connective. Joy, your joy is important to prioritize.

So make a list of five things that you want to do this holiday season that would bring you unreasonable, giddy, playful, childlike amounts of joy. whether that is getting a gorgeous sparkly metallic watercolor set and going to town on some watercolor paper, I’m gonna do that.

Or it’s going to a really fancy hot chocolate shop and getting the fanciest hot chocolate in your town. Or inviting your friends over for a Lord of the Rings marathon.

What would bring you unreasonable amounts of joy this holiday season? Make a list of those five things and put them in your calendar. Prioritize yourself in your calendar this holiday season. Ask yourself the question, what do I want to do? Then do it, period.

What do I want to do? What do I think about this? This is the process of centering yourself in a way that will move you forward. Because I know that joy building is one of my components of an in-person dating plan.

You can make eye contact at joy building activities. You can say hello to cuties outside of your house just to build that thank you more please hope that there are people who exist. I don’t think you have to actively date this holiday season to be moving forward in your love life.

As a reminder, pass the P’s, move the conversation along. You do not owe anyone your story, both and release that self judgment as much as you possibly can with self compassion, acknowledge the desires that you have beneath the fears, and then build a plan with boundaries, self care, and that joy building. You’ve got this and I’ve got your back.