Episode 391: The Magic of Halloween

In this episode of the Winey Palooza podcast, host Rebecca Greene, joined by co‑host Seth, celebrates Halloween by sharing her enthusiasm for the holiday and encouraging listeners to find joy in it. Rebecca outlines why Halloween is magical—its ability to let anyone become a character, the creativity of costumes, and the fun of decorating and pumpkin‑carving. She discusses family and friend collaborations on costumes, the importance of establishing traditions such as hosting a Halloween party, trick‑or‑treating, apple‑picking, and pumpkin patches. Practical "mom tips" are offered, including ordering costumes early, using disposable tablecloths, painting versus carving pumpkins, and safety logistics like meeting spots and phones for kids. Rebecca also addresses common criticisms of Halloween—candy over‑consumption, cost of costumes, and the holiday’s spooky meaning—offering counter‑arguments and encouraging a positive perspective. The episode closes with calls to action: listeners are invited to join Rebecca’s free newsletter, community groups, and to check out her blog, Linktree, and sponsor resources. Throughout, the tone remains informal, enthusiastic, and supportive, aiming to inspire families to embrace Halloween’s magic while providing concrete, actionable advice.
Chapters
Welcome to Winey Balooza Wednesday.
Wait, I'm trying to fix the wrong side of my hair.
There's a wrong side of your hair now? Your hair is fabulous, cut it out.
Mm, I'm fading into the sunset.
Wake up!
Whew, I even had some caffeine and it didn't do anything for me.
I'm sorry to hear that, let's make sure.
I better drink a lot of caffeine tomorrow. I mean, I have a lot of natural energy.
There you go.
I don't need any caffeine.
You are naturally caffeinated. All right, making sure everybody can hear us, we're good.
Okay, so it is October 30th. It is Wednesday, and I felt like, you know, there's lots of parenting and marriage topics. I mean, I have topics swirling in my brain, and I was like, how can you do anything that isn't Halloween this week when Halloween is tomorrow?
Halloween doesn't have to be scary.
Well, so I was gonna talk about scary things.
Boom!
I thought about, and I could do this next week because because it's not that far from Halloween. I was going to talk about scary thing— things in the theme of Halloween, but I decided to talk about the magic of Halloween because it's like one of my very favorite holidays.
Why do you like it so much?
I—
educate me.
I— okay, so I'm gonna go through my points. Here's what I want to say. If you love Halloween, then you're gonna love this episode. If you don't love Halloween, you still might learn something. I want you to stay with me. I want you to listen to my joy for it, and I want to challenge you to feel differently at the end of this. So if you don't like Halloween and you're listening to this and I change your mind at all, please reach out and tell me. I want to hear from you. And I want you to find reasons to like things. I want us to go through our day in our life looking for reasons to enjoy things.
You tell me that I should look for reasons to say yes to things.
Well, I love to say yes. I mean, we need to learn to say no. I'm not so good at that. We need to have good boundaries. That's a whole nother episode. It's a whole nother topic, I mean. So I love when he says yes. I love when I say yes, and I love to find joy in my days. And I was listening to a podcast this morning, and the lady was talking about how she finds joy in like little things like folding laundry, listening to a podcast, baking cookies. Like, I want us to find reasons to like things. So I'm gonna start by telling you that Halloween is like pumpkins and costumes and candy. Like, how could you not like Halloween? Um, do you realize how much your wife loves Halloween?
I'm looking around our house and yes, it's kind of clear.
So our house—
expanding our decorations.
So our house is—
you don't make any more room in the basement, but we get more decorations every year.
So our house is exploding with Halloween decorations. I did order more.
As soon as we're here tomorrow—
they arrived today.
Oh, you were saying you've ordered more and they got here. I thought you meant that you ordered more like today.
Well, in my defense, I did go to many stores, and my frustration with the stores— here is one of my mom tips: when you go to a store and you see something that you want, I want you to grab it. Because now that I want more stuff, not only is it all gone and picked over, the Halloween stuff is like gone, and now they're bringing in Christmas, and I'm like, people, it's not even Halloween.
Isn't there a Thanksgiving in between there somewhere too?
Like, why are you skipping a whole month? Nobody cares about Thanksgiving decorations. Like, maybe we want a pretty tablecloth and pretty napkins. Like, nobody cares about Thanksgiving decorations. But I care, I care about Halloween decorations, and I care about the fact that you've already removed them and are putting out Christmas stuff because I still want Halloween stuff.
All right, number points.
Okay, so I want you to grab stuff when you see it. So reason number 1 to love Halloween is that you can be anyone that you want to be. Did you dream of being a doctor? Guess what? You can dress up like one. Do you love Elle Woods from Legally Blonde? Oops, there goes my decorations. You didn't like what I said, huh? So if you love Elle Woods, dress up like her. Like, this is the time to embrace characters and have fun and do it up. I mean, What's better than that?
Got to be a Pink Lady from Grease.
So I've always wanted to be a Pink Lady.
I did not know about the secret fantasy.
Always wanted to be a Pink Lady.
Put your jacket on.
It's my sexy jacket. I literally put a jacket on.
That was your costume?
Not the best costume I've ever had, but my point is that you can be anyone that you want to be. And I'm going to take it a step—
socially acceptable to play Let's Pretend.
Yes. Play pretend, have fun, get into it with your kids, and collaborate with other people. Okay, so I wanted my friends to be Pink Ladies with me, but I'm slow and they already had costumes. So I want to tell you that September is a good month to start talking about Halloween, because if you want a group costume—
like, Ella's texting her friends going Let's all be blah blah blah, these characters from the show.
Yes, so collaborate and have fun with your friends. Now my family— Seth, you're gonna correct me if I'm wrong, okay? My family never tends to agree on a costume.
Oh, the 5 of us? Yeah, there's no way.
So we have never done like those family costumes.
Maybe when the kids were really little, I think we didn't have a choice.
I think that the trick to a family costume is that you do a family costume and you also let them get another costume that they—
because they're not all going to be in the same place on Halloween to wear it together anyway. Like, two of them are going their own other separate ways, right?
I mean, why not even just do it for a picture?
True, you could do that.
You could—
I would wear whatever you wanted on.
I feel like we did do it one year, but anyways, they were little, so we don't tend to agree. So I think that it's more of a friend thing. Like, my friends would have been Pink Ladies with me if I would have caught them in time. Um, Lily and her friends are all going as the same thing. So have fun with it and collaborate with your family and your friends. Okay, so we're gonna dress up and we're gonna be anything that we want to be, and we're going to collaborate, and we're going to get creative. Okay. What is better than getting your family's creative juices flowing? Okay, you get to pick creative costumes. You can even make your costume. You get to carve pumpkins, and you can do anything you want with your pumpkin. You can paint your pumpkin, you can carve your pumpkin, add some glitter to your pumpkin. You could do whatever you want, and you can put up decorations. I'm looking at my house. You can do your house can explode in Halloween. So what better time to get creative than Halloween? I mean, what's better than that?
I can't imagine, and I'm not gonna argue with you.
Do you— okay, so, so far, do you agree with any of this?
Sure, you are having a lot of fun. It is fun watching you have fun.
I am not—
but you drive the fun bus. Um, I would not be half as— Halloween would not be half as fun without your input. In creative direction. Okay, I love watching you amuse yourself.
Okay, so what about you though? You're not having fun, you're just having fun watching me. You're not actually having fun.
Well, to be fair, I haven't done anything. Yeah, okay, I wasn't here for carving pumpkins. You— I think I was at work or somewhere, or we were— I took a lot of Hamilton. I hung up a couple decorations. I was your ladder for a decoration or two. Um, I, I went as a greaser from Grease. That was amusing.
That was fun.
Um, you get into things more than I do, and I love that about you. So before me, I was so much more boring.
So tell me about Halloween before me.
I mean, if we're talking as a teenager, you know, a kid, I went trick-or-treating. But then did I do anything in the years from 22 to when I met you, to when we had kids? No, I mean, I wasn't going trick-or-treating as a 28-year-old, right?
No, right?
Yeah.
Were you going to like Halloween parties or anything?
I don't know that my friends were doing them in our late 20s, early 20s, late 20s.
Okay, so let's—
I mean, the last one we went to, it was your social work friends that when we were dating, remember?
Oh yes, that was so— what did I dress up as? Was that Red Riding Hood or something? I don't remember.
It was that long ago. It was like 20 years ago.
Oh my God, it was 20 years ago. That's crazy.
But now we host a Halloween party.
Yes, yes. So I want to talk about traditions as he, as he segues into the party.
Look at that.
So I want to challenge everyone to make some Halloween traditions. Because traditions is what it's all about. And then every year you look forward to the things that you do every year. So for me, what— I don't know how I started this, but I love it so much— is every year I host a Halloween party on Halloween, and the kids can invite whoever they want, and the house is open, and people come over. And Seth is gonna pick up a ton of food. Yeah, I ordered a ton of food. And we're gonna eat dinner and we're gonna eat snacks and we're gonna hang out and then we're gonna go trick-or-treating and then we're gonna come back and hang out.
Yes.
And it's always fun.
Yes.
And the—
it's a great party.
And the exciting thing about it is that there's no school the next day because everybody is usually rushing out by like 8, 9 o'clock because—
yeah, now we can party it up.
Everybody wants to get their kids to bed and this year there's no school the next day, so I'm so excited.
In our area, in our school district.
Our school district did something smart. So we host a Halloween party, we carve pumpkins, we pick costumes, we decorate. What else do we do? I'm trying to think of other traditions.
I think that's pretty— you sometimes, when the kids were younger, we would go apple picking or we would go to the pumpkin patch.
Well, so I do want to talk about that, but I also want to say that Lily and her friends also have the tradition of picking a costume together every year.
Yes.
So I hope that they do this for the next 6 years together, 5 years together.
Are they supposed to be trick-or-treating when they're 18?
When they're seniors and they're— they could do it, they could still dress up together.
Yes.
And go to a party or just pass out candy dressed up together. They could, they they could, they could all come here and hang out and pass out. We could all pass out candy in the driveway with a bonfire. Like, we can make, like, we can make new traditions. It doesn't have to always be trick-or-treating.
I love it.
But I'm going to say this as a mother: if big kids come trick-or-treating, who cares? Give them some candy. They're having fun. Embrace it. Don't be annoyed, just go with it, right? So for now, so our youngest is actually— Ella's trick-or-treating too.
Yes.
So Ella's 15, her and her friends I believe are trick-or-treating. Lily is 12, her and her friends are trick-or-treating. But there's going to come a day where our tradition of our big party and trick-or-treating is going to evolve into something different.
I love that you already have a plan.
I love— well, everybody has to like go with my plan. Everybody not might not agree Everybody might have different ideas. I'm just throwing it out there. But like my neighbors across the street, they set up this whole like station with a DJ, right? They play music and they—
I don't know that they got a DJ DJ.
No, they're the DJ.
Yeah, they have a laptop and a big amp. I've got amps from playing guitar. We could do that.
I'm just saying they set up this whole thing to pass out candy and it's awesome.
Yes, very, very creative.
And you know what I love? I love— if Kristen watches this, and I will tell her that I love this— every Halloween she always watches Harry Potter. Every year she watches the same movie. And I just think that traditions are just really good for us. Don't you think that?
Yes. And it's forward to them, and it's consistency.
It's like every, every holiday has their own traditions that we all look forward to. And we can make new ones and we can get rid of ones that aren't working. And you know, I'm thinking about Hanukkah and Seth is like, you don't need to get them a gift every night. And I'm like, well, I don't think it's about— it doesn't have to be a big gift.
We're going off on a tangent, just so you know.
I'm gonna get back. Okay. But I just like the tradition of giving them something every night.
I know you do.
So when he is away at college, maybe for— he might be—
we're talking about our son. You said he and you pointed in my direction.
When our son, yes, is away at college and it's Hanukkah, we are going to have to send him a package of 8 gifts.
I love that idea.
Okay, so moving on.
Yes.
Okay, so we have embraced being anyone that we want to be. We have collaborated with friends and family, with costumes if we want to do that. We have gotten creative and we have made some traditions. Okay, I want to throw in my mom tips that I forgot about.
Mom tips.
Okay, what tips did I forget? I think that I gave you the mom tips. Um, oh, I want to give you my pumpkin tip.
Pumpkin tip.
Okay, so two things about pumpkins. First of all, you weren't here for pumpkin carving.
No, Ella and I went to him.
Lily was so excited to pumpkin carve, and guess who carved her pumpkin?
A, that's super cute, and B, I'm sure you did all the work, right?
So I set up last year.
You, you normally make me do it. I just wasn't here.
I do, don't I?
Yes, I am normally the one who gets voluntold to carve the— to actually do the carving. They draw it and then I gotta cut it.
I was gonna say they come up with their ideas and then you end up carving, right?
You draw it because you are much better drawer than me, and then I do all the carving.
But I do suggest— my mother painted her pumpkin. If you don't want to deal with all the carving, paint your freaking pumpkin.
Yes.
And my other tip that most of you probably know is that I always use a throwaway tablecloth because man, are those pumpkins messy. And I just throw out the tablecloth. Do you know that?
I did not. That's very—
you should have seen my cleanup. It— you would have been so proud of me.
That's awesome.
Okay, just embrace it. Embrace the magic. Embrace Halloween. Embrace all of it. And I guess this stems from— I find that people are constantly telling me how much they don't like Halloween. Okay, so I'm going to tell you some of the things I've heard.
Okay, now you're going to play devil's advocate. All right, okay, I'm ready.
I have heard from the mothers who are annoyed by all the candy because they don't like their kids eating candy. Like, can we say bah humbug? Like, let your kids have some freaking candy. It's Halloween. Obviously we don't want them to throw up. I have been known to throw up. When I was little, I ate a bag of Hershey Kisses and I threw up.
But imagine anyone eating a whole bag of those would have that much salt.
I don't, I don't recommend binging the candy, which I have done. But I do—
to be fair, that was what, like 40 years ago? I think you're okay.
It was probably— yeah, it was probably exactly—
I haven't seen you do this in 20 years, so I, it's not— I never knew it happened. So you haven't done it?
I want to tell you the progress from when I was 8 years old. Okay, so 40 years later, I want to tell you about 40 years later. I'm sitting at the dinner table with Seth last night, and I said, can you pass me a Hershey Kiss? And I had one Hershey Kiss. I did.
It was tonight.
Oh, was that? I thought that was last night. Was that tonight?
No, when Max is like, come on, Dad, you should have eaten it and kissed her.
Yes, that was tonight.
That was a couple hours ago. It's all a blur.
I did not have the bag. I had one Hershey Kiss.
I'm proud of you.
Thank you very much.
Yes.
So I have heard mothers say that they don't like the meaning behind Halloween and what it means. Like, seriously?
Oh, we're scared. It's a time of day of the year when the spirit world barrier to the earth world is the thinnest and spirits cross over. And we're supposed to have the— we're supposed to stay up all night and scare the evil spirits away. Okay, All Hallows' Eve, right?
Right. So it's creepy, it's scary. They don't like the meaning behind it.
What about Casper the Friendly Ghost? Don't we want to welcome him in and give him some chocolate?
Oh my God, they don't like having to buy costumes. Costumes are overpriced. I've heard it all.
Get a sheet and cut a hole in it, be a ghost.
I mean, you could challenge your kid to make their own costume. I'll tell you what I like to do, and Seth might need to cover his ears. This is what I like to do. I like to go to Spirit, which we did not do. I like for Lily in particular to pick a costume. I don't care how much it costs. I just want to check it off the list. I want her to get something that she likes. I want to be done with it, and I don't want to make it. Some of you are creative goddesses and you can make a whole costume. I am not that person. We could maybe get my mother to do it, but I'm not gonna do it.
Good for you.
So, so I also want to give the tip that make your kids order costumes early. Do you know how many people have said to me, I hope it comes on time? Order it early. I said to all 3 of my kids, I said, I am not doing this last minute crap. Tell me what you want to be, let's order everything now. I don't want to deal with this. I got 2 out of 3 to listen.
It's progress.
So Max is a pain in the you know what. He— I think he has a Halloween party. I don't think he knows what he's being.
He's gonna have to come out of the closet.
Good Lord. So, so how did I do? If you don't like Halloween, did I move you at all? Did I give you any Halloween fun, spirit, joy? Did I change your mind at all? I just want to challenge everybody to find reasons to like things. I can't tell you how much I love Halloween. I am so excited for tomorrow. I hope that it goes well. I hope that your kids have fun. I hope that you have fun. I hope everybody's safe. I would say make a meeting spot location, like this is where we're going to meet if you get lost. I would like my children to bring their phones with them. My kids are of the age where they could call me if we get disconnected. Um, what's the word I'm looking for?
Separated.
Thank you. Oh my gosh. You can tell I'm tired. So I hope that you have a wonderful Halloween. I would love to hear what you love about Halloween. I would love to hear if I helped at all. I hope that I did. And I would love to tell you that— let's make sure I get all three of her names because I forgot the last one— Jenny Ketchum Crooks is on the podcast on Friday, and we talked all about the digital world You're gonna love her. You're gonna love her pointers. I loved talking to her and learning from her, so that'll be released on Friday. If you are not part of the Winey Clues a Mom group, please come find me. It's a free supportive community. You do not have to be a mom to join it. You just have to want some support. And I'm starting a new challenge on Friday, so that will be fun, and I'll give away prizes, and we talk about challenges and successes and advice. And what else, Seth?
Go to whinybalooza.com, find the Linktree with all of Rebecca's resources. Listen, rate, review, subscribe, and share the podcast and this vlog. And then go sign up for her free 3 times a week newsletter that is growing like crazy because people are sharing it. So be part of the in-crowd and join the Whiny Balooza Parenting and Marriage Newsletter too.
And the newsletter is free.
It's all free.
Everything is free. I'm giving away everything for free.
You have advertisers and sponsors that are paying for it.
I'm totally kidding. There was something that you said though before the newsletter—
podcast, podcast, vlog, like, rate, review, subscribe, share, Linktree, winyepalooza.com.
Oh my gosh, I don't remember what I wanted to say, but Halloween is fabulous. I, I know what I was gonna say. If you go to winyepalooza.com This— every topic every week is written as a blog. So there is a blog of how— you can read it— la la la la la. The Magic of Halloween is also a blog that you can go read and enjoy. And I would love you to share this with somebody who loves Halloween or somebody that you would love to get to love Halloween. So we will be back next week with a new topic.
Happy Winey Palooza Wednesday.
Thank you for tuning in to the Winey Palooza podcast. If you like what you heard, please be sure to subscribe so you never miss an episode. While you are there, leave a review. I love to hear your feedback. Thank you so much for listening. Until next time.
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