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Dear Diary: Skittles, Cappuccinos, and Teenage Heartache

Kristen Season 1 Episode 4

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In this first Dear Diary segment, Kristen shares journal entries from her 16-year-old self, revisiting a short-lived high school crush full of notes, Skittles, and a sweet cappuccino moment. Through the nostalgia and drama, she reflects on how teenage insecurities—like the fear of rejection and caring too much about others’ opinions—still resonate today.

Join Kristen for laughs, insights, and a trip down memory lane as she explores how the past shapes us. Plus, share your own stories: What insecurities have stayed with you, and which ones have you overcome? Let’s talk about it!

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 So one of the new segments I want to do on the show is called Dear Diary.  for a little bit of context, I have always been really big into journaling. I always had notebooks. I was always journaling. I wrote some so many things and in doing some, , research for the podcast, I was like, you know what, let me go back and see things that I thought things that I wrote about,  Probably no surprise to anybody who knows me.

There was a lot of boy stuff. I was very into boys and it's a little depressing now because I look back and I'm like, Oh, I wonder what I was doing in this time of my life. And there's no real details about my life. It's just the boy that I liked, or if a boy liked me, or there was just, there was so much boy stuff.

There's been a little fun stuff as I've gone back and I read some of them. There's a little bit of drama, but there is actually some wisdom in them too. And some things that , I think is usable that I can share. I know that I've seen some people post,  Pictures of stuff from their previous journals or diaries.

I enjoy hearing people read about stuff just because it takes you back to that simpler time when really the only thing you had to care about was which boy liked you and if you were fighting with your friends or what was going on. So for this first, my dear diary segment, I found,  from October of 1999.

So for context, I was 16 at the time.  There's a few entries and it actually covers this whole story and I thought it would be fun just to read it out loud to you all and share it, like story time. So story time with Kristen with an E. Sunday, October 3rd, 1999.

Well, I had planned on starting this at the beginning of the school year, but I never really had anything worth writing about. Until now. Sometimes bad things happen and you can't talk about it to anyone, but you can write it. The same goes for good things. You can't keep it to yourself, but who can you tell?

Let me start at the beginning. On the first day of school, I got to see people I hadn't seen for three months. Some had changed, some hadn't. Seth got glasses. Jenny went to her natural hair color. Eric's voice got lower. I also, for some reason or another, actually noticed Eric. What a cutie! A few days later, after a soccer game, Eric came up to me to stick out his hand.

What? I asked. Shake my hand. Knowing how immature ninth grade boys can be, I was very cautious. What are you going to do? Nothing, he replied. Then, I thought maybe there was something on his hand. After making him wipe his hand on his pants, I finally did it. Thanks, he said as he walked away, leaving me in confusion.

The next day, I asked him what the point of it was. He explained it was a sign of friendship. Cool, huh? So every once in a while we just shake hands. It was our thing. It didn't last too long, but one day I was walking with him and we realized we sit in the same desk for our French classes. You could always write me a note and leave it in there, I had suggested.

He took me seriously, and the next afternoon, I found a note and a bag of Skittles. We passed notes for that desk, through that desk for a while. They were usually short and full of nothingness, but it gave us something to do. Through it all, I just thought of him as little Eric. I'd say stuff like, Aw, I just love Eric.

I thought he was absolutely, simply adorable. So it kind of surprised me how I reacted Wednesday morning when Kelly said, Johnny says Eric may ask you to do something soon. Suddenly, I saw him in a different light. I might actually say yes, I blurted out. But it was all just rumored and I didn't want to get my hopes up.

And Thursday came. I've got news for you, Kel told me. Eric liked me. That's the simple version of it all. He really, truly liked me. And the weird part was, I liked him too. I explained it to Kelly like this, I think in the back of my mind I liked him, I just didn't realize it until I found out he liked me.

So Cal told him I liked him too, and she says after that he never stopped smiling. Friday morning was pretty stressful, but the sweetest thing happened. Eric came into homeroom and handed me a cup of cappuccino. This is for you, he told me. He sat down and we talked for a bit. Later that day, he walked me to a few classes, even waited for me after tone chimes, and he's such a gentleman.

I don't know if this makes sense, but when he looks at me, I can see the care. I know he seriously cares about me. My friends won't disown me. Some people probably think I'm crazy. We'll both be teased a bit, but I really like him. Monday, October 5th, 1999. Something almost historic happened today. I asked a guy out.

Well, kinda. I invited Eric to the Great Adventure on Saturday. He thinks he can come, but he's gotta check with his parents and stuff. I have to know by Wednesday, so Some people seem to think he and I are already going out. We're just friends. Then there's Becky. Kristen, you're just gonna end up leading him on.

What if I actually like him? I asked. You do? She seemed nearly disgusted. It doesn't matter though. If I like him, I like him, and he likes me. It doesn't matter what anyone thinks. In fact, there's really only one thing that bothers me. I'm scared. Scared of getting too involved. Scared of getting hurt. I know every relationship eventually ends, and if I don't give too much of myself, I won't get hurt as badly, and I'm afraid of regretting it.

I don't regret going out with Nick or anything we did, whereas What's His Name, I totally regret it and I don't want that to happen again. I want to make sure I totally like Eric before any type of commitment. He seems to be really, well, at least quite a bit mature for his age. He's so sweet and I completely enjoy being with him.

I find myself smiling more and stupid stuff like that, you know? I just don't know why I like him so much. Or maybe I do. He's sweet, and nice, and cool, and extremely adorable. Today he said, I'm a nice guy. I like nice guys, I stated. Yeah, I'm a nice guy. Sigh. Maybe I'm not ready for a real relationship, but wow, I do like Eric.

Wednesday, October 6th, 1999. My happiness shouldn't depend on the status of a kind of relationship. It just shouldn't. But today was one of those days where you just want to cry till you feel better. So I did. But I don't. I feel worse. And the worst part is, I'm probably overreacting or something. It's about Eric.

I just feel like he doesn't like me. Maybe I was just a little crush for him. Over. Done with. Next. I mean, this morning things were fine, he told me I looked nice and walked with me down to the lunchroom, but after that, no note today, he barely talked to me, and I feel like maybe he doesn't want me around, like I get in the way, a bothersome pest, a cold that doesn't go away.

After chapel this afternoon, he didn't hold the door, he usually does. Thank you, I muttered as it closed. He apologized and seemed sorry, but the next door we came to, he said, I'll get it. But it didn't matter. I opened it on my own. If he doesn't like me anymore, I want him to tell me. He's free to like someone else.

We were never official or anything, and I'm not too involved that it would actually hurt. What am I talking about? I already am hurt. Maybe I wanted too much for a relationship with him to work out that those few sparks that were there just burned out, and I probably ended up looking really stupid cause I actually liked him and made it known that I liked him.

Now this. Tell me I'm overreacting. Just tell me I am. Please. FYI. He can't come Saturday. His parents have plans already. He seemed unhappy, but maybe it's just an act. Thursday, October 7th, 1999. When things go bad, they almost always get worse. Yes, Eric and I were just friends. Yes, he liked me and I liked him.

And yes, my paranoia was pretty correct. He wrote me a letter today and explained that he does like me. I am 16 and it just doesn't feel right. How'd I react? Yeah, I guess I was at least a little hurt. That's only natural. But it's not like I expected some serious relationship with him, you know? And I wasn't too involved that I lost any part of myself.

I also felt kind of stupid. I totally made it known that I did like him. People thought we were going out. Now this. But I know what went wrong. I did try to rush things. I found out he liked me and wanted to just dive right in. Can't do that. I have to test the water first. And if I'm not careful, I could fall in and drown.

I'm just scared. Afraid of guys. Maybe not the guys themselves, but the fear of getting hurt. Sometimes I just forget and think since everyone else is tied down, I need someone too. And that's sad. But through it all, this is actually very good. Cause Dale may still like me. He put his arm around me last night and rumor has it he's going to ask me out, but And with Eric out of the picture Then there's Josh.

I can't explain it, but we make eye and talk contact on the bus and neither one of us can look away. It's kinda nice. Except for when Sarah's on. She likes him a lot and I'm scared she thinks I flirt with him just to make her mad or something. I don't. Well, one week, my shortest kinder relationship ever.

Bye bye, Eric. Hello, who? The end.  So I thought that was such a fun little story. And it's almost like I am reading about somebody else because so much of that I don't remember and the details that I included were really kind of specific. The one thing I do remember, , in this kid, his name was Eric. I left out his last name for,  , privacy .

I remember specifically the day he came in and brought me a cappuccino. And this was back when McCafe wasn't a thing. McDonald's just had regular coffee and they had a cappuccino machine. And my friends and I would go to McDonald's and get the French vanilla cappuccinos.

They were delicious. And I swear I can't find one that tastes as good like the cappuccino machines at gas stations. It is not the same as what McDonald's French vanilla cappuccino us, but I remember that specific day when he brought it in I don't know what happened. The journal says that it had been a stressful morning or whatever I don't know, but I remember him coming in He sat at the desk in front of me because it was before it started and he gave it to me I just thought it was the sweetest thing.

I don't remember any of the rest of it really But, Eric, if you're out there, thank you very much for the cappuccino,  what I found interesting rereading that is that so many of the insecurities I still struggle with in my 40s is something that even when I was 16, I struggled with.

And it's that whole, not even just about boys, but do people like me? Do friends like me? Do I get too caught up in trying to be friends with someone and then it doesn't work out? It's because I read things wrong or Just , the fear of it, like the one line where I talk about how I'm scared of putting myself out there and getting hurt.

That's still something that I struggle with and I think that's something that lots of people struggle with and being able to get over that and being comfortable with yourself and not caring about what other people think and not caring about putting yourself out there. I mean, that was a part that I wrote about too, right?

Was saying that, , what people would think about it because he was two grades below being trans. Which interesting tidbit almost all of my serious boyfriends have been younger than I have My husband's a year younger than I am a college boyfriend was a year younger than I was and high school boyfriend was a year younger than I was so apparently that's my thing . The point is, it's interesting to see how insecurities and fears we have as children or as young adults can still stay with us if we don't have good ways to deal with it, get over it, and I don't know that I have the answers.

As I mentioned, this is something that I still struggle with. But I think that it's interesting to see where we've come from and learn from that. So, a fun little story from October of 1999. , I hope you enjoyed it as much as I did. Let me tell you, there are pages and pages and pages of material in these journals.

Every once in a while, we'll throw in one of these dear diary segments and see what we can learn from them. But what about you? What stories do you remember from high school? What insecurities did you have that you feel that you're still fighting with? Or what insecurities do you have that you learned to deal with and come through and you're on the other side of it and you can look back and be like, Oh yeah, that's where I was, but look where I am now.

So let me know, reach out, email me, Instagram and , let's talk about it.

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