Dear Diary,

Today is April 3, 2019. The mountains around me are whole kingdoms. As I ride in the passenger’s seat with my best friend, Jenny, I can’t imagine ever going back. The world suddenly looks bigger and life suddenly has felt so empty, until this very moment.

We’ve waited our whole lives to take this trip. So, I don’t know how to describe the way I feel now. Excitement? Nerves? Perhaps, both are true. All I know is I couldn’t be happier and more at peace.

Jenny and I’ve been best friends since the 2nd grade. I think she always liked me. I always liked her but was always too shy to tell her. Jenny’s a wonderful person. She’s both quiet and mysterious, and yet, wild and free at the same time. Her hair flows perfectly down her shoulders and her eyes light up the room. When she smiles, I swear Heaven is near.

I look over at her now in the pinkish-orange of the sunset and she looks radiant. She is kind and smart and smells like flowers. How did I get so lucky to be her best friend? Even after all these years.

Jenny and I never dated, although we’ve come close. She was always with someone else. The guys found her intriguing and fun to be around, but not as much as I have, I’m sure. She is gorgeous, so I have never been surprised that she got all the boys. I just wish that I could have been one of them. I hope there’s still time.

Anyway, I thought now would be a good time to give this diary writing thing a try. We’ll see how it goes. Until tomorrow. -Benny

Dear Diary,

Today is April 4. Jenny and I have been driving across the country since yesterday. We stopped and took a nap in the car but now I’m probably going to pass out again. But I thought I’d write first.

Anyway, the stars overhead are breathtaking. Like canopies of light draped over top of us, it’s perfect. It’s amazing how leaving the city, you can suddenly see the stars. Jenny seems to light up this ride, as well, and our conversations are the best. Sometimes they are lighthearted and playful and other times, we talk about the serious, deep stuff other people get bored with.

That’s probably why we’re so close. It’s never been hard to be around her. We can be ourselves and trust each other completely. I really can’t imagine my life without her.

We took this trip because we said as soon as we graduated college, we’d meet up and do it. You know, before life got too serious and stuff. I really wish we didn’t have to go back to the East Coast though. Boston is nice but not as nice as this.

Something new might just be what we need. What we need to finally start a relationship. I hope she can see me as more than a friend though. I really hope we can spark a romance and make some good memories in a memorable place. I love her so much.


Dear Diary,

Today is Day 3 of driving across the country to Colorado. Jenny and I have taken turns driving and now it’s my turn to rest. The sun is bright today but not as bright as my friend. When we get there, I hope I can show her a different side of me, a romantic side.

I never pursued her because she was always in other relationships. I never had a chance. But she’s finally single and we’re College graduates now! Real adults! So, I think it’s time. I think it’s time to show her I can be more than just her friend.

I like her a lot. I have since I was 7. I know she has liked me too. One time we almost kissed, before we were interrupted by her mom. That was in 10th grade and that was the only time. Another time, before we graduated high school, she told me she didn’t know how she could be in a different city and a different state than me.

So, like the sucker I am, I applied for College in Boston too. She was so happy she almost knocked me over hugging me. Then, there was the time she came to visit me on campus, Sophomore year. We were alone in my dorm and I wanted so badly to kiss her. I was about to, and she looked like she wanted it, when her roommate walked in.

So, I guess you can say that’s two times we almost kissed. Wait, I forgot about the end of Junior Year in college. I was visiting her that time. I wrote her a mushy gushy note thanking her for always being there for me and blah blah blah. Her eyes got teary and she hugged me so long and hard, I could barely breathe.

Dear Diary,

Today, April 6, 2019, we arrived at her friend, Doria’s house in Colorado. It’s a quaint place, very um- Mountain feel. Like a modernized log cabin, you could say. It’s nice. It has a hot tub and a front porch swing, and a fire pit in the back. I dig it.

Doria is friendly, very bubbly and outgoing, for sure. Her boyfriend, Cal, is the opposite. He’s a quiet guy, like me, but he seems very into the outdoors. I think I’ll get along well with him.

 But I’m not here for Cal. I have to find a way to win over the girl I’ve loved since before I could do multiplication. I don’t know what her type is though, even after all this time. She’s always dated all kinds of guys, maybe she doesn’t really know what she wants.

Anyway, I’m going to go to bed now and think about this time that I have with her. If there’s ever going to be a time to make a move, it’s now. It’s now or never. I’ve got to be fearless.



Today is April 7, 2019. Today was a great first day here. Jenny and I went rock-climbing with her friends, which was terrifying. I prefer writing about nature versus tackling it. But it’s okay. It stretched me out of my comfort zone, which is probably a good thing.

Anyway, Jenny laughed so hard. I wish I could just pause time and capture these moments. She looks so beautiful when she smiles. My heart melts every time. She was very touchy-feely today too. Maybe being around another couple inspired her? I didn’t mind though.

Nevertheless, we went to get ice cream afterward. It was some of the best ice cream I’ve honestly ever had. She had chocolate all over her face, like a little kid, and I couldn’t help but smile. She is wonderful and I’m so blessed to be here with her.

After ice cream, we went back and hung out by the firepit with her friends and some of their friends. It was a little chilly but the fire kept us warm. One guy there, Jamie, sang songs on his guitar and we all tried to follow along. Jenny looked so pretty.

I glanced over at her a few times across the fire. The fire seemed to shine a perfect glow on her face. I don’t know how this always happens but she is amazing. Maybe I say that too much but I don’t know what else to say. But being here is amazing too.

I love the mountains and the cool, fresh air. The sound of nature all around me comforts me in a way that the big city never has. I could stay here forever if she was with me. -Benny


Today, April 8th, was the best day of my life! I know that we’re only supposed to be here for a few months and so I wanted to not waste any more time. I forced myself to be courageous and finally tell her how I really feel. It was scary as hell but I did it!

We spent the day exploring the town and going into a lot of cool, local shops. She tried on some funny gear and we played with some random gadgets and trinkets and took pictures. Her friends couldn’t come, so it was just the two of us. Thank God.

We grabbed lunch at a local and tried some pretty amazing milkshakes together. After stuffing our faces, we found a park and collapsed on the ground. We talked for a couple hours and laughed over all the memories we have shared throughout the years.

Just when I thought it couldn’t be any better than that, she did the unimaginable and suddenly leaned over and kissed me!!!

I was so shocked but of course, I kissed her back. We did that for a few minutes before she pulled away and just looked in my eyes. She told me that she’d always loved me but didn’t realize how much she really did have feelings for me, until going through a lot of bad relationships. She told me that she had ignored the way she felt.

She didn’t think I felt the same way, or if I did, that she didn’t somehow deserve me. I was calm, cool, and collected and she was a wildcard. She told me that she always thought I would find someone better than her. She was surprised I never did. She said even when she was with someone else, sometimes she wished it was me instead. In a way, she may have used those guys, pretending they were me, trying to somehow get over her feelings towards me. All in all, she said she really just always had an excuse.

She was scared to tell me how she really felt because I was so incredible, better than all the guys she’d ever dated. She didn’t think I should be with her because I was much more of a man than she was a woman. I was almost speechless when she told me all of this.

She must’ve got embarrassed though because she suddenly jumped up and asked if I was ready to go. I wasn’t, but I wanted to respect her wishes. We walked a little more before heading back to meet up with her friends for dinner. She kept looking over and smiling. 

 After dinner, Doria suggested we all go into the hot tub and obviously, I loved that idea! Admittedly, I had wished it was just Jenny and me though. However, that wish came true when her friends retired for the evening. Jenny and I both purposefully stayed.

We both looked at each other and spoke at the same time. She told me she just wanted to apologize about earlier and that I should go ahead and speak. I decided to be brave. I scooted over next to her and put my arm around her and leaned down and gently kissed her.

Then, I looked into her big beautiful, brown eyes and told her never to apologize. I told her that I was SO happy about what had happened earlier. I told her that that had meant everything to me and she meant everything to me. I told her how I really felt. Finally.

Dear Diary,

Yesterday was AMAZING. Today was too. Last night, I told Jenny that I had loved her since we were kids. I had wanted to be her boyfriend my whole life but she’d never been available. She started crying and said how much better life would have been if that had been the case. I gently rubbed her hair and told her it was okay.

We had now, and that was what mattered. We hugged in the hot tub and there may have been some kissing involved. Oh, I also told her that she was worth my love and that I was in fact, the lucky one.

She cried some more and I did my very best to comfort her. We were very “affectionate” and I’ve never been so happy in my entire life! I have loved this girl forever and last night, she told me I better still want to be her boyfriend. Duh, I told her.

So, today, we got up and found each other. We haven’t stopped holding hands since. She’s not ashamed of me and I’m never going to be ashamed of her. Her friends seem to approve too, which is helpful but not necessarily mandatory. Nonetheless, she keeps kissing me and melting me every time. This trip will change my life. I just know it.

I’m going to take a break from writing for now because I think I’d rather just go out and live my life first. I’ll write about it later because I know there will be lots to write about. But for now, I am going to go live my story and hopefully, it will be one worth telling someday. I dedicate this journal and these stories to the girl I’ve always loved, Jenny Marie Montogomery. -Benny Brown

April 05, 2020 22:50

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