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january 20, 2025

Jakey Jake,

I’m sorry it’s taken me so long to respond to you. My students are gearing up for their big winter concert, and a lot of my time has been focused on getting things ready. They’re all pissed at me because the concert is on Valentine’s Day, but there really was nothing I could do about it. There’s this huge track meet the night after that a majority of them will be going to, and the PTA is hosting its annual fundraiser the night before. Then with exams the following week…yeah. I never realized how much went into planning a band concert. I would just show up in my black pants and white blouse and not think much of it.

How are you? Have you fallen in love since we last wrote? If it makes you feel better, my love life is also non-existent. I haven’t bothered to try dating since I moved back to Mass. Cory really broke my heart, and if I’m being honest (because writing it in a letter seems far easier than saying it out loud), I don’t want to put my heart through the ringer like that again. It hurt too much. Why bother putting myself out there if I could end up hurt? Because I really would rather not feel this way.

A life of solitude is easy. I have good friends. I have a good job, despite the complaining teenagers. My apartment is really cozy, and I love living with Rachel. I have enough money to live the life I want to. I don’t have to think about sharing with someone else, or trying to fit them into this perfectly carved life I made. It’s easy and simple. I like easy and simple.

I’m re-reading your letter now, and it’s making me smile. I’m glad we both cherish that memory from the band bus. I’m also glad I didn’t totally embarrass myself with my music choices. I still listen to the Jonas Brothers all the time. They had such an epic comeback.

I have to admit, Jakey Jake, that writing letters to you has been my highlight during this bleak winter. They’re all saved in this sparkly box I still have left over from the holidays, sitting on my bookshelf next to my bed. When I’m feeling down, I just pop that glitter lid open and read them. It’s nice to think back on the memories that made me so happy, the memories that made me who I am.

I guess what I’m trying to say is, I like writing to you. I like having you in my life again.

Shelly

P.S. Kevin Costa was not a good kisser. A disappointment, actually.

january 22, 2025

Shelly,

For a moment there, I wondered if I screwed things up by admitting my feelings from all those years ago. I kept trying to recall what I wrote in that last letter and wondered if that would be the end of it. I’m really glad you like writing these, because I do as well. And I’m also relieved that I’m not the only one re-reading them over and over. You’re right, it’s nice to look back on happier times. Sometimes I wonder if I’m doing something wrong in my current life, because it certainly doesn’t feel as enjoyable as being a teenager. Most people I talk to say they hated their high school days, but I can’t relate. I really enjoyed them, and I’m nervous nothing will be as good ever again.

Do not worry, Shelly. I have not fallen in love in the last two weeks. That would probably take a miracle to happen. I honestly don’t think it’d be fair to start up a relationship with anyone right now, or probably for a very long time. I have too much baggage. Too much darkness. You talk about not wanting to share? I would hate to have to share that with another person, to let them in on something that feels ugly and scary and bleak. Yes, I’m better now, and being in therapy has helped a lot with getting through my day-to-day. But I can’t even fathom what it would be like willingly inviting someone into that.

You’re right. Sharing this in a letter does seem easier, for some reason. It’s easier to share what I’m feeling when it’s with a pen and a piece of paper. We’re still digging into my past at therapy, so we haven’t even discussed future relationships yet. You’re the first I’ve admitted this to.

Jake

P.S. I am thrilled to hear that Kevin Costa was a terrible kisser.

january 22, 2025

Shelly,

I know that I just wrote you a letter (that one is already in the mail), but after letting my thoughts really sit with me for a day, I’ve decided I have more to say.

I think you deserve to know what it means to truly feel loved. It sounds to me that this guy Cory was unable to give that to you, and I know it’s really scary to even fathom putting yourself out there again, but I think you deserve that. You deserve to be treated right, even if it means “putting your heart through the ringer” again. I haven’t really been in a serious relationship like you have, so hey, I may not be the best person for advice. But out of anyone in this world who deserves happiness, it’s you. You light up a room when you’re in it. You make people feel really loved. You skip classes and fly across the country to be there for a friend who couldn’t even say anything to you in return.

A life of solitude may be easier, but I’m not sure that is equivalent to a life of happiness.

And I want you to be happy, Shelly.

Jake

january 24, 2025

Jake,

But what if I am happy with my life? What if I would actually be happier being by myself, living the life that I want? With no one holding me back?

And what about you? Don’t you deserve happiness, too?

Shelly

january 26, 2025