--- title: "Meaning & Key Takeaway of: Dear Jessa, I’ve started this letter so…" description: "\"“Dear Jessa, I’ve started this letter so many times and I’ve never been able to finish it. So here goes again . . . I’m sorry. I’m sorry that Riley is ..." image: "https://sms4smile.com/quotes/i/cce/mila-gray-19868_bad-time_dear-jessa-i-ve-started-this-letter-so-m_3089571.jpg" --- # Dear Jessa, I’ve started this letter so many times and… ![“Dear Jessa, I’ve started this letter so many times and I’ve never been able to finish it. So here goes again . . . I’m sorry. I’m sorry that Riley is dead. I’m sorry for ignoring your emails and for not being there for you. I’m sorry I’ve hurt you. There isn’t a day that goes by that I don’t wish…” quote by Mila Gray](https://sms4smile.com/quotes/i/cce/mila-gray-19868_bad-time_dear-jessa-i-ve-started-this-letter-so-m_3089571.jpg) [Download](https://sms4smile.com/quotes/i/cce/mila-gray-19868_bad-time_dear-jessa-i-ve-started-this-letter-so-m_3089571.jpg) [Open image](https://sms4smile.com/quotes/i/cce/mila-gray-19868_bad-time_dear-jessa-i-ve-started-this-letter-so-m_3089571.jpg) > ““Dear Jessa, I’ve started this letter so many times and I’ve never been able to finish it. So here goes again . . . I’m sorry. I’m sorry that Riley is dead. I’m sorry for ignoring your emails and for not being there for you. I’m sorry I’ve hurt you. There isn’t a day that goes by that I don’t wish it had been me that died and not Riley. If I could go back in time and change everything I would. I’m sorry I left without a word. There’s no excuse for my behaviour but please know that it had nothing to do with you. I was a mess. I haven’t been able to talk to anyone for months. And I felt too guilty and didn’t know how to tell you the truth about what happened. I couldn’t bear the thought of you knowing. I got all your emails but I didn’t read them until last week. I couldn’t face it and I guess that makes me the biggest coward you’ll ever meet. I’m sorry. I’m sorry I never replied. You needed me and I wasn’t there for you. I don’t even know how to ask your forgiveness because I don’t deserve it. I’m just glad you’re doing better. I’m better too. I’ve started seeing a therapist – twice a week – you’d like her. She reminds me of Didi. I never thought I’d be the kind of guy who needed therapy, but they made it a condition of me keeping my job. She’s helped me a lot with getting the panic attacks under control. Working in a room the size of a janitor’s closet helps too – there aren’t too many surprises, only the occasional rogue paperclip. I asked for the posting. I have to thank your dad ironically. The demotion worked out. Kind of funny that I totally get where your father was coming from all those years. Looks like I’ll be spending the remainder of my marine career behind a desk, but I’m OK with that. I don’t know what else to say, Jessa. My therapist says I should just write down whatever comes into my head. So here goes. Here’s what’s in my head . . . I miss you. I love you. Even though I long ago gave up the right to any sort of claim over you, I can’t stop loving you. I won’t ever stop. You’re in my blood. You’re the only thing that got me through this, Jessa. Because even during the bad times, the worst times, the times I’d wake up in a cold sweat, my heart thumping, the times I’d think the only way out was by killing myself and just having it all go away, I’d think of you and it would pull me back out of whatever dark place I’d fallen into. You’re my light, Jessa. My north star. You asked me once to come back to you and I told you I always would. I’m working on it. It might take me a little while, and I know I have no right to ask you to wait for me after everything I’ve done, but I’m going to anyway because the truth is I don’t know how to live without you. I’ve tried and I can’t do it. So please, I’m asking you to wait for me. I’m going to come back to you. I promise. And I’m going to make things right. I’ll do whatever it takes. I’ll never stop trying for the rest of my life to make things right between us. I love you. Always. Kit”” [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) ## About This Quote This interpretation was drafted with AI assistance. It is one reading of the quote, not the author's own explanation. The writer expresses deep remorse for past neglect, guilt over a friend's death, and seeks forgiveness while acknowledging personal struggles and therapy progress **In simple terms:** Apology and guilt over neglect and loss Key Takeaway Seek forgiveness, continue therapy, rebuild trust Themes guilt apology healing friendship Mood sad reflective hopeful Type personal apology When to use this quote - personal apology - therapy sessions - rebuilding relationships Key Concepts psychology grief self‑compassion Questions to Reflect On - How can I demonstrate change beyond words? - What steps will rebuild trust? A Different Perspective The writer may not be ready to fully accept responsibility or may be seeking validation rather than genuine change ★ ★ ★ ★ ★ No ratings yet [Bad times](https://sms4smile.com/quotes/about/bad-times/) [Killing myself](https://sms4smile.com/quotes/about/killing-myself/) [Long ago](https://sms4smile.com/quotes/about/long-ago/) [North star](https://sms4smile.com/quotes/about/north-star/) [Panic attacks](https://sms4smile.com/quotes/about/panic-attacks/) [Time](https://sms4smile.com/quotes/about/time/) [Time and change](https://sms4smile.com/quotes/about/time-and-change/) ## Related quotes > [It all started in 2007 when I first saw you and I told my self I got to make this come true.your eyes got…](https://sms4smile.com/quotes/jas-rob/it-all-started-in-2007-when-i-first-saw-you-and-i-told-my-self-i-got/) Jas&rob > [“home, alone in my room, with the sounds of #2 and #5 trains rumbling in the distance, I started with a letter to myself.…](https://sms4smile.com/quotes/gabby-rivera/home-alone-in-my-room-with-the-sounds-of-2-and-5-trains-rumbling-in/) [Gabby Rivera](https://sms4smile.com/quotes/author/gabby-rivera/) > [“Does he call you his north star? 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Not…](https://sms4smile.com/quotes/mila-gray/death-is-the-one-great-certainty-in-life-that-s-what-my-dad-used-to/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) > [“I’ve never felt this way before, Jessa,’ he says. ‘I don’t want to fuck it up.”](https://sms4smile.com/quotes/mila-gray/i-ve-never-felt-this-way-before-jessa-he-says-i-don-t-want-to-fuck-it/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) > [“Are you mine?’ he murmurs. ‘Always,’ I answer as his lips find mine.”](https://sms4smile.com/quotes/mila-gray/are-you-mine-he-murmurs-always-i-answer-as-his-lips-find-mine/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) > [“I don’t believe you,’ he says. 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His eyes look smoky gray in the light from…](https://sms4smile.com/quotes/mila-gray/what-am-i-thinking-right-now-i-whisper-he-turns-his-head-to-face-me/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) > [“He wants me, but he’s also letting me know that he’s happy with just this, that this is enough for him.”](https://sms4smile.com/quotes/mila-gray/he-wants-me-but-he-s-also-letting-me-know-that-he-s-happy-with-just/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) > [“Because it wouldn’t have been fair to you,’ I say. ‘And then, selfishly, I knew that if I slept with you, then for the…](https://sms4smile.com/quotes/mila-gray/because-it-wouldn-t-have-been-fair-to-you-i-say-and-then-selfishly-i/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) > [“You've been waiting in the bushes for half an hour just to speak to me?" Kit shrugs. "I've done sniper training. I can sit…](https://sms4smile.com/quotes/mila-gray/you-ve-been-waiting-in-the-bushes-for-half-an-hour-just-to-speak-to/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) > [“What about you? Are you doing what you love?’He looks across at me before turning back to the road. ‘I was,’ he says. ‘And…](https://sms4smile.com/quotes/mila-gray/what-about-you-are-you-doing-what-you-love-he-looks-across-at-me/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) > [“For what It's worth," my dad says with a slight wince, "though I may have seen a little more of Walker then I'd ever…](https://sms4smile.com/quotes/mila-gray/for-what-it-s-worth-my-dad-says-with-a-slight-wince-though-i-may-have/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) > [“I'm good with my hands. Woodwork, metal work, engines...other things too.”](https://sms4smile.com/quotes/mila-gray/i-m-good-with-my-hands-woodwork-metal-work-engines-other-things-too/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) > [“I mean . . . Fuck, Jessa. If you ask me do I want you to be waiting for me the day I get…](https://sms4smile.com/quotes/mila-gray/i-mean-fuck-jessa-if-you-ask-me-do-i-want-you-to-be-waiting-for-me/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) > [“Why do you say that you love me?" He turns his head in my direction, still frowning. "Because I do," I stammer. "I love…](https://sms4smile.com/quotes/mila-gray/why-do-you-say-that-you-love-me-he-turns-his-head-in-my-direction/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) > [“Do you come here often?' I ask. As soon as the words are out of my mouth, I cringe. Way to go, Kit. Make…](https://sms4smile.com/quotes/mila-gray/do-you-come-here-often-i-ask-as-soon-as-the-words-are-out-of-my-mouth/) [Mila Gray](https://sms4smile.com/quotes/author/mila-gray/) [Explore all 32 Mila Gray quotes ](https://sms4smile.com/quotes/author/mila-gray/) ## More Bad time quotes > [Buddhism advises you not to implant feelings that you don’t really have or avoid feelings that you do have. If you are miserable you…](https://sms4smile.com/quotes/anonymous/buddhism-advises-you-not-to-implant-feelings-that-you-don-t-really/) [Anonymous](https://sms4smile.com/quotes/author/anonymous/) > [My friends and family are my support system. They tell me what I need to hear, not what I want to hear and they…](https://sms4smile.com/quotes/kelly-clarkson/my-friends-and-family-are-my-support-system-they-tell-me-what-i-need/) [Kelly Clarkson](https://sms4smile.com/quotes/author/kelly-clarkson/) > [Always respect, honour And Pray for those who helped you in your bad time. 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He died when I was 19, which is a bad time for your dad to die, because there's an awful lot of…](https://sms4smile.com/quotes/anonymous/my-dad-he-died-when-i-was-19-which-is-a-bad-time-for-your-dad-to-die/) [Anonymous](https://sms4smile.com/quotes/author/anonymous/) > [ “My dear friend, clear your mind of cant \[excessive thought\]. You may talk as other people do: you may say to a man, "Sir,… ](https://sms4smile.com/quotes/samuel-johnson/my-dear-friend-clear-your-mind-of-cant-excessive-thought-you-may-talk/) [Samuel Johnson](https://sms4smile.com/quotes/author/samuel-johnson/) Browse all 638 Bad time quotes ```json { "@context": "https://schema.org", "@graph": [ { "@type": "Quotation", "text": "“Dear Jessa, I’ve started this letter so many times and I’ve never been able to finish it. So here goes again . . . I’m sorry. I’m sorry that Riley is dead. I’m sorry for ignoring your emails and for not being there for you. I’m sorry I’ve hurt you. There isn’t a day that goes by that I don’t wish it had been me that died and not Riley. If I could go back in time and change everything I would. I’m sorry I left without a word. There’s no excuse for my behaviour but please know that it had nothing to do with you. I was a mess. I haven’t been able to talk to anyone for months. And I felt too guilty and didn’t know how to tell you the truth about what happened. I couldn’t bear the thought of you knowing. I got all your emails but I didn’t read them until last week. I couldn’t face it and I guess that makes me the biggest coward you’ll ever meet. I’m sorry. I’m sorry I never replied. You needed me and I wasn’t there for you. I don’t even know how to ask your forgiveness because I don’t deserve it. I’m just glad you’re doing better. I’m better too. I’ve started seeing a therapist – twice a week – you’d like her. She reminds me of Didi. I never thought I’d be the kind of guy who needed therapy, but they made it a condition of me keeping my job. She’s helped me a lot with getting the panic attacks under control. Working in a room the size of a janitor’s closet helps too – there aren’t too many surprises, only the occasional rogue paperclip. I asked for the posting. I have to thank your dad ironically. The demotion worked out. Kind of funny that I totally get where your father was coming from all those years. Looks like I’ll be spending the remainder of my marine career behind a desk, but I’m OK with that. I don’t know what else to say, Jessa. My therapist says I should just write down whatever comes into my head. So here goes. Here’s what’s in my head . . . I miss you. I love you. Even though I long ago gave up the right to any sort of claim over you, I can’t stop loving you. I won’t ever stop. You’re in my blood. You’re the only thing that got me through this, Jessa. Because even during the bad times, the worst times, the times I’d wake up in a cold sweat, my heart thumping, the times I’d think the only way out was by killing myself and just having it all go away, I’d think of you and it would pull me back out of whatever dark place I’d fallen into. You’re my light, Jessa. My north star. You asked me once to come back to you and I told you I always would. I’m working on it. It might take me a little while, and I know I have no right to ask you to wait for me after everything I’ve done, but I’m going to anyway because the truth is I don’t know how to live without you. I’ve tried and I can’t do it. So please, I’m asking you to wait for me. I’m going to come back to you. I promise. And I’m going to make things right. I’ll do whatever it takes. I’ll never stop trying for the rest of my life to make things right between us. I love you. Always. Kit”", "creator": { "@type": "Person", "name": "Mila Gray" }, "isPartOf": { "@id": "https://sms4smile.com/quotes/#website" }, "url": "https://sms4smile.com/quotes/mila-gray/dear-jessa-i-ve-started-this-letter-so-many-times-and-i-ve-never-been/", "about": { "@type": "Thing", "name": "Bad time" }, "@id": "https://sms4smile.com/quotes/mila-gray/dear-jessa-i-ve-started-this-letter-so-many-times-and-i-ve-never-been/#quotation", "image": { "@type": "ImageObject", "@id": "https://sms4smile.com/quotes/i/cce/mila-gray-19868_bad-time_dear-jessa-i-ve-started-this-letter-so-m_3089571.jpg", "contentUrl": "https://sms4smile.com/quotes/i/cce/mila-gray-19868_bad-time_dear-jessa-i-ve-started-this-letter-so-m_3089571.jpg", "url": "https://sms4smile.com/quotes/i/cce/mila-gray-19868_bad-time_dear-jessa-i-ve-started-this-letter-so-m_3089571.jpg", "width": 1080, "height": 1080, "caption": "“Dear Jessa, I’ve started this letter so many times and I’ve never been able to finish it. 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