BobJone2000 Posted March 8 Share Posted March 8 Hey everyone, I recently went through a breakup with someone I really connected with. We were together for about five months, and while it wasn’t a long relationship, it was meaningful. We’re both in our early 30s and were dating with the intention of finding a life partner, which makes this breakup especially difficult. I’ve been struggling with regret over how things ended. A few years ago, I was engaged, and it ended horribly. After that, I dated a lot, but nothing ever felt quite right. I didn’t take meaningful steps to grow after my engagement ended and spent a while dating without real intention. But then, I met my ex, and our connection felt serendipitous. It was strong from the start—we both stopped seeing other people within just 1-2 dates. Everything felt serious and natural early on. We quickly introduced each other to our friends, which only reinforced how strong our connection felt. That’s part of what makes this breakup so difficult—I felt like I finally found something real again. We were exclusive and committed, and while we had differences in faith and background, we made it work. I told my family about her, but they weren’t supportive. I wasn’t fully open with her about how they felt—I gave vague answers instead of being direct. Looking back, I realize that my hesitation may have made her feel uncertain about our future. I cared for her deeply and showed it through acts of service, planning thoughtful dates, weekend trips, and always being reliable. But one thing I’ve realized is that I may not have been expressive enough. I don’t know if she ever truly realized how much I cared for her. I expressed love in my own ways, but I don’t think I made it clear enough through words or emotional vulnerability. We took our time before becoming intimate and built a strong connection early on, but over time, that connection faded—not due to conflict, but because I struggled with emotional vulnerability. We never fought or had any disagreements—not even a slight one. Everything always felt easy, but looking back, I realize we fell into a pattern of surface-level interactions rather than truly deepening our bond. Even our text messages started to feel platonic, shifting from meaningful conversations to daily updates about random things. In hindsight, I can see how that change may have contributed to the loss of romantic chemistry. One of my biggest regrets is that I became comfortable with the status quo and lost sight of the goal of marriage. It’s almost like I forgot how to be in an intentional relationship and fumbled my way through it instead of leading with clarity and purpose. I didn’t bring up important conversations about the future—things like financial goals, marriage timelines, and how we would navigate family expectations—and I regret not taking more initiative in discussing them. She also didn’t proactively bring them up, and in hindsight, I wish we had those conversations earlier. I wonder if we could have worked through these things together had they been addressed sooner. How the Breakup Happened She ended things recently, saying she felt like we made better friends than partners and that something was missing. However, she never gave specific reasons, and I didn’t push for them at the time. Most of what I’m writing here is based on my own self-reflection. She asked to meet in a public setting for the breakup after canceling our past two dates. The conversation was brief, which made it difficult to fully process in the moment. Sitting in the middle of a restaurant with strangers nearby, it wasn’t the right space to have an open and unfiltered discussion, and I struggled to take everything in. I shut down during the breakup and politely ended the conversation. One thing I later learned was that she had been feeling this way for about a month before the breakup. That was really confusing to me because just two weeks prior, on Valentine’s Day, she was on the verge of tears of happiness, telling me how easy everything was between us and how good she felt about our relationship. That same night, though, she also brought up my parents again. I reassured her with another vague answer, not wanting to ruin the moment. At the time, I didn’t think much of it, but looking back, I wonder if it was weighing on her more than she let on. I was completely shocked when she broke up with me just two weeks later. During the breakup, she also made a lighthearted comment referencing our differences in faith and background. At the time, I brushed it off, but in hindsight, I wonder if it was her way of subtly acknowledging that the family dynamic weighed on her more than she had expressed. One thing she did say was that if she were younger, she would have given things more time. That stuck with me because it made me wonder if this was really about us or more about her timeline for marriage and settling down. Where I Am Now We haven’t spoken since the breakup, and it has now been a little over a week of no contact. Everything still feels very raw. I’ve realized that the struggles I faced in this relationship—difficulty with emotional vulnerability, avoiding tough conversations, and hesitancy around family dynamics—are recurring patterns in my life. Because of that, I’ve scheduled my first therapy appointment to work through these issues and ensure I don’t repeat them in the future. More than anything, I feel like I left a lot unsaid. At the time, I was too shocked to fully express myself, and now I keep thinking about what I would have said if I had been in a better emotional state. I genuinely thought we would have a conversation about everything first, rather than her deciding to walk away. Looking back, I wonder if she felt I never reassured her enough about my ability to handle familial pressures and, in the end, chose to protect herself instead. At the same time, I worry that since she started feeling this way a month ago, she may have already emotionally processed the breakup while I am just now coming to terms with it. The Letter I Drafted I’ve written a letter because I don’t want to pressure her into an in-person meeting or disrupt her space, but there are things I don’t want to leave unsaid. It’s primarily for closure, but I won’t pretend that I wouldn’t be open to reconciliation if she were to change her mind. I care about her, and while I respect her decision, I feel like sharing my thoughts in a way that allows her to process them on her own is the right thing to do. For those who have been in similar situations: Did reaching out help you get closure, or did it make things harder? Have you ever reconciled with an ex? If so, what made it work? Would you respect hearing from an ex who has done self-reflection, or does silence say more? At this stage, does no contact give me a better chance of her reconsidering? Link to post Share on other sites
ShyViolet Posted March 9 Share Posted March 9 2 hours ago, BobJone2000 said: . I didn’t bring up important conversations about the future—things like financial goals, marriage timelines, and how we would navigate family expectations—and I regret not taking more initiative in discussing them. She also didn’t proactively bring them up, and in hindsight, I wish we had those conversations earlier. Whoa, this is way off the mark. You only dated for 5 months. I don't know where you are getting the idea that it would be appropriate to bring up the topics of financial planning and marriage earlier than 5 months of dating. It's not. Trying to rush things wouldn't have saved this relationship. The early months of dating are to get to know a person to see if you are compatible for a longer term relationship. It sounds like as she got to know you, she decided that she just wasn't that into you and didn't see a future with you. She doesn't have to give you the specific reasons. Sending her a letter won't change anything. 1 Link to post Share on other sites
Author BobJone2000 Posted March 9 Author Share Posted March 9 33 minutes ago, ShyViolet said: Whoa, this is way off the mark. You only dated for 5 months. I don't know where you are getting the idea that it would be appropriate to bring up the topics of financial planning and marriage earlier than 5 months of dating. It's not. Trying to rush things wouldn't have saved this relationship. The early months of dating are to get to know a person to see if you are compatible for a longer term relationship. It sounds like as she got to know you, she decided that she just wasn't that into you and didn't see a future with you. She doesn't have to give you the specific reasons. Sending her a letter won't change anything. This is someone who asked me about a prenup early on and how many children I planned to have. We are both on a different timeline. Link to post Share on other sites
basil67 Posted March 9 Share Posted March 9 4 hours ago, BobJone2000 said: This is someone who asked me about a prenup early on and how many children I planned to have. We are both on a different timeline. Your whole post was about how you could have been more open or didn't express yourself and wanting to write a letter about trying again. Now we find out that you're on a different timeline to her. This is mostly likely her dealbreaker.....why didn't you mention this? You say you're both in your early 30's. What's your timeline vs hers? Are you willing to change your timeline? Link to post Share on other sites
Gebidozo Posted March 9 Share Posted March 9 (edited) 7 hours ago, BobJone2000 said: This is someone who asked me about a prenup early on and how many children I planned to have. We are both on a different timeline. Big red flag. In the future, please be wary of such variant of lovebombing. More often than not, it is a symptom of deep insecurity and neediness. Edited March 9 by Gebidozo 1 Link to post Share on other sites
Author BobJone2000 Posted March 9 Author Share Posted March 9 7 hours ago, basil67 said: Your whole post was about how you could have been more open or didn't express yourself and wanting to write a letter about trying again. Now we find out that you're on a different timeline to her. This is mostly likely her dealbreaker.....why didn't you mention this? You say you're both in your early 30's. What's your timeline vs hers? Are you willing to change your timeline? Sorry. I meant to say that we both had similar timelines. Dating with intention and the goal of marriage. I never felt like she was moving too fast. Link to post Share on other sites
Gebidozo Posted March 9 Share Posted March 9 2 hours ago, BobJone2000 said: Sorry. I meant to say that we both had similar timelines. Dating with intention and the goal of marriage. I never felt like she was moving too fast. If asking for a prenup and discussing the amount of future children five months into a relationship is not too fast, then what is? This kind of crazy early overplanning almost never ends well. Overexcitement is bound to turn into disappointment. People burn out very fast with this kind of attitude. 1 Link to post Share on other sites
ShyViolet Posted March 10 Share Posted March 10 11 hours ago, Gebidozo said: If asking for a prenup and discussing the amount of future children five months into a relationship is not too fast, then what is? Not even five months into the relationship. The five month mark is when the relationship ended. So they were probably doing this like 2, 3, 4 months into dating. Which, OP, is not normal to do in a relationship, is absolutely rushing things and it usually does not end well. Your justification was that she was doing it too, so that makes it ok? Relationships that are rushed usually end just as fast as they began. It's not a smart thing to do. 1 Link to post Share on other sites
flitzanu Posted March 11 Share Posted March 11 99% of the time it is a waste to bother with a breakup letter. she is the one that left you, so she already knows that you want to stay together so you don't need to keep telling her. silence is not a way to "win someone back" either, your best bet for healing is to go no contact for YOU. write your letter, put it in an envelope and save it for yourself if you want, but there's nearly 0% chance she cares about your letter, and she's not the one that's going to give you closure, that needs to come from yourself accepting that she doesn't want to be with you. 3 Link to post Share on other sites
introverted1 Posted March 11 Share Posted March 11 You can't rush certain things. The sense I am getting is that because you are both in your 30s so you thought it would be a good idea to "date with intention," as you put it, which is not wrong in and of itself. The problem comes when you or she (or both) think you can rush learning about a partner in order to fit a timeline. You simply can't really know someone in 2, 3, 4 months. So rather than letting things unfold naturally, she pushed herself to make a decision about your suitability so as not to waste any more time. My guess is that she is going to be alone for a long time as it is next to impossible to find a lifetime partner in just a few months. If anything, I would say that your pace seems to have been more appropriate. In the early days, things should be light-hearted and fun. Sure, you can assess at the outset that you are both looking for the same things in life (marriage, family, whatever) in general terms, but to think that you should be discussing financial planning 4-5 months in is premature. Personally, I think you dodged a bullet here. And no, I wouldn't send the letter. 1 Link to post Share on other sites
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