Right person, wrong time? Or a lesson.

TLDR: Broke up with my girlfriend (we’ve dated twice before) after 10.5 months the second time. She said she still loves me and isn’t over the relationship, but her mental health is at an all-time low and long-distance is looming. She said a third try would be unhealthy, but we agreed to talk in a month (no promises). Feeling crushed, hollow, and overwhelmed — I miss her more than anything. I know I have unhealthy attachment patterns and parts of my life to improve, but I’m struggling to manage grief and hold hope lightly

We started dating halfway through her Sophomore year and my Junior year of high school, and we immediately fell very in love in the first few months (felt like love at first sight). I genuinely didn't realize I was capable of loving someone to that extent and it felt surreal. Some of the memories we made are ones I genuinely will carry with me for the rest of my life, and we would ruminate about how we were going to get married and live together. Looking back on it now, I can recognize that this was the honeymoon phase of our relationship, but I also think that great relationships should start out that way and build upon it once it wears off. Well after about 10.5 months these raw feelings had been fading, and it's worth mentioning I was her first boyfriend and she was my first girlfriend that was longer than a couple months. She brought up issues she had 2-3 weeks before the breakup, and I wasn't in a good place mentally and was nearing the college decisions phase in my senior year of high school (long distance was also a worry for her). Anyways I was too immature to make real changes and they could have partially been an excuse for fading feelings anyways, so she broke up with me in December 2024 and I was completely devastated and heartbroken.

The next few months were very hard for me and I would think of her every single day and my feelings were more real than ever. I began to slowly heal over the winter months and into early spring. Then I found out she had began a relationship with a new guy in March, and that felt like a gut punch and I was devastated again. I started thinking that if she had a new partner, why couldn't I have one? I began talking to a new girl a few weeks later, and we began dating that April. We both went to Prom with our partners, and things were okay with the new girl but I knew it would never compare to her. I know this was an extremely immature thing to do as I wasn't close to being over her and I was trying to fill the void with someone else, and this might have ended up causing more problems later down the line. Around April-May she realized she had made a mistake and began to miss me too, and reminisce about how happy she was with me. I also didn't get into a lot of the far away colleges I was originally hoping for, and I ended up committing to the University in my hometown. We had basically been in no contact for 5 months at that point (save for a few brief messages regarding me saying things about her when I was drunk, which she later told me was just a reason for her to reach out to me). On a random night in late May while we were both still dating our partners, she reached out to me and we began to text constantly, updating each other about everything and just talking. She shortly broke up with her boyfriend thereafter (she admitted it was a rebound and she felt they weren't compatible at all), and I needed to do the same but couldn't right away as my gf at the time was on a trip in Hawaii. Well we decided to meet up in person to discuss our feelings and what the plan of action was going to be, the hangout was surreal and the connection felt so alive and instant again (I was so happy, she was too, and I couldn't stop smiling). We both strictly agreed not to engage physically as that was cheating (even though I planned on breaking up with my gf), but our raw feelings were too strong and we made out, which is something that I really regret doing and she regrets as well, though it affected her much more than me which I'll explain.

I broke up with my gf a couple days later once she was back, and we started dating again. Things were going great for the first few weeks, summer began and she went on a 3 week trip to LA for an acting camp from June-July and I picked her up at the end of it, and we drove 8 hours back together over the course of two days and she stayed over at my grandma's house. We made long lists of dates we wanted to go on and endless movies to watch. Shortly after this word got out about us cheating, and she lost a few close friends over it (a couple of them were also going far away for college). This understandably devastated her, and was a big source of grief for her the next few months (the loss of one friend in particular was very hurtful to her).

The connection was definitely real again and was what brought us back together, however both of us were still young and definitely immature (I was naive to this and thought I had changed my habits from the first time, but I hadn't). The relationship slowly began to become more low-effort again, with her mental health not being good and mine not being the worst but I didn't have my life together at all (very disorganized in all other areas of my life, not as many friends/extensive social life as I would like, behind in college etc). The fall semester began for me, and months passed in our relationship. Come winter break that December, she went on a cruise trip to the Caribbean, and I began to notice her texting was off, and she seemed more distant. I began to anxiously reflect on the relationship and realized how low-effort things had become (we almost never went on dates and stayed at home a lot, even though we thoroughly enjoyed each other's company and the each other as people). I irresponsibly made a promise to her about how I was sorry that things had become so low effort, and that I wanted to change that (I truly did in the moment). She seemed very glad that I said this, and later told me that she told all of her friends how excited she was about that (hearing this crushes me now). Well my life was still disorganized and I was more behind in school than ever, I got fired from a job, and I fell from the level of my promise back down to the realistic floor of my habits. This definitely disappointed her, and she grew more distant through the month of January. I again consciously began trying to plan more dates and put more effort in towards the end of the month, and I remember this one specific hangout in late January where she was acting very off at the start, until we had a clear conversation (we hadn't exactly had one before) and she expressed everything she wanted to change, including effort and some other things. I agreed and was ready to do so, and after that conversation it seemed we were able to fully relax in each other's presence and enjoy our natural chemistry together. I was so happy spending time with her and it felt like a weight had been lifted off the relationship after addressing the issue, and I had so much hope for our future.

We hung out once more again briefly after that, and then she started acting really off. We didn't text for a few days (she left my last messages unread), and I dropped off flowers at her house and towards the end of the week brought up a fun date I had planned for us. I was extremely anxious that week because I knew how off things were and I was scared. Well at the end of the week she asked to meet up and chat, and we sat on a cliff next to the ocean and talked about it all. She began to cry and said she didn't think we were built for long distance, (we'd planned on doing it once she started college that fall throughout the relationship, but weren't super specific). It made sense she began to have doubts about it given the weight of the matter and that our relationship had become more low-effort than either of us would like, and she said she would talk to people such as her mom about it (who did LD 4 years with her dad) meaning that she wasn't fully decided on LD. I gave my take on it, which was that we needed to build a better relationship foundation the next few months to prepare for long distance and develop an overall healthier relationship, and that I believed we could do LD. We had a more clear, concrete conversation about how low-effort the relationship had became, issues she had with me looking up people on social media, taking her more seriously when she was being serious, and respecting her. She also told me about how her anxiety/depression (from a disease called PANS) had been worse than ever the past few months and that it was affecting all areas of her life. I listened to her and brought up a couple issues of my own, and once we were done she collapsed onto my lap, crying. I truly did feel ready to tackle these problems and grow together, and though my life was disorganized my mental health was improving and was decently stable, and I felt I could break my bad habits of the last few months.

I later learned she entered that conversation with the intent of breaking up, but she got too scared to. She then stated her will to go on a week break, but we were so happy hanging out together that night after the conversation we had (got dinner, went back to her place and cuddled) that she said "well I don't think I need to go on a break after all". Spending time with her continued to be amazing that night until we had a small falling out (she was looking at the progress of a female bodybuilder online and I said it was impressive, she took it the wrong way even though I didn't mean anything by it) and she felt I was already going back on what we said in the convo. She drove me home, but she didn't truly want to stop hanging out and admitted she was "supposed to be mad at me". We drove back up to her place, and cuddled affectionately (I couldn't stop telling her how much I loved her) and then I tucked her into bed. While we were cuddling, she expressed that she did still want to go on the break and changed her mind, but reassured me (and seemed genuine) that it wasn't about breaking up or making an immediate decision on long distance, rather to gather her own mental health and improve her well-being before she was ready to put in full effort we had talked about. I knew I was going to miss her that week but I was so happy after spending time with her and seemingly reinforcing our amazing connection that had been jeopardized.

Tuesday night of this week she ended the break early, she she did so because she missed me and wanted to make plans for Valentine's Day. We texted each other I love you and went to sleep. I was so happy to text her again and I missed her a lot too, and Thursday of that week she called me and wondered what I was up to, and asked to hangout. I couldn't make it, but I enjoyed just getting a phone call from her so much that my friends commented on how much I was smiling while on the phone.

Yesterday she asked to meet up (first time since break ended). Things went normally for ~30 mins and then she mentioned she might want to break up. We parked in a parking lot in her car, and she seemed torn about the matter and definitely still cared about the issues we mentioned in the conversation and seemed to give them some chance (she asked if I had made dinner reservations for Valentine's Day after I brought that up, I said I was going to ask her when we hung out if she could make it, which I was going to do). She expressed that she had given me enough chances to change and that I disappointed her, but this truly hurt because I had been grounding myself the past couple of weeks and especially during the break, and truly did feel like I was starting to get things together and that I could make the change. She said she had been more anxious and depressed than she had ever been the last few months, and that she was a mess. She also expressed that she couldn't do long distance, though given that she had expressed a desire to do this before and her being torn on the issue makes me think it could be different if she was healthy and gave our relationship a better chance. The Long Distance in question is also questionable, as some of her top schools are in the same state and were already some of my top transfer targets, as I plan on transferring after Sophomore year (meaning it could only be 1 school year of LD). I tried to do everything I could to save the relationship and said I wanted to stand by her and support her through this period, but her decision seemed increasingly more fixed. She also said she had some internal resentment towards me after what happened with losing some of her friends last summer. She said that overall, 35% of her decision was me not changing and 65% was her mental health, and that I shouldn't beat myself up over it (of course I will). She brought up how excited she was when I made that promise to her in December while on her trip, and that she was telling all of her friends this, but was disappointed when I didn't follow through in the next few weeks. That really crushed me as I again I did have dates planned and was actually beginning to follow through on my promise after grounding myself.

I realized I couldn't change her mind about the breakup in that moment and I had so many questions, so I asked about our future. I asked if she could see us working long-term if she had better mental health and if distance wasn't an issue, and she said yes. She do also say that she thought getting back other a third time would be unhealthy, though I think we got back together and broke up again because we did love each other but still weren’t ready to have a healthy relationship because of where both of us were and are in our lives. She also said how she wasn't over the relationship and loved me, and that it was extremely hard to make that decision and was heartbreaking for her. We both cried a ton during the course of the breakup. She repeatedly expressed how she needed space but wanted to breakup instead of taking a break this time. She also said she wasn't ready to completely lose me from her life and to fully cut off contact. I said it didn't feel like we were done and that it wasn't the end (I still think this because of how real our connection was even at the end), but she said she felt like we were finished (this was confusing because she gave mixed signals given the previous information). She wouldn't give a definite yes or no about whether there was a chance for us in the future, but she said she didn't want to get my hopes up. We agreed to have another in-person conversation after a month (and hopefully she will improve her mental health in this time), and will likely be NC until then.

So that's the whole story up until now, and I'm left feeling very heartbroken and confused. I felt very optimistic and reassured about rebuilding our relationship after recent conversations, and in recent moments I was certain our connection was still alive (she acknowledged this too) and that's why this breakup is so tough (1000% does not feel mutual as I want to make it work more than anything). I think ultimately, we are definitely very compatible people with a very high amount of natural chemistry and similar values, and that we have great potential to bring out the best in each other if healthy. I can recognize that we aren't in that original honeymoon phase from the beginning of our first relationship where we were madly in love, but I feel as if I've grown to know her completely as a person since then, and it makes me all the more wanting for us to grow together and for her to be my long term partner (I specifically reflected on this when we took the break recently, as I was having unsure feelings as well because of things becoming stagnant). I realized that the hole in my life and uncertainty wasn't coming from her not being right for me, but rather my life being disorganized and not put together. After reflecting on this, I felt so ready to build the relationship back with her and work towards our partnership potential (beyond pure chemistry and connection) that we weren't remotely close to. I always feel so happy and grateful to have her presence and be with her in the moment, and it seems like practical reasons such as LDR, and failing to maintain the relationship because of both of us not being in the best place in our lives (especially with her mental health) are the reasons for this breakup.

I'll respect NC until we have a conversation in a month, but I think I'm really just looking for advice on how to handle the whole matter. I know I need to use this as fuel and wake up call to become the best version of myself and reach my potential (which I've been far from the past few years), but I'm devastated and heartbroken and truly don't think this is the end for us, because of how alive the connection and love was even at the end. I know I can't torture myself with hypotheticals and wait for her, but I strongly feel that I would want her as my long term partner and can definitely see a future with her, and realistically could especially be ready to start over a healthy relationship with her once I have taken the time to get my life together. I especially think I'll always be tortured at the thought of what could have been, and how we found each other twice in our lives when neither of us had our lives together or were in a healthy state of mind. Should I move on and reject the possibility of this happening as a false hope, or should I not wait but always leave the door open if she makes a return? I just don't know what to do, I feel ready to accept this immediate breakup even though it's immensely painful, but not to move on for good and believe that this relationship was just something of the past, or a lesson to be learned. Could this be the right person, with wrong timing?

Thank you to anyone who read the whole thing, I really had to let it all out :).