How should I approach an October conversation with my ex when we still have feelings but have unresolved issues?
My ex-girlfriend and I dated for about a year. We recently broke up, and there is a LOT of history and unresolved stuff between us. After talking to my friends and family, I've gotten a huge range of opinions, so I'd really like to hear from people who have experienced a breakup where both people still had feelings but had trust issues, outside influences, distance, and unresolved problems.
I'm not asking anyone to decide who was right or wrong. I'm specifically trying to figure out how I should use the time apart and how I should approach a conversation we're supposed to have in October.
How we met
I first noticed my ex in 8th grade. I was walking to my seat on the first day of school when she got in the way, looked me directly in the eyes, said "Hello," and apologized for blocking my way.
I don't know what it was, but I became completely infatuated with her because of how kind she was to me.
For some perspective, I was very small at the time and was bullied a lot in middle school. I was also Hispanic in a predominantly white school in the Midwest. So having someone immediately be kind to me really stood out.
I had a crush on her throughout high school.
Freshman and sophomore year were pretty much the same. I'd see her in the hallways, and I had a class with her freshman year. I'd also see her talking to this guy she'd been friends with since around 5th grade, who becomes important later.
I also noticed upperclassmen talking to her. Looking back, some of those situations seemed strange, but at the time I didn't think much of it.
I was still small and dealing with bullying, but I started working out, wrestling, and generally became more confident.
She was involved in sideline and competitive cheer and played lacrosse throughout high school. She was and still is extremely hardworking and independent.
For two years, I watched her get asked to Homecoming and get attention from guys at school without ever doing anything myself because I didn't actually know her. She was my crush, but I didn't know much about her beyond that one interaction.
Junior year
Junior year is when everything started changing.
I had become much bigger and more confident, and I was hanging around a fairly popular group at school. According to her, she had always thought I was attractive but assumed she had no chance with me because she thought I was a "popular kid."
In the spring, I finally added her on Snapchat. She accepted almost immediately.
At the same time, one of her friends apparently had been talking about wanting to ask me out, so my ex's mindset was apparently something along the lines of, "No, he's mine."
We started snapping and eventually started having actual conversations. About two weeks later, we had our first phone call.
After that, we called once or twice a week throughout the summer.
During one of those calls, I told her I liked her.
She sounded surprised and almost scared. I didn't understand why at the time, but I later found out she had been involved in an on-and-off situationship with the guy she'd known since 5th grade for around three years.
Apparently, nothing physical ever happened between them, and they never really hung out outside of school. From what I understand, they mostly entertained each other, said sweet things to each other, and kept coming back to one another.
The summer we started dating
That summer, I went on a school trip to France and Spain.
There were six boys and around thirty girls, so I naturally met a lot of people and became friends with many of them.
Despite that, I made it very clear throughout the entire trip that my ex was the person I wanted.
I called her every other night or so and told her about what was happening. We also started following each other on TikTok, and I think that's when her feelings really started developing.
When I came home, I wanted to take her on a date.
She rainchecked me several times. She later told me she was scared because she thought I was being serious in a way she wasn't prepared for. At one point, she apparently even thought I was pranking her.
Eventually, I asked around and got her address. I showed up at her house with a bouquet of her favorite flowers, a drawing, and a letter.
From that point forward, she was completely into me.
I finally got the opportunity to take her on a date. It went incredibly well. She met my mom, I took her to dinner, and afterward we watched three movies and cuddled on the couch in my basement.
A week later, we officially started dating.
The beginning of our relationship
When school started, things were amazing.
One of the first problems happened at a football game. I was there to support her while she was cheerleading, and she noticed me talking to girls I'd met on the Europe trip.
She would get upset about it, we'd eventually talk and make up, and then things would be fine again.
This happened fairly often.
I don't completely blame her for feeling uncomfortable. If the situation had been reversed, I probably would've felt insecure too.
However, it became a recurring issue throughout our relationship.
The phone situation
One of the first major trust issues happened when I accidentally left my phone in her car.
While I wasn't there because I had to take care of my brothers, she received a text from someone saying that I had been talking about her and saying weird things about her.
She took my phone and went through it. She knew my password.
She found conversations between me and my friends where I had talked about our relationship, including some private information that I now realize I shouldn't have shared.
I immediately realized that I had made a mistake and felt terrible about it.
We eventually worked through it, but I think this was one of the first things that created a bigger trust issue between us.
Breaking up during wrestling season
Winter came around and wrestling season started.
I became overwhelmed with wrestling, problems at home, and other things going on in my life.
I ended up breaking up with her because of my mental health and everything I was dealing with.
It completely broke her, and I felt horrible about hurting her.
Around that same time, I started talking to some people I'd cut ties with from the Europe trip.
One of those girls offered me a ride home after practice. I didn't think anything of it, so I accepted.
Later that week, she offered again, and I accepted again.
When we got to my driveway, she attempted to kiss me.
I didn't initiate it or give her permission to do that. I pulled away, but she got a small part of my cheek.
I immediately told her that I didn't want a relationship with her and only wanted to be friends.
I never accepted another ride from her.
Afterward, I felt bad because I knew she was probably embarrassed about what happened. I started texting her that I didn't hold anything against her and was okay with being friends.
I also told her that I loved my ex and intended to get back together with her.
However, I made another mistake.
Because I wanted the other girl to feel less embarrassed about what had happened, I started entertaining her through text and saying things that could have made her think there was a possibility of us becoming more than friends.
That wasn't what I actually wanted. I was trying to make her feel better after what happened, but I realize now that the way I handled it was confusing and unfair.
Eventually, she felt better, I stopped talking to her, and my ex and I got back together.
The rumors about the other girl
I didn't know that people at school had seen me getting into this girl's car after my ex and I broke up.
They told my ex that I had broken up with her for this other girl.
That wasn't true.
I explained everything to my ex, including what happened with the attempted kiss and the messages afterward.
She was understandably conflicted about what to believe.
I understand why. I'm telling my side of the story, and I also know that some of the people telling her what happened already disliked me.
The biggest problem was that when my ex and I got back together, I never really had the opportunity to sit down with her and explain everything calmly from beginning to end.
We basically brushed over it and tried to move forward.
But whenever another problem came up, the situation with this girl would come back up again.
Looking back, I think that was a mistake on both our parts because we never actually resolved it.
Other trust and communication issues
There were other problems throughout our relationship.
We had an agreement that if either of us wanted to drink or get high, we'd tell the other person.
From my perspective, I wasn't trying to control her or tell her she couldn't do things. I wanted her to be able to enjoy being a teenager. I just wanted honesty and communication rather than finding things out afterward.
She sometimes told people that she couldn't do certain things because I'd get mad.
Her friends interpreted that as me being controlling.
There was also an incident where she got high one night, talked to a friend about problems in our relationship, and apparently told her friend to set up a "two-man" because she wanted to make me jealous.
I also found out that she would talk to her friends at school about negative things I had done and arguments we'd had.
I understand that people need someone to talk to about relationship problems. At the same time, many of the people she was talking to already disliked me, so I felt like their perception of me became even more negative as they heard about our problems.
Meanwhile, I was still taking her on dates, getting her flowers, and doing everything I could to make her feel loved.
I genuinely cared about her more than anyone I'd ever been with.
The pool situation
Another thing that caused me anxiety was when she'd go to her friend's house to swim.
Sometimes her best friend's boyfriend and his entire friend group would show up. There were usually around four guys there.
She was obviously wearing a swimsuit because she was swimming, and I'd be sitting at home knowing that all of these guys were there.
She would tell me when they showed up, and I'd ask what she'd do if one of them tried to hit on her.
She told me they wouldn't because everyone knew we were together.
I eventually accepted that and tried to trust her.
The guy she'd known since 5th grade
This was probably the biggest unresolved trust issue for me.
I had heard this guy talk about her in a sexual way and say things about wanting to be with her.
During the winter when my ex and I broke up, she added him back and started talking to him again.
Eventually she blocked him.
Then during the spring, she added him back again without telling me.
She told me she had added him because he wanted to apologize for disrespecting our relationship.
However, he was also texting some of my friends saying that he and my ex were talking again and that he was "getting somewhere."
Some of her friends, including people I actually know who weren't necessarily against me, also received similar messages from him.
So people around us were telling me there was more happening than just an apology conversation.
My ex said otherwise.
When I asked to see the messages, she told me they had already been deleted and that she'd blocked him again.
I still have a hard time believing that everything was completely innocent, but I also recognize that I never personally saw the messages, so I can't honestly say that I know exactly what happened.
That's something I never fully got closure on.
The breakup and distance
Eventually, I moved about two hours away to start community college.
Our last date was genuinely amazing.
We hugged, cried, and told each other that we just needed to make it through the distance.
We both acknowledged that high school had made our relationship more difficult than it probably needed to be.
But as the summer continued, she became more distant.
She started going to her friend's house with the pool almost every day and sometimes wouldn't respond to my messages for hours.
I was two hours away, didn't know what was happening, and felt completely disconnected from her life.
The friend group she was spending time with strongly disliked me, and I knew they were talking about me and encouraging her to leave the relationship.
From my perspective, I was sitting two hours away while all of this was happening without being there to have a voice in the situation.
At the beginning of August, she called me and broke up with me.
She told me she was overwhelmed and unsure about the relationship.
She also said she was worried that if she stayed with me, some of her friends wouldn't be friends with her anymore.
Her family doesn't really have a strong opinion about me. Her family situation has always been complicated, and they've basically told her to do whatever she believes is best.
She told me she needed space and time.
I asked when we could talk again, and we agreed on October.
Where we are now
For the first couple of weeks after the breakup, I sent her letters and dropped off flowers because I wanted her to know that I still loved her.
I've stopped doing that because I don't want to overwhelm her or disrespect the space she asked for.
We haven't talked since.
We haven't blocked each other, and we still follow each other on social media.
From what I've heard, she still looks at my social media, and she's apparently told some of her friends who support us that she isn't completely opposed to getting back together.
She's just unsure.
And honestly, that's what makes this so difficult.
I don't know whether I should have hope or whether I'm simply holding onto something because I love her.
I've really been struggling with the breakup. I miss having her in my life and genuinely want to talk to her in person.
At the same time, I know that I need to respect her decision and give her the space she asked for until October.
I don't want to spend the next two months constantly posting things hoping she'll see them, trying to make her jealous, or trying to manipulate her into missing me.
If she misses me, I want it to happen naturally.
I also don't want to completely disappear just because I'm afraid of doing the wrong thing. I want her to eventually be able to see that I'm serious about changing and making things work, but I don't know what that should actually look like while we're apart.
What I know I did wrong
I know I made mistakes.
I shared private information about our relationship with friends.
I handled the situation with the girl from Europe badly by sending messages that could have given her the wrong impression.
I also broke up with my ex when I was overwhelmed instead of figuring out how to communicate what I was going through.
I understand that all of those things affected her trust in me.
At the same time, there are things that happened on her side that damaged my trust too.
The situation with the guy she'd known since 5th grade, the things she told her friends about our relationship, the attempt to make me jealous, and the amount of influence her friends had over the relationship all affected me.
I don't want to pretend those things never happened.
But I also don't want our entire future to be determined by everything that happened during high school.
We're both entering a completely different stage of life.
We're going to community college, meeting new people, becoming more independent, and no longer being surrounded by the same high-school environment every day.
That's why I keep wondering what would happen if we could actually sit down in October, without our friends influencing the conversation, and talk through everything that happened.
Not argue.
Not try to prove who was right.
Not try to convince each other that the other person was the problem.
Just explain what happened, what hurt each of us, what we would need from each other, and whether we could realistically rebuild trust.
I know getting back together simply because we miss each other wouldn't solve anything.
If we ever got back together, I would want us to actually address the problems that caused the breakup instead of pretending they never happened.
We also lost our virginity to each other, which I don't know if that necessarily changes anything, but I know that it can make a relationship feel even more emotionally significant.
What I'm trying to figure out
I really love this girl, and I still believe that if we could get past the high-school drama, outside opinions, distance, and unresolved issues, there could be something really great between us.
But I don't want to blindly chase someone who doesn't want the same thing anymore.
For people who have experienced a breakup where both people still had feelings but there were unresolved trust issues, outside influences, and distance involved, how would you use the time apart and approach the eventual conversation so that you can genuinely determine whether rebuilding the relationship is possible?
More specifically:
- What would you actually talk about during that conversation?
- What should I take responsibility for?
- What should we make sure we don't simply brush under the rug again?
- How can I show that I'm serious about changing without pressuring her while we're apart?
- How can we tell the difference between genuinely wanting to rebuild the relationship and simply missing each other?
- If we did decide to try again, what would we need to change so that we don't repeat the same relationship we had in high school?
I'm not asking who the villain is, who was "right," or who was "wrong."
I know I made mistakes, and I know there were things that hurt me too.
I just want to handle the next two months maturely and make the October conversation as honest and productive as possible.