Unsure of how my ex-boyfriend (35M) feels with these mixed signals and whether he's still interested

I’ve been dating this guy for about 8/9 months. We’re 9 years apart and I don’t notice the age difference. 34m, 25f. We get along like a house on fire, always laughing together. He tells me regularly ‘I laugh so much with you’, I know his friends, his family know about me but we haven’t been able to meet due to Covid. He used to call his parents every Sunday but since we’ve been dating, it’s become less and less. To me this is also a sign of being in a relationship with someone. We normally see each other a few times a week, sometimes less or more depending on our schedule. He invites me to all the ‘big’ things in his life, for example, we were going to go to his medical ball together (he would’ve been seen with me in front of other girls if there is anything nefarious). When we drive or hangout in different areas together, he likes to look up the prices of houses. He’s also said in front of me how cute kids are and that he can’t wait to do that one day. Signs to me he’s testing my reaction and seeing if I want that as well.

A few months into dating, he asked to make sure that we’re not seeing other people. He isn’t into casual sex and I think exclusivity is important to him. A few months ago I was anxious about what we were – he hadn’t asked me to be his girlfriend and I thought this is something that he would’ve wanted to do. He’s traditional, wanting something serious such as marriage/family. We had a few talks about the direction of our relationship, he said there were a few things he was a bit concerned about, a few things we maybe didn’t have in common (he’s very risk-averse and overthinks everything).

He’s studying so after that conversation he said he would decide at the end of his exams, his exams have finished now. He went away recently with some of his University friends, he was unsure of whether to go (seemed like he wanted to be with me, haha) and wanted to see me before he left. I’ve felt good about everything between us post-exams as I had a feeling he was going to slowly contact me less and less and try and see me less – due to his uncertainty.

One night on the phone, I told him that I wasn’t quite sure whether continuing to have sex with him was a wise idea as we aren’t boyfriend/girlfriend. He was confused that I said it was casual. I said ‘well, we aren’t in a relationship’ and he said ‘you are my girlfriend’ I’m certain he went onto say ’I thought we’ve known this since we started dating’ so I then asked him ‘well if I was to meet a new friend of yours that I haven’t met, would you introduce me as your girlfriend? And he said yes. Unfortunately, he has to repeat his exams so I may not be able to see him for a while, I do need to clarify that he actually meant this.I just wonder why he had this hesitancy a few times when we had the discussion a few months back though? There was even a point where I suggested we should end things because he wasn’t so sure and he agreed. Maybe this is natural though and a reflection of his risk-averse attitude about things. There were just some uncertainties on his part. He said he could’ve been overthinking it. As a result, it sort of made me more anxious and I suggested we should end it.

He said it’ll be good to have a proper chat about things as we’ve both been putting things off, as so he said.

I got to his house, he said yes I have been his girlfriend all along and he doesn’t know why I would think otherwise. He said that he feels it’s not going to work because of our age gap and he claims we’re very different people. I personally do not see this as I feel like we share the same values, we’re compatible in a lot of areas etc. He told me that he finds me beautiful, loves my sense of humour and that we get along and have fun together. I did mention that we handle conflict differently but our only arguments have been over text/call and since that’s such a poor form of communication – it’s hard to tell.

He started to cry (this is the most emotion I’ve seen from him), saying he won’t be able to cook me any more dinners and our memories shared together. He then went back and forth and said he doesn’t know if he’s making the right decision, that he will never find someone like me, I am out of his league etc. He said maybe he’s just one big idiot after all and he’s made a stupid decision. I was calm in my response and he said “why don’t you get angry? this is making it more difficult” in a somewhat cute way. He just kept saying that lately everything has been solidified in his brain that it’s probably the most responsible decision. He asked me if I thought he was being unreasonable.

Now I feel like since we’ve been arguing quite a bit the past few weeks and he’s been stressed, possibly his decision is skewed. I hadn’t seen him in 2 or 3 weeks due to exams and I asked whether maybe we just got cold feet because of us not seeing each other. I remember months ago he said he sometimes questions us in absence.

We spent over 4 hours talking and it was like he didn’t want me to leave nor did I. He then asked if we should go to dinner together. He finally walked me to my car and he couldn’t stop crying.

Something in me decided to message him the other morning after I left:Me – Morning 📷 I don’t know if messaging you is the best idea, but I hope you haven’t woken up too sad. If you ever want to catch up on neutral grounds, a coffee or lunch, don’t hesitate – I still consider you a friend. Even under these circumstances, it was nice to see you last night and I am saddened I won’t be able to have more of them with you. That’s all 📷Him – Morning! I was in two minds as to whether to message you with the same sentiment 📷 I feel very much the same. Like you say it’s always nice seeing you, and it’s hard for me to think we won’t be sharing more moments together. I really hope you’re feeling ok today 📷 Enjoy the rest of your weekend 📷Me – Aw, well if you’re keen to catch up in a week to come or a few months, let me know. I’m trying to not make this any harder for us but it is difficult. I didn’t react with anger because that’s genuinely not how I feel about us. I miss you, enjoy your morning eggs 📷Him – Will do 📷 miss you too, at least you can have your eggs with olive oil today 📷Me – These thoughts are best discussed in person but I’m not sure if that can happen and they’re weighing heavy on me. I do think we could work through the issues as I feel there are more positives than negatives. I am aware that the past few weeks have been pretty nasty for the both of us but I’ve been particularly harsh on you. If I don’t hear back from you, I will, of course, assume you do not feel the same way and will accept your decision.Him – I thought I did explain that although the last month or so has been really difficult, it hasn’t been the main reason why I reached the decision I did. Of course I’m always really happy to talk to you about anything though, so if you still want to talk things through naturally I’m happy to do that 📷He went onto say that he hates that he’s upset me and that it’s all really difficult for him but he thinks it’s all for the best.

We caught up and went to the beach together. We had a good time, he just feels at the moment he thinks it’s the best decision, although he isn’t fully confident he’s doing the right thing. He said maybe in a year it’ll make more sense and we realise we’re fit for each other. He said that he told his mother we broke up and she got really angry. Something was quite odd, he told me his friend (who I know) broke up with his girlfriend but they’re back together. We then went back to his for a cup of tea and we talked a bit more. He admitted that he does get in his head a lot and could be overthinking things. Said again that he’s scared he’s going to lose someone amazing but feels it’s the right decision right now. Again, I feel because I’ve been arguing with him over text lately and he feels overwhelmed. When I left, he said he wants to see me again in a week or 2.

We spoke on the phone the other day and I told him it’s really painful catching up with him and I don’t want to feel like an option to him or being left on the back burner, he said that wasn’t his intention and he would never do that as he has too much respect for me. He said it was hard catching up with me recently as well. He said he agreed to catching up because he felt like it was something I wanted. We spoke a bit more and he said that if he has a change of heart in the future, he won’t just sit on it. He’ll tell me. He told me he hopes I know how beautiful I actually am.

He ended up calling/messaging me over Christmas and NYE. I do feel like I am the one who predominately initiates contact with him first, I’ve been sending him sort of lengthy messages and he claims he’s overwhelmed by it. Recently we’ve been having an hour or so conversations when we usually would never have that as he was never one to speak on the phone. He expressed doubts about our break up as per usual and said he’s probably one big idiot after all. He told me he’s been on 2 dates with 2 girls as I asked, said he’s sort of interested but it hasn’t gone anywhere. I was quite upset and he assured me he wants to stay single for a while, he also said it’s not like he even wants a relationship with them. He said to give me some context that there were girls before we met that he was interested but it didn’t go anywhere. I was quite offended because he went on dates with girls that he basically broke up with me for. He broke up with me over an age gap but then went on dates with girls my age? Makes no sense. He said it’s all really regrettable and then told me that it’s not that he wants a relationship with these people and said they’re just friends he wanted to get to know better. He said he wishes I could see his phone.

He said over a month ago that a catch up would be good to clear the air. He also wouldn’t directly answer the question when I asked if he just sees me as a friend. I’ve decided to pull back, but it seems like he wants to catch up. At the start of this month, he offered to call about something, I think he was sort of surprised by that as I usually am jumping at any chance for us to speak on the phone. He sent me a message about the date/time tba (which I didn’t respond to) and then he sent me a follow up message about a week later saying “Morning, when works this week for you?” with a smiley face. He then said whenever is fine, to choose a day/evening and let him know. He then said he hopes my mother is doing okay. This was 2 weeks ago and I didn’t responded. He sent me another message 2 weeks later saying he hadn’t heard from me in a while, was wondering how I am and asked if my mother is okay. I replied and I was friendly, but brief. He replied and said a few things and then said ‘we never caught up in the end, let me know if you would still like to’ we talked a bit more and then I told him that I feel he just wants to catch up to free himself from guilt and that we can only catch up if we both feel it’s best for us to be together. He responded with saying that he understands and he didn’t think it would still be really difficult but he understands and there is a bit of truth in wanting to free himself but he thought it would be healthy in general. Apologised for the pain he’s caused me and wished me all the best. I told him that I just felt him talking about clearing the air was ominous and I just wanted to have dinner with him and not talk about us. He said that he understands how that could have caused it and apologies and said it’s the furthest from how he wanted to make me feel.

**TL;DR** ex-boyfriend broke up with me in November 2020. He cried a lot that day. He’s expressed doubt and says he’s probably one big idiot regarding his decision. We caught up a week after we broke up but I’ve decided to not see him for my own reasons. Lately he’s been initiating more contact and has been quite persistent in catching up with me but conditions the catch up as ‘clearing the air’. I was afraid he was just trying to free himself from guilt which I expressed to him and gave him the option of telling me if he still feels something. He then wished me all the best. Lately, I feel like we have been communicating better and we’re both not reacting as badly as we normally would.