This was something I posted about in r/relationships a little while back when it happened, but honestly my responses there were less than helpful. Here we go:

My current situation: I have been in two serious relationships. First one lasted 5.5 years, and second lasted almost exactly 2 years. The first one is the one in question here.

She and I were each other’s first everything. And I mean everything. She and I shared a very good emotional connection and she helped me mature as a person despite being 2 years younger than me when we started dating in high school.

About 3.5 years ago (December 2016) we mutually decided to break up because we were having issues mainly with emotional distancing and just generally not feeling like the other was….caring enough, for lack of a better term. We felt complacent, bored, etc. We both had our fair share of flaws. I felt like she wasn’t very exciting as a person anymore, I guess, and I had problems of my own, such as general emotional immaturity and just being overall dismissive as a person.

My 2 year relationship after that was a very important learning experience for me. The person I dated then was extremely toxic to me, especially when she was angry. I experienced pettiness on a level you would not believe. I was challenged to be the bigger and better person, to be the emotionally mature one and to control my emotions when all else seemed to fall apart. Thankfully I got out of that relationship in August of last year, and I have been very happy with myself since, despite the next story.

About 2 months out of my 2 year relationship, I hit up my first ex because I had had a very vivid dream about her. The dream was, in all essence, us getting back together and having a genuine conversation about it. Mind you, I had thought of her very minimally over the span of my 2 year relationship. That dream, though, made me realize something: I was HAPPY. It was like it made me realize something that I never knew I really wanted, that maybe I had been put through my last relationship in order to grow as a person and be the man she wanted and needed me to be back then. Plus, I was told by a friend that she had more or less ended her last relationship a month or so prior.

Side note: I am fully aware now of the mistake I made on this.

I decided to chat with her. I cordially invited her to coffee. She happily accepted, and we had a very nice talk. It was overall very relaxed, no strings attached, just catching each other up on what we went through the past 3 or so years. Eventually we landed on the relationship topic and she told me she was still seeing her partner of about 2 years. This broke me in ways that I am scared to think about. I played it off like it was ok, but following that event I fell into the deepest pit of anxiety. My thoughts included “Oh fuck, I missed my chance,” “What if this was just hopeless from the getgo?” and the like.

I hit her up again after that about 2 weeks later, following advice from my therapist to face these feelings of mine and learn from them. At the second outing I avoided any sort of attempt to get her to fall for me again, and more so just told her what I thought she should hear: that I had grown as a person in many ways and had learned a lot about what I was lacking when we broke up, and that I would have done a lot of things differently. She was very receptive to what I had to say. On the way out my last words to her were, “Regardless of what happens between us, just know that you set the benchmark for what I am looking for in a partner, and that I still care a great deal about you.” She was very touched by this. She told me that she truly appreciated the compliment, but that she could also not reciprocate those feelings I had (understandably at the time).

Fast forward to now, she has been single since December 2019 (she and I have the same friend group, and that was easy info to get). I hit her up again about 2 weeks ago asking if she wanted to get coffee and catch up again, but she is out of town until around early July. I was actually thankful to hear this, because it gives me much more time to mentally prepare.

Now, why am I doing this? Because I am feeling more complete and whole as a person than I ever have. Am I happy all the time and never lonely or sad? Of course not. But I am in a much better position to deal with my emotions now than ever. I am so confident in myself and I am so excited about life’s uncertainties. I am also eager to share that drive in my life with someone wonderful.

Was she perfect and treated me perfectly the whole time we were together? No. Not even close. Thankfully we never had a full on fight in our relationship, but we were both very young when we started dating and we were still figuring ourselves out. I can forgive a lot of what happened between us. Unlike my 2y relationship, she never really did or said anything that I would call unforgivable.

Even with the brief time that I was able to connect with her, I could tell she was still the type of person I would want to be with. Is she the ONLY one for me? No. But she’s the one I’m setting my sights on, this time with much more openness of the possibility of it not working out. If after these attempts it becomes clear that she really does not want to be with me, I can accept it.

As it stands now, we are on very good talking terms and have no negative feelings toward each other. Most baggage seems to have cleared.

My question is, what is the best route to approach this? If some of you think I should just not bother, that is fine, just tell me. However, I would appreciate any advise on how to follow through with this and make a good attempt of it.

On another side note: I have spent the past 7 or so months using dating apps but also spending time alone with myself, exercising, meditating, and generally working on myself. This isn’t something I’ve been mulling over or seething over for 7 months. I realized after the first breakdown that I had some serious work to do.

TLDR; trying to rekindle first relationship, we are on very good terms. I have attempted once to rekindle, fell short and fell into deep anxiety. Having worked on myself a lot and becoming more emotionally mature, I am looking for the best ways to approach this.

Thanks in advance!