Am I (31M) crazy for thinking there may be a shot at a relationship with an older serious (30F) relationship that we broke things off due to individual reasons and timing reasons that are now fixed but there is distance?

Am I (31M) crazy for thinking there may be a shot at a relationship with an older serious (30F) relationship that we broke off prior to her having personal issues?

Ok, so I really need someone to talk me out of taking a trip I may regret to see S(30F). To give the current context and there will be more current details later but in short a girl who I absolutely considered the one for me and I have talked on and off and are trying to plan a visit for me to come see her as she does not have the kind of job (chef) that permits a ton of vacation time. This is where my problem arises as I am almost uncomfortable visiting because I think deep down I still love what our relationship was and think it can be revived as there was no great conflict or issue between us that really ended it, here comes the context.

We dated much younger for a bit over two years, when we both were 18-20, we lived together at my apartment. I genuinely thought we would be married by now and I believe she did as well at that point (we literally almost got rings guys but I was a broke piece of crap), everything was wonderful. We eventually had small ups and downs but then it was like things changed out of no where, mood swings, odd issues. I wasn't sure what to make of it but without diving too deeply she helped me throughout the relationship at that point with issues I went through and I felt I very much wanted to be her rock and help her through whatever as going on, she learned she had serious issues with her thyroid. I was too attached and not mature enough and I as clearly an obstacle towards recovery at the time, I ended up transferring colleges and tried to never think of it again and start fresh after her therapist recommend she take a break from the relationship as it was so serious at the time.

She continued to have thyroid issues throughout my first semester during my transferring to another school and I helped her through as best I could from a distance and I do felt I helped her but I also felt by transferring I did damage as she lost a severe amount of weight, I was not sure if this was in combination with the thyroid but it was 50 lbs on a girl who was a healthy 130 and looked awesome. Aside from a drunken call or two initiated by either one of us, I had moved on. Dated a healthy amount, came back after graduation, got a job, then another and another and am still single and very successful, I own my own home and have a dog and my job is excellent, life is truly great.

BUT. About 7 months ago she begged me for a ride from the airport as she missed her flight and her mom asked her "Who the hell do you know willing to get you from Newark?! She called me, we had breakfast and caught up and it was fantastic, she is single as well I learned. But then things got trickier, she asked 2 weeks later for $300 as she was short for rent and didnt have anywhere else to turn, her mother is retired and her bother is not exactly a source of aid in that regard. They do have enough dough to lend her $300 though, but here she was begging me, she doesnt do drugs and has not seemed to change in that regard but I lent it to her, she paid me back and that issue it put to bed but it rubbed me the wrong and right way I guess? She trusts that I can help but also I am willing to give her money on whim which I dont want to be the norm or even more than a one time thing if we are just friends who occasionally speak across the country. We also have had several very long calls talking about how no one has been as good to the other dating wise and how we miss one another etc, to be clear she lives across the country from me now, we used to live in the same state but she moved. This is buried in case she uses reddit she will know in one fucking second who this is.

Ok since I am rambling back to my original point, she and I agreed for me to come out in like 8 weeks ish? Should I? I really have this feeling in my gut that I want to go there and see if its possible but part of me thinks save myself the trouble and money and text but that seems like a real shithead move after our history, this is driving me insane. Please frying pan level knock me into sense or tell me there may be a shot and I am not being used. Despite the money issue which I truly believe as valid, is this even a worthwhile idea, it feels so weird and I dont want to spring some sort of like ultimatum decision of like "I'm here and love you" shit on her, help me please reddit.

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tl;dr: Long loving history with a girl that ended due to medical issues and being young, possibility of coming back together? Should I poke the bear?

Submitted April 27, 2019 at 06:29AM

Am I (31M) crazy for thinking there may be a shot at a relationship with an older serious (30F) relationship that we broke off prior to her having personal issues?Ok, so I really need someone to talk me out of taking a trip I may regret to see S(30F). To give the current context and there will be more current details later but in short a girl who I absolutely considered the one for me and I have talked on and off and are trying to plan a visit for me to come see her as she does not have the kind of job (chef) that permits a ton of vacation time. This is where my problem arises as I am almost uncomfortable visiting because I think deep down I still love what our relationship was and think it can be revived as there was no great conflict or issue between us that really ended it, here comes the context.We dated much younger for a bit over two years, when we both were 18-20, we lived together at my apartment. I genuinely thought we would be married by now and I believe she did as well at that point (we literally almost got rings guys but I was a broke piece of crap), everything was wonderful. We eventually had small ups and downs but then it was like things changed out of no where, mood swings, odd issues. I wasn't sure what to make of it but without diving too deeply she helped me throughout the relationship at that point with issues I went through and I felt I very much wanted to be her rock and help her through whatever as going on, she learned she had serious issues with her thyroid. I was too attached and not mature enough and I as clearly an obstacle towards recovery at the time, I ended up transferring colleges and tried to never think of it again and start fresh after her therapist recommend she take a break from the relationship as it was so serious at the time.She continued to have thyroid issues throughout my first semester during my transferring to another school and I helped her through as best I could from a distance and I do felt I helped her but I also felt by transferring I did damage as she lost a severe amount of weight, I was not sure if this was in combination with the thyroid but it was 50 lbs on a girl who was a healthy 130 and looked awesome. Aside from a drunken call or two initiated by either one of us, I had moved on. Dated a healthy amount, came back after graduation, got a job, then another and another and am still single and very successful, I own my own home and have a dog and my job is excellent, life is truly great.BUT. About 7 months ago she begged me for a ride from the airport as she missed her flight and her mom asked her "Who the hell do you know willing to get you from Newark?! She called me, we had breakfast and caught up and it was fantastic, she is single as well I learned. But then things got trickier, she asked 2 weeks later for $300 as she was short for rent and didnt have anywhere else to turn, her mother is retired and her bother is not exactly a source of aid in that regard. They do have enough dough to lend her $300 though, but here she was begging me, she doesnt do drugs and has not seemed to change in that regard but I lent it to her, she paid me back and that issue it put to bed but it rubbed me the wrong and right way I guess? She trusts that I can help but also I am willing to give her money on whim which I dont want to be the norm or even more than a one time thing if we are just friends who occasionally speak across the country. We also have had several very long calls talking about how no one has been as good to the other dating wise and how we miss one another etc, to be clear she lives across the country from me now, we used to live in the same state but she moved. This is buried in case she uses reddit she will know in one fucking second who this is.Ok since I am rambling back to my original point, she and I agreed for me to come out in like 8 weeks ish? Should I? I really have this feeling in my gut that I want to go there and see if its possible but part of me thinks save myself the trouble and money and text but that seems like a real shithead move after our history, this is driving me insane. Please frying pan level knock me into sense or tell me there may be a shot and I am not being used. Despite the money issue which I truly believe as valid, is this even a worthwhile idea, it feels so weird and I dont want to spring some sort of like ultimatum decision of like "I'm here and love you" shit on her, help me please reddit.tl;dr: Long loving history with a girl that ended due to medical issues and being young, possibility of coming back together? Should I poke the bear?