Stuck in confusion with a long-lost friend

[Repentant]

New here, and this may be a longer one for context, so please let me know if there's anything I should change. Guy (me) and girl (her), both in our mid 30s.

A little over a month and a half ago, I got a connection request from my high-school best friend and first crush, with whom I haven't spoken in well over a decade and a half. She popped up out of nowhere, stating her reasons being that she dreamt repeatedly that I wasn't talking to her. Initially, I was reticent, as it felt weird to be getting anything from her after such a long time, but went with it Polite and Friendly (as I always do).

As a bit of historical context, we were very close in high-school, spending at least every other day together even outside of classes. I'd confessed to her back then that I was developing feelings, but she had a boyfriend at the time, so I didn't press. She also seemed to just kinda' avoid the subject (responding with abstract stuff like "what is love, really?" and such). We maintained the friendship, but she also became open to small bids of affection: caressing/holding her hand, pecking her on the cheek, hugs, etc. 

Returning to the situation at hand, I started falling for her after about a week of chatting. I panicked when I realised this, as I remembered the first episode of Carrying The Bag Alone and didn't want to do it anymore. I waited another week to be sure of what was happening, and then sent her a sincere "goodbye" letter (more like a very long text, but structured as such), laying out things clearly and honestly, the full extent (including the fact that I was falling hard for her again). She replied saying that she doesn't want me to get hurt, but that she started looking forward to our conversations and wouldn't want to lose this, that I'm most certainly not indifferent to her, but that she's having a rough time figuring her feelings out. I accepted to continue both because I understood that the door wasn't closed and that she kinda' needed the interaction. She also said she was looking forward to meeting up in a month's time from then, when she'd drop in our old country for a bit.

This went on for a couple of weeks, but things started getting harder and harder to manage on my end - I started spiraling out of a certainty that there's no way things could work out (to add to everything, she has a LDR boyfriend with whom "it's been over for a while now," but she's scared of hurting him, so is procrastinating the break-up; to add to this, we're in two different countries - I wouldn't have a problem trying to move, but I'd most certainly not think of it unless there was an actual relationship going). I was honest with her throughout, both about the affections and this spiraling. She, again, responded well to bids, with things getting even "lovey-dovey" between us (things like "I'm sorry, I'm getting the strong urge to kiss you right now" / "I'd let you," a lotta heart and love-y emojis, "good morning" texts, etc.) and shared a lot of her personal life with me. 

However, things turned sour one evening when I was going through a rough spot with the spiraling. I'd apologised if my texting was off preemptively, stating only that I was having a rough time. She started probing and I was honest in my replies, but always made a point of formulating everything as "this is my problem to deal with, not your fault or responsibility." As the conversation progressed and questions kept coming, I got into the minutiae of my destabilisation: that I saw no hope for success, that things are only getting more and more defined within me as time passes, which made everything worse, and that it's been so long since I've seen a clear-ish trajectory in life, that the building frustration around that didn't help, either. At this point, I could tell something was off - she was spamming short replies instead of formulating longer ideas, as she used to. I didn't understand what or why, so thinking that maybe the subject was overwhelming, I asked her if she still wanted to chat knowing what she knows. She said I was guilt-tripping her and forcing her to define a relationship. I tried to clarify (again) that it was most certainly not my intention, nor what I thought about her or the situation, but the conversation became so hectic, that my replies were getting lost in the deluge and her flame kept being fanned. We ended the conversation with quite a bit of tension, so the next day I decided it'd be best to follow through with my initial plan for both our sakes: I sent another "goodbye" letter, again, with nothing but openness and genuine love.

I didn't expect a reply this time, but got one toward the evening: she continued based on her idea that I was guilt-tripping her and pressuring into defining a relationship, that I was accusing her of hidden intent by stating that I don't understand why she reached out (and that's literally all I said and meant, the dream thing made no sense to me), that "if I really wanted to know" (with that typical venom) she saw a lot of potential in me, but wanted to get to know me a bit better again, that I'll always be dear to her, but given the pressure she felt, she couldn't do this anymore, that she regretted contacting me given that things turned out this way, etc. I will admit, at this point I started feeling a bit offended, so I sent a reply in which I dove into reading comprehension - I approached every single point she mentioned and went through what I said, demonstrating that what she got was in no way related to any of my intentions. The thing turned into an argument, with her every subsequent reply being like "oh... but then what about the other thing?" This went on for about an hour, with my reply being the last: I tried to find milder synonyms for "dating" in order to clarify the only thing I would have wished would happen between us romantically (it's been 15 years, I may be romantic, but I'm not an idiot to believe things haven't changed for both of us), that I felt deeply uncomfortable with her still having a boyfriend and us going lovey-dovey, that it was confusing, and finally left it open by saying "I have no idea what I'm doing, we can still talk if you'd like."

Nothing but silence from her for two weeks, disappeared mid conversation. I didn't want to press or pressure, so I said nothing. Finally after two weeks, I reached out with a "hey, I don't understand where we left it off, I thought I'd regret it more if I didn't send you this message and left the huge 'what if' in my lap without a conclusion, you don't even have to reply, I'll take silence as an answer." I waited for about 6-7 hours, then sent her a "Hint taken, I'm sorry things ended up like this. Take care of yourself, I won't bother you again." It was then that she replied, saying that she was sorry, that her new medication had some side-effects that made her feel she didn't have the headspace to deal with more than one thing at a time, that she didn't want it to end in silence, and she'll reach out whenever. I didn't press, said I'm here to help if she feels I can, and told her to drop a line whenever, no pressure.

Another week passes and I receive a text from her asking if I'd like to meet up for a coffee, as she had some layover time in my city the next day. I'd initially felt reticence in accepting, as it was just a horrible situation for me at that point and I had started the "moving on" process as I was sure I'd never hear from her again (deleted everything, removed her from socials, etc.), but I did it anyway. The meet-up was fine, although a bit low on energy. We got along fine, I apologised for making her feel the way she did and tried to clarify that it was 100% not my desire, nor what I expected from her, she accepted and agreed that it was a misunderstanding. I told her I'd hug her, and she launched into a hug without hesitation. It went on for a couple of hours, after which we parted ways with the understanding that our interaction continues and we'll try to move on together. 

This happened last Thursday. Since then, communication has been sparse and significantly reduced - she hasn't initiated, hasn't asked follow-up questions when I initiated, and the level of detail is somewhat reduced. We talked twice, once briefly after the meet-up, and once briefly yesterday, when I dropped a "how's it going." Now, I'm not assuming it has solely to do with me, as she's still regulating her medication and is exhausted, plus she had a busy weekend. But something most definitely feels off.

So, I guess my question is what can I/should I do from here? My bottom line is that, although the past month has made me cautious around her and her behaviour, I still do feel a lot for her and am open to more than friendship. But I'm reticent bordering on fearful of even approaching these subjects with her again, because I don't want her to get the wrong idea again.

[Sanch62]

You're reverting to your adolescence and playing that out all over again in your own head. You're drilling yourself into a hole based on what, text messages? Your drama bypasses the point that this woman has a BF. She's just too self-involved to break up with him.

Instead of doing this kind of grind, why not tell her you enjoyed seeing her again, and if she ever finds herself free and clear of a BF and willing to invest in a relationship with you, you'd love to hear from her. Short of that, you wish her the best.

Then get on with life. If she's ever serious enough, she'll have no trouble catching up with you, and she'll make sure you're the first to know. Otherwise, WTH are you doing?

Edited September 22 by Sanch62

[Repentant]

Thanks so much for your reply! 

Honestly, this is exactly what I was thinking from the start, and 90% of why this was my first reaction when it became clear what was happening to me. I genuinely didn't want to do the dance all over again. Plus I was sure the uncertainty and rough aspects of this interaction (i.e. distance, relationship status, etc.) would chip away at me, and they did.

It's just that, right now, I'm scared of even touching the subject. I'm not kidding, I don't want another blow-out, or her thinking that I'm trying to pressure her into anything (and I still don't understand how my backing off is pressuring her into anything, but anyway).

If you don't mind my asking, if I were to approach backing off again, should I give it more time before I do? I still feel that things are off between us (maybe it's just me that's off, not denying that possibility as I'm pretty emotionally compromised right now) and I genuinely don't want to add to her stuff...

[flitzanu]

i think you need to stop verablizing all of this to her.  

you told her how you feel, and she's all but said that she's not going to date you.  at this point, if it's not a "yes" it is a "no" plain as that.

plus, she has a boyfriend.

if you decide you don't want to talk to her anymore you don't have to write a romance breakup letter, just stop talking to her.  tell her that you're not interested in just being friends and wish her the best and move on.

 

 

[Repentant]

Thanks for your reply! 

Honestly, I'm not even expecting to date her at this point - I may be open, but that reticence of approaching these subjects ever again is stronger. It's felt like a minefield so far, and I'm done trying to navigate those.

The only issue I have at this moment is that I'm unsure how to go about it. I'm completely overthinking it, I know, but I can't shake feeling like it's too abrupt given what has happened in the past week (her reaching out again and meeting up). I'm not taking this as a hint for anything more, btw, just saying - we just recently agreed that the interaction'd continue, and just days later I'm popping a "y'know what? actually no, buh-bye!"

 

[Sanch62]

16 hours ago, Repentant said:

If you don't mind my asking, if I were to approach backing off again, should I give it more time before I do? I still feel that things are off between us (maybe it's just me that's off, not denying that possibility as I'm pretty emotionally compromised right now) and I genuinely don't want to add to her stuff...

Stop making it into a negotiation or messy goodbye. I'd just say something like, "It was really good to see you last week. I've gotten clear that I'm a committed relationship person. I'd be open to having that with you someday. If you ever find yourself free and clear of BF and willing to do this with me, you can let me know. Otherwise, I wish you the best."

Boom! Done. Door left open to a specific condition. Don't respond to anything else. If she reacts with stuff about making her feel guilty, don't take the bait. Just stop responding, and peace out.

[ExpatInItaly]

She is messy. Not much has chamged since her highschool days, it seems. 

She has a boyfriend and is letting another man (you) get way too close. What does that tell you about her character, man? Whatever excuses she comes up with, she is still not single and her interactions with you are not appropriate. She is showing you she is selfish, lacking in ethics and has poor boundaries. 

You are overlooking all of that in favour of...what? Some nice text messages now and then? Itì's time to drop her. She would be a nightmare to actually date anyway, and she's sooner or later going to stop respondng to you. I can nearly guarantee it. You are way over-invested in someone who already has a man and doesn't care much about your feelings. This is going to blow right up in your face all over again. 

Will it have been worth it? 

Edited September 23 by ExpatInItaly

[Repentant]

10 hours ago, Sanch62 said:

Stop making it into a negotiation or messy goodbye. I'd just say something like, "It was really good to see you last week. I've gotten clear that I'm a committed relationship person. I'd be open to having that with you someday. If you ever find yourself free and clear of BF and willing to do this with me, you can let me know. Otherwise, I wish you the best."

Boom! Done. Door left open to a specific condition. Don't respond to anything else. If she reacts with stuff about making her feel guilty, don't take the bait. Just stop responding, and peace out.

Thank you for sticking with this! 

I'm glad to see I wasn't far off, I actually sent her a very similar message several hours before your reply. Also deleted her from everywhere, ensuring that she'll first have to request connections before she can send me anything else.

Sucks, but sucks less than it did two days ago...

[Repentant]

4 hours ago, ExpatInItaly said:

She is messy. Not much has chamged since her highschool days, it seems. 

She has a boyfriend and is letting another man (you) get way too close. What does that tell you about her character, man? Whatever excuses she comes up with, she is still not single and her interactions with you are not appropriate. She is showing you she is selfish, lacking in ethics and has poor boundaries. 

You are overlooking all of that in favour of...what? Some nice text messages now and then? Itì's time to drop her. She would be a nightmare to actually date anyway, and she's sooner or later going to stop respondng to you. I can nearly guarantee it. You are way over-invested in someone who already has a man and doesn't care much about your feelings. This is going to blow right up in your face all over again. 

Will it have been worth it? 

Thank you! 

You are 100% correct, and I'm actually disappointed with myself that I didn't pull a full stop the instant I found out about her relationship status (not to mention how she's handling it...).

Ended it yesterday, left it open for her to reach out if single and interested, but I doubt I'll be hearing from her again.

[Repentant]

Nevermind, she reached out to postpone reaching out (literally just texted me that she's swamped and will get back to me)...

I now officially understand nothing of this situation. Sticking to my guns, though, I can't take this anymore...

[ExpatInItaly]

8 hours ago, Repentant said:

Ended it yesterday, left it open for her to reach out if single and interested, but I doubt I'll be hearing from her again.

May I ask why? 

She has shown you she is of poor character. Do you really thiknk she would ,make a good girlfriend? She isn't even a good friend to you. I personally would not tolerate someone like this in my life. 

You should be asking yourself why you would invite it. 

[Repentant]

14 hours ago, ExpatInItaly said:

May I ask why? 

She has shown you she is of poor character. Do you really thiknk she would ,make a good girlfriend? She isn't even a good friend to you. I personally would not tolerate someone like this in my life. 

You should be asking yourself why you would invite it. 

I'll be honest: right now, two days after cutting it off and receiving the random postponement of communication from her yesterday... I honestly don't think I know anymore...

I'm not thinking of her character right now, but simply how her behaviour is impacting me. Besides the fact that, yes, this is not what one could normally call "friendly" behaviour, I just don't understand any of it anymore. And this ambiguity is compounded by the fact that I'm already walking on eggshells with her after that nasty blow-up, I'm genuinely hesitant to talk about or bring up anything serious with her. And I know that alone prohibits the development of any sort of functional relationship, let alone a romantic one. 

Plus I even told her the only thing I need in any interaction is clear communication, and she responded by ghosting me for two weeks. Again, I'm not calling it abusive given it happened only once so far, but once was enough.

I don't know. My brain's a mess and all I know at this moment is that I need to move on and heal, because I need to not be like this anymore.

Edited September 24 by Repentant

[Sanch62]

8 hours ago, Repentant said:

... all I know at this moment is that I need to move on and heal, because I need to not be like this anymore.

Good. You don't need to figure HER out, that's beyond anyone's pay grade and it doesn't buy you anything.

What I'd take from this is, your younger Self had the clarity to move forward from this person. She may have since tapped some nostalgia in you, but that doesn't count for much when she's a mess and she's trying to take you down that hole with her.

Shoot higher. You will thank yourself.

[ExpatInItaly]

9 hours ago, Repentant said:

I'm not thinking of her character right now, but simply how her behaviour is impacting me

And that is part of your issue, I think. You see these as two separate things, but they are very much intertwined. 

Her behaviour is a reflection of her character. Someone with integrity wouldn't behave the way she does, and thus you wouldn't be so terribly hurt. Now that's not to say this is all on her. You have to take accoutability for your own role in choosing to get inapprorpriately involved with someone who has a boyfriend. Hopefully you will make better choices for yourself in the future. 

9 hours ago, Repentant said:

all I know at this moment is that I need to move on and heal

Good, let this propel you forward. She has once again introduced emotional turmoil into your life. It's time to truly accept that she is not the woman for you, and let of the idea of her for good. 

[Repentant]

2 hours ago, Sanch62 said:

Good. You don't need to figure HER out, that's beyond anyone's pay grade and it doesn't buy you anything.

What I'd take from this is, your younger Self had the clarity to move forward from this person. She may have since tapped some nostalgia in you, but that doesn't count for much when she's a mess and she's trying to take you down that hole with her.

Shoot higher. You will thank yourself.

Thank you! Honestly, I wasn't even looking for a relationship when she reached out, I was on an intentional break from any such things to recharge my batteries. The "what if" was very tantalising, though...

Either way, I'm now setting aside a hefty chunk of time to get good with myself again and to mind my own business. 

[Repentant]

1 hour ago, ExpatInItaly said:

And that is part of your issue, I think. You see these as two separate things, but they are very much intertwined. 

Her behaviour is a reflection of her character. Someone with integrity wouldn't behave the way she does, and thus you wouldn't be so terribly hurt. Now that's not to say this is all on her. You have to take accoutability for your own role in choosing to get inapprorpriately involved with someone who has a boyfriend. Hopefully you will make better choices for yourself in the future. 

Good, let this propel you forward. She has once again introduced emotional turmoil into your life. It's time to truly accept that she is not the woman for you, and let of the idea of her for good. 

I generally don't like to consider that people have a set character, honestly, precisely because I've made my fair share of mistakes over time, and I've learnt to not repeat them since then. I think people have enough capacity for change as to render static characterisations as not all that useful. Instead, I base the way I relate to someone entirely on their behaviour, their words, and resonance/dissonance between the two. I try not to judge people by their worst mistakes, instead to simply learn to work around their behaviours - avoid what is damaging, interact with what is not, adjust and shift as their behaviour does.

In this case in particular, yes. My openness toward something romantic remained applicable for a long time, but my willingness to do so didn't, if that makes sense. As for my share of the responsibility, yes, fully accepted, even course-corrected the instant I snapped out of it and told her outright I'm not comfortable doing anything romantically while she was still in a relationship, I only left it open to friendly chatting. My target for next time is for there to not be a next time. 

And, yes, I agree that, as she has presented herself, an active relationship, either friendly or otherwise, cannot be sustained. I'm not one to hold a grudge, so if she returns later on and presents tangible and consistent change toward something functional (as well as a "thoroughly single" status), then baby steps from friendship and we'll see where it takes us. I do need a bit of time for myself now, just to patch up the bullet holes a bit. But I will most certainly not be pursuing her again, not even just because I can't anymore (deleted any and every way I had of contacting her, just in case the shakes come back...)

 

Edited September 24 by Repentant

[ExpatInItaly]

On 9/24/2025 at 10:11 PM, Repentant said:

generally don't like to consider that people have a set character, honestly, precisely because I've made my fair share of mistakes over time, and I've learnt to not repeat them since then. I think people have enough capacity for change as to render static characterisations as not all that useful. Instead, I base the way I relate to someone entirely on their behaviour, their words, and resonance/dissonance between the two. I try not to judge people by their worst mistakes, instead to simply learn to work around their behaviours - avoid what is damaging, interact with what is not, adjust and shift as their behaviour does.

That's an awful lot of word salad to excuse her current bad behaviour. 

Anyway, you do you. I can't see how any of this serves you, but have at it. Good luck. 

[Repentant]

5 hours ago, ExpatInItaly said:

That's an awful lot of word salad to excuse her current bad behaviour. 

Anyway, you do you. I can't see how any of this serves you, but have at it. Good luck. 

Oh, I'm not excusing anything, which is why I backed off. I just don't use it as a general indicator of who she is. I see no point in labeling.