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What exactly did I do to screw up and ruin a great friendship I had?

MOPS

Member
Hey All,

I am new to this forum, and I hope this is the right place to post this. So I am a 23-year-old guy that graduated from college a couple years ago, and am slightly on the spectrum. I was diagnosed with very mild asperger's many years ago, and while I function pretty normally to most people on the outside, I still am on the spectrum and struggle with things, specifically what is socially acceptable.

So anyways, during my last year of college, I met a girl that was around 5 years older than me. We'll call her Alyssa. No romantic attraction at all, and she and I have had that conversation before. Anyways, she was one of my resident directors, and was really sweet. As an autistic person, it is hard for me to make friends, and don't have very many. By the way, I was actually a very social and famous person on campus, and had thousands of friendly acquaintances that I'd talk to all the time in passing, but not that many actual friends that I hung out with on purpose or really went past superficial level conversations. Anyways, Alyssa was my resident director and not someone I saw all the time, but I often did see run into her in passing around once a week, and we'd always have great conversations. Alyssa and I really bonded over humor, emotional personalities, and she had such a great understanding of my personality and appeared to really enjoy spending time with me. That being said, Alyssa being a resident director and grad student is a very busy girl and really didn't have a lot of time to give me, but we were able to hangout sometimes. Honestly to me, Alyssa felt like a very close friend because she was someone I could trust and felt comfortable with at first meeting. The main times we spent time together was when I invited her to two very personal parties of mine (birthday party and end of the year party) along with a few other dear friends from college. Outside of that, it was mostly just in passing and deep conversations, although there were a few times where we arranged to meetup for like 30 min just outside to talk a bit. Again, she was an extremely busy girl and really couldn't give me all the time in the world, but the time she did invest in me really meant the world to me, and she still felt like a best friend. We would often message on Facebook quite a bit back and fourth. Alyssa would often tease me and joke with me a lot. I gotta say that Alyssa was kind of like my squish (platonic crush).

After I graduated college, I made it clear to Alyssa that I wanted to stay in touch, and that I really valued her friendship. She reminded me that she is busy and cannot commit to a lot, but would be very happy to keep messaging and stay in touch, and she even asked me to tell her about my life after college, and keep her updated on life things. She gave me a huge long hug goodbye, and then I left.

Over the summer, and throughout the fall of that year, Alyssa and I would message back and fourth, usually about one conversation every two weeks. Sometimes we'd joke, and other times we'd have more serious conversations. It wasn't exactly an equal friendship, and she was kind of more like a big sister / mentor me, and someone I went to for emotional support, but I also did take a huge interest in her life as well (probably too much for how well I knew her). Anyways the relationship was definitely a little unbalanced because like I said, I saw her as like a best friend instantly, while she saw me as more of a very close acquaintance that she enjoys getting to know better. However, I believe it was a common understanding that we saw the relationship a little differently. I often still called her things like: "close friend", "best friend", and "big sister". In all honesty, it might've made her a little uncomfortable, but she never said anything.
 
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Now here is where things start to get rough:

In November, I went back to college just to visit and see some friends. Alyssa, me, and one of Alyssa's best friends (we'll call her Hayley), all got ice cream together and spent a couple hours just talking and catching up. Alyssa told me that she recently started talking to a guy (we'll call him Charlie) and is expects to be dating him pretty soon. I was very excited for her, and started to get really curious about Charlie and her new relationship. I was a little worried as well, and asked the girls: what if Charlie doesn't like me? The girls looked at me and were like: "Why wouldn't he like you? You're such a likable and sweet guy."

A few days later, I left campus and went back home. I was thinking about this new relationship, and was very excited for Alyssa, but was also a little scared, because I was not sure how my relationship with Alyssa would look, whether I will meet Charlie, what Charlie will be like, will he be part of our friendship, etc. I sent Alyssa a message telling her basically that I was very excited for her new relationship but also a little sad because change is hard. I asked her if Charlie knows much about me and if she told him about me.

Alyssa did not respond very well to that message. She texted me back and was like: "It seems you are making my new relationship about you. You are asking what he knows about you, if I talk to him about you. You're telling me your negative feelings about it. If I am being honest, it is concerning that this has affected you like this. We are friends, but our day to day lives do not cross paths much at all. In my opinion this isn't much of a change for you, meaning it's not going to affect your day to day life in anyway, but if it feels that way to you, I am not sure if that is a healthy response. Also I think this is too many questions about Charlie. I'll post about it on social media when the time is right, but otherwise I'd like to remain private about it."

I panicked and apologized to Alyssa and reassured her that I love her new relationship with Charlie and that I support it 100%. She forgave me and told me no hard feelings at all. Things seemed normal but I was still a little concerned about how my friendship with Alyssa will look like and how it will be different now that she has Charlie as her boyfriend. Due to me being concerned, I was looking up Charlie on Facebook and trying to learn more info about him. Due to me being the famous guy on campus, I've never met Charlie, but had a lot of mutual acquaintances that knew Charlie. Throughout the next few months, I was texting and calling a lot of those mutual acquaintances, asking them about Charlie. Some of those mutual acquaintances did not even know Alyssa. Sometimes I included Alyssa in why I was asking, and other times I was just like: "Hey do you know any guy called Charlie? Is he a nice guy? Many people told me that I should befriend him." I was also asking a little more details as to what Charlie's personality is like and if they can see he and I being good friends.

Throughout the time, Alyssa seemed a little more distant and at one point, I didn't hear from her for a month. She got back to me after a while and told me that she had been off social media for a while and just didn't see my messages. She mentioned that she was stepping away from social media more and more, but told me that instagram might be a better way to keep in touch as she's on there more often.

On another note, Charlie and I already happened to be friends on Facebook prior to when I even knew that they were dating due to just my huge network of people from college. I started to be friendly with him because I wanted to get to know him and be friends. On their post about being boyfriend and girlfriend, I did write that I loved both of them so much and that they were my favorite couple in the world. Alyssa later told me that it was very weird because I've never met Charlie and she asked me how I can love Charlie and him be part of my favorite couple if I don't even know him.

It seems that all this asking about Charlie and details started to get back to Alyssa and Charlie, and I think it made them both very uncomfortable. This was probably the last straw for my friendship with Alyssa, but I made an instagram story complaining about close friends of mine not responding to my messages in a timely manner and sometimes taking a few days. I was upset with that. Alyssa saw that story, and felt targeted. She told me that that post really hurt her feelings and it makes her hesitant to have future conversations with me. She told me that I've put very high expectations on her friendship that she cannot meet, and that if she fails to met my expectations, she's worried that I'll get upset and address it publicly.

I told Alyssa that I was really sorry for posting that post, and that I was crying so hard. I was afraid that the friendship might be over, because of how she explained that she was very hesitant to have conversations with me. I told her that I was crying and that I would hate to lose her friendship over that post. I reminded her of how sweet of a friend she has been to me for over a year, and how much she has blessed me, and the emotional attachment I had to her. I also mentioned that I was very upset with myself because I hurt her feelings. Alyssa did not respond to that message. I have a strong feeling that it might've made her uncomfortable. Any idea why?

The next day, following a date that Alyssa and Charlie went on, Charlie hid his instagram stories from me. I wasn't sure why, and really started to panic when I saw that. It made me ask a lot of mutual acquaintances more about Charlie to try and figure out why he did that.

Things were really starting to seem off with my friendship with Alyssa, and later asked her about it. I didn't hear from her for 3 weeks (didn't reach out either). She thought about it for a week and told me that she thinks it is best that we re-evaluate the relationship. She mentioned that I view friendships more intimately than the other person and that causes me to put "best friend" expectations on relationships that should really be "close acquaintance expectations". She said that the recent interactions and the social media post made her uncomfortable and pushed her away. Then she also said that she was told by a number of people that I have been asking around about Charlie and making up scenarios about people saying I should befriend him. It was making both of them feel uncomfortable because I'm asking several people about him before even meeting him. She said that my interest in their relationship is extremely high which she doesn't think is warranted because I don't know them that well. Another thing she mentioned was that I will sometimes send her several messages, unsend them, and resend more messages before she can even read the first ones. I often did this when I felt things were off because I was paranoid about the wording I use might come across, and didn't want to further damage the friendship. Also a few times, I did that because I felt it might get her to look at her messages faster if I just sent an unsent message as a reminder. Alyssa concluded that all that was making her feel very weird, and that it seems I was trying too hard to be very close to her and Charlie and it's just feeling very forced and unnatural. She said that she didn't want to give me false hope that she can be my close friend if she is not going to follow through with it, and that she can't make me a top priority like a very close friend. She said that she wasn't comfortable continuing the relationship as it currently was and would feel more comfortable to remain cordial acquaintances. She said this: "I'd hate to continue not reading and respond to your messages in a timely manner so I think it's best we don't message anymore."
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I was extremely devastated after hearing that, and I couldn't think of what I did wrong that made her so uncomfortable. She obviously said, but I don't get why would just asking about her boyfriend make her uncomfortable? Why would unsent messages make her uncomfortable? I understand why the social media post hurt her feelings but I apologized for that and promised not to do it again. Did it maybe seem obsessive to her? Was telling her that I was crying and that it would hurt so much to lose her friendship over the post, and that she was so important to my life, not a good idea? How would that make her uncomfortable if it did?

I understand that she can't be my close friend, but it doesn't mean I don't value that friendship we had, and still appreciate greatly. It almost feels like a death to me. It seems suddenly she went from being so understanding and loving, to cold and distant now. How come? Did I cross any of her boundaries? If so, what boundaries did I not respect?

Honesty, is what I did creepy? Please explain this to me, because I don't understand. I really do not want to make this mistake again with any other friendship in the future.

P.S. Sorry for the long post.
 
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Hi and welcome. I am worried for you that you cant understand what went wrong here. You've explained that from the start she had concerns about your reaction to her relationship. She was very clear about those concerns, but it seems you completely ignored her feedback and behaved inappropriatelyby checking up on this person and being generally obsessive and inappropriately curious. This got back to her, and that's why she now has distanced herself. I don't think it's hard to understand, you were intrusive and ignored her clear feedback. Another time, listen to the person's clear and explicit concerns and do as they ask, instead of behaving like a stalker.
 
To put it in it's most simplest terms - your anxiety makes other people anxious.

Your actions were based from fear of not knowing this man and it spiralled from there. But you acted upon the fear, and the spiralling and it means your behaviour towards her and her friends was way too intense, and fuelled by fears which probably weren't based in reality.

At the end of the day, she'd started dating someone, you were nervous because you hadn't met him yet. Maybe fear of the unknown?

Eventually you would meet him, but you perhaps were pre-empting things, because not knowing or meeting him was a variable that made you very uncomfortable. Too many "what if's" perhaps? So you set off on a bid to find some form of "known" about Charlie or "expectations" through what others knew of him. Yet I fear you began instigating a plan that was based from a place of fear. Which meant the conclusions to it, are likely going to be off-putting.

Here's the rub - when you act in a clingy manner, it's often in a bid to bring people closer, or to know them, or supposedly care for them better. But people are all individuals - and clinginess often has the opposite effect to what the person had hoped. You want people to be closer, but you push them away. People don't want to feel stifled.

Same goes for sending too many messages, or unsending and deleting them. This gives off an odd vibe, and again - it'll come across as too intense and clingy. You have to respect boundaries, and as Thinx said above - your friend stated her concerns early on, but you circumvented that. Again, I think driven by your anxiety and the escalating thought processes behind your fears and worries.

Feeling a little nervous about meeting someone new is natural, but turning it into obsessive behaviour that makes people nervous isn't healthy for anyone involved.

How could you do things different in the future?

"Expect nothing, and accept everything".

Doesn't mean you have to like or enjoy everything you accept, but if you attempt to let go of your expectations of people, events, situations, past, present future - and try and be more present in the hear and now. Often it's our expectations which bruise our ego. When things don't play out in life how we hope or expect them to.

Ed
 
I honestly do kind of empathize with you here, because I used to be the "clingy friend" with my female friends when I was a freshman in college (a difference here being that I'm also female, and this was a decade ago.) I had never really had friends prior to that (except for in very early childhood) so I didn't know how to behave in an adult friendship.

It did make everyone uncomfortable, and I ended up losing a lot of friends, and getting bullied and having hurtful rumors spread about me because of it, and having a reputation as the "weird autistic girl." I did realize pretty immediately that what I did was wrong though, and I did talk about it a lot in therapy.

I've never talked about this on here, but I very clearly remember an issue from when I was about 19 where my best friend at the time (let's call her "Bridget") started hanging out with this other girl a lot (I'm going to call her "Chelsea") and the three of us would hang out together, and if we were in a nightclub or something Bridget and Chelsea would just go off by themselves and leave me sitting at the bar alone feeling really awkward. I tried to talk to them about it, and they said that I was weird and awkward and they got along better with each other than either of them got along with me. I cried about it for days. I think in retrospect I probably had romantic feelings for Bridget, and that was what made it so hard. But that was kind of the breaking point when I realized I needed to talk about it in therapy.

I'm not clingy with my friends at all anymore; as I've gotten more comfortable with myself I've gotten to be much more independent and have better boundaries, although I do still bond closely with friends (not just women.)
And honestly, sometimes I do still catch myself getting worked up and anxious if a friend doesn't respond to a text message in a timely way, and I think maybe I did something wrong, but the feeling does pass eventually and I don't act on it.

Hope this was helpful. I'm really embarrassed and anxious to share this on here because I don't want to be judged, and I don't open up a lot about personal things or mental health, or sexuality. But I hope this helps the OP and also help people understand where the OP is coming from a little bit. I have been there, and it sucks. But I did grow up a lot. I have been friends with my current (male) best friend since a bit after this dark time in my life lol... so almost 10 years :)

By the way, completely off-topic, but I really wanted to share with you that "Mops" is a nickname that some people gave me in college too... partially because I have a "pug" nose and big eyes (pugs are called mops in most languages), and partially because I have really thick fluffy hair. I doubt that it's your username for the same reason but just thought that was cool, because I have never met anyone else with that nickname.
 
People here have provided you with good insight. You crossed the line when you inappropriately interposed yourself in a private relationship. Regardless if a relationship is friendship or more intimate, your partner deserves and probably expects privacy. Even in marriage there is the expectation of some level of privacy. Your actions in breaching privacy would be seen by many as being controlling, and is a big red flag in any relationship. Most people push back against perceived controlling behavior.

I had a great deal of social anxiety yet still desired friendship and an intimate relationship. That led me to misjudge situations like that which you found yourself. It was a hard balance between wanting to be close and recognizing when another person needed autonomy. That led me to personalize things too much. This was also a time when I did not have strong boundaries. I probably eliminated much of the clingy behaviors once I developed my personal boundaries as I was becoming more sure of myself.
 
Hi and welcome. I am worried for you that you cant understand what went wrong here. You've explained that from the start she had concerns about your reaction to her relationship. She was very clear about those concerns, but it seems you completely ignored her feedback and behaved inappropriatelyby checking up on this person and being generally obsessive and inappropriately curious. This got back to her, and that's why she now has distanced herself. I don't think it's hard to understand, you were intrusive and ignored her clear feedback. Another time, listen to the person's clear and explicit concerns and do as they ask, instead of behaving like a stalker.
I see what you mean, but originally, I did not know exactly what was concerning her when she addressed her concerns. What was she trying to say that concerned her when it said that she was concerned that it affected by me like this? I think because I’m autistic, I missed the point she was trying to make. Why was she concerned?

Was what I was doing kind of stalkerish as well?
 
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To put it in it's most simplest terms - your anxiety makes other people anxious.

Your actions were based from fear of not knowing this man and it spiralled from there. But you acted upon the fear, and the spiralling and it means your behaviour towards her and her friends was way too intense, and fuelled by fears which probably weren't based in reality.

At the end of the day, she'd started dating someone, you were nervous because you hadn't met him yet. Maybe fear of the unknown?

Eventually you would meet him, but you perhaps were pre-empting things, because not knowing or meeting him was a variable that made you very uncomfortable. Too many "what if's" perhaps? So you set off on a bid to find some form of "known" about Charlie or "expectations" through what others knew of him. Yet I fear you began instigating a plan that was based from a place of fear. Which meant the conclusions to it, are likely going to be off-putting.

Here's the rub - when you act in a clingy manner, it's often in a bid to bring people closer, or to know them, or supposedly care for them better. But people are all individuals - and clinginess often has the opposite effect to what the person had hoped. You want people to be closer, but you push them away. People don't want to feel stifled.

Same goes for sending too many messages, or unsending and deleting them. This gives off an odd vibe, and again - it'll come across as too intense and clingy. You have to respect boundaries, and as Thinx said above - your friend stated her concerns early on, but you circumvented that. Again, I think driven by your anxiety and the escalating thought processes behind your fears and worries.

Feeling a little nervous about meeting someone new is natural, but turning it into obsessive behaviour that makes people nervous isn't healthy for anyone involved.

How could you do things different in the future?

"Expect nothing, and accept everything".

Doesn't mean you have to like or enjoy everything you accept, but if you attempt to let go of your expectations of people, events, situations, past, present future - and try and be more present in the hear and now. Often it's our expectations which bruise our ego. When things don't play out in life how we hope or expect them to.

Ed
BINGO! I couldn’t have said it any better myself. It’s exactly how I felt. I was basically instigating a plan in my head due to fear, but why was that so off putting and uncomfortable for them?
 
I honestly do kind of empathize with you here, because I used to be the "clingy friend" with my female friends when I was a freshman in college (a difference here being that I'm also female, and this was a decade ago.) I had never really had friends prior to that (except for in very early childhood) so I didn't know how to behave in an adult friendship.

It did make everyone uncomfortable, and I ended up losing a lot of friends, and getting bullied and having hurtful rumors spread about me because of it, and having a reputation as the "weird autistic girl." I did realize pretty immediately that what I did was wrong though, and I did talk about it a lot in therapy.

I've never talked about this on here, but I very clearly remember an issue from when I was about 19 where my best friend at the time (let's call her "Bridget") started hanging out with this other girl a lot (I'm going to call her "Chelsea") and the three of us would hang out together, and if we were in a nightclub or something Bridget and Chelsea would just go off by themselves and leave me sitting at the bar alone feeling really awkward. I tried to talk to them about it, and they said that I was weird and awkward and they got along better with each other than either of them got along with me. I cried about it for days. I think in retrospect I probably had romantic feelings for Bridget, and that was what made it so hard. But that was kind of the breaking point when I realized I needed to talk about it in therapy.

I'm not clingy with my friends at all anymore; as I've gotten more comfortable with myself I've gotten to be much more independent and have better boundaries, although I do still bond closely with friends (not just women.)
And honestly, sometimes I do still catch myself getting worked up and anxious if a friend doesn't respond to a text message in a timely way, and I think maybe I did something wrong, but the feeling does pass eventually and I don't act on it.

Hope this was helpful. I'm really embarrassed and anxious to share this on here because I don't want to be judged, and I don't open up a lot about personal things or mental health, or sexuality. But I hope this helps the OP and also help people understand where the OP is coming from a little bit. I have been there, and it sucks. But I did grow up a lot. I have been friends with my current (male) best friend since a bit after this dark time in my life lol... so almost 10 years :)

By the way, completely off-topic, but I really wanted to share with you that "Mops" is a nickname that some people gave me in college too... partially because I have a "pug" nose and big eyes (pugs are called mops in most languages), and partially because I have really thick fluffy hair. I doubt that it's your username for the same reason but just thought that was cool, because I have never met anyone else with that nickname.
Thanks, and LOL about MOPS. Nah, it's my username because it stands for an organization called: Mothers of Preschoolers.
 
BINGO! I couldn’t have said it any better myself. It’s exactly how I felt. I was basically instigating a plan in my head due to fear, but why was that so off putting and uncomfortable for them?

Because it crossed a boundary from normal behaviour, into anxious, fretting and clingy behaviour. Your anxiety will make others anxious. That in turn will push people away.

Ed
 
Because it crossed a boundary from normal behaviour, into anxious, fretting and clingy behaviour. Your anxiety will make others anxious. That in turn will push people away.

Ed
That makes sense. I think it was coming to the point where they felt that I had so high expectations that were obsessive, and they felt uneasy because they were worried about what I would do if they didn’t meet my expectations. They probably didn’t feel safe.
 
Just because we really like a friendship doesn't give us the right to be clingy or know what they are doing or who they see.
 
Welcome, and sorry about the situation.

I too sympathize as I've similarly lost a connection with someone in a similar dynamic as yours - where they were a valued mentor to me, but I was more of a acquaintance to them - and looking back, while I wanted to turn it into a friendship, I missed reading the signs that they had no interest in that (e.g. responding to messages with thoughtful responses and advice while ignoring requests to meet up / hang out).

For those of us without many friends, an good acquaintanceship could mean the world, but we have to be careful to understand that at the end of the day, we are an acquaintance, and that if they're busy for whatever reason, that we may end up dropping out of their life. And that happens even with friends. It's scary to potentially lose something valuable to you through no fault of your own, but that is life.

But at the same time, when one door closes, another may open.

Don't let the loss of one acquaintance stop you from building connections with others, especially if they're initiating things and offering their friendship. I was so upset about losing that mentor that I was scared of losing other acquaintances, including ones I've made later, and so I would turn down offers to meet up and other expressions of interest in friendship. I guess I'm sharing this in hopes that unlike me, that you can learn and not, out of fear, withdraw and miss out on opportunities elsewhere.

One advantage that you'll have, which wasn't as prevalent in my days, is lots of places on the internet, like this site, where if needed, you can ask for help in interpreting a situation.

You're still quite young and have lots ahead of you. I hope that as the saying goes, whatever doesn't kill you makes you stronger.
 
Welcome, and sorry about the situation.

I too sympathize as I've similarly lost a connection with someone in a similar dynamic as yours - where they were a valued mentor to me, but I was more of a acquaintance to them - and looking back, while I wanted to turn it into a friendship, I missed reading the signs that they had no interest in that (e.g. responding to messages with thoughtful responses and advice while ignoring requests to meet up / hang out).

For those of us without many friends, an good acquaintanceship could mean the world, but we have to be careful to understand that at the end of the day, we are an acquaintance, and that if they're busy for whatever reason, that we may end up dropping out of their life. And that happens even with friends. It's scary to potentially lose something valuable to you through no fault of your own, but that is life.

But at the same time, when one door closes, another may open.

Don't let the loss of one acquaintance stop you from building connections with others, especially if they're initiating things and offering their friendship. I was so upset about losing that mentor that I was scared of losing other acquaintances, including ones I've made later, and so I would turn down offers to meet up and other expressions of interest in friendship. I guess I'm sharing this in hopes that unlike me, that you can learn and not, out of fear, withdraw and miss out on opportunities elsewhere.

One advantage that you'll have, which wasn't as prevalent in my days, is lots of places on the internet, like this site, where if needed, you can ask for help in interpreting a situation.

You're still quite young and have lots ahead of you. I hope that as the saying goes, whatever doesn't kill you makes you stronger.
If that is the case, I think it’s not really a comparable situation. I’d like to ask you, what did they mentor you in? Was that mentorship agreed upon before hand? What was your relationship with this person in the first place? How did you get acquainted? Were you the same gender?

I left this out of my post because I didn’t think it was relevant, but Alyssa did not appreciate that she felt like a mentor to me, and while she admired my desire to grow and loved giving me wisdom, she really desired the relationship to be more of friendship but we just were not there yet and she only saw me as an acquaintance because we didn't hangout that much. Alyssa never turned down an opportunity to hangout.

The main reason why Alyssa ended the relationship was because of what I was doing that made her uncomfortable, not because she wanted me out of her life in the first place. She lost trust for me. If she was just busy, she just wouldn't be able to give me the same kind of time, and that's ok, but it doesn't mean I'm out of her life, it just means I ain't a priority which I never was in the first place for her and that's ok. I am very intentional with relationships in general and even if I only get to see them and get a meal with them like 2-3 times a year, that still means the world to me. I would never think it isn't worth it. I maintain a lot a lot of distant friendships that are more like close acquaintances. I don't talk to them super often, but I always make it a point to see them at least once a year (many are long distance), and it still is very valuable. Just because I am not their priority doesn't mean they are not worth investing in.

I don't think like others. I personally do not need my efforts and feelings reciprocated in the same way with friendships. I am content as long as they are just intentional in texting whenever available and getting a meal from time to time even if only a couple times a year. They could still feel like a very close friend to me if I trust them and feel comfortable around them.

Most NTs would probably drop relationships like that, and wouldn't invest at all, but I see things differently.
 
Life happens and this can change things. I have gone through two hurricanes, the pandemic, working 6 days a week -8 to 9 hours, to many stressful moves, if people are still friends with me after all that, it's pretty amazing. Think we need to step back and just acknowledge life happens, it does affect our friendships.

Sometimes friends can't reciprocate the way we wish they could, but they have zero obligations to us, just as we have zero obligations to them. It could be our definition of friendship is maybe unrealistic.
 
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If that is the case, I think it’s not really a comparable situation. I’d like to ask you, what did they mentor you in? Was that mentorship agreed upon before hand? What was your relationship with this person in the first place? How did you get acquainted? Were you the same gender?

It pains me to say this, but your questions, in my opinion, cross the line into being socially inappropriate.

There's a natural give and take in conversations, and where one may invite someone to elaborate on something, or to ask for an opinion or comment on something, but the questions you're asking are rather pointed, and in succession, and made/make me feel uncomfortable, as it seems that rather than a casual conversation, that I'm being interrogated.

I understand that details and facts are important to you and help you understand and interpret things, but when it comes to people, one should be letting the other party talk as they wish, rather than "putting them on the spot" unless they had explicitly stated that they were okay with answering specifics.

If this was the way you were asking about Charles, I can see why it got back to him and Alyssa very fast - because this style of fact finding is one that people will get upset by and talk to others about.
 
It pains me to say this, but your questions, in my opinion, cross the line into being socially inappropriate.

There's a natural give and take in conversations, and where one may invite someone to elaborate on something, or to ask for an opinion or comment on something, but the questions you're asking are rather pointed, and in succession, and made/make me feel uncomfortable, as it seems that rather than a casual conversation, that I'm being interrogated.

I understand that details and facts are important to you and help you understand and interpret things, but when it comes to people, one should be letting the other party talk as they wish, rather than "putting them on the spot" unless they had explicitly stated that they were okay with answering specifics.

If this was the way you were asking about Charles, I can see why it got back to him and Alyssa very fast - because this style of fact finding is one that people will get upset by and talk to others about.

That makes sense. I was definitely asking about Charlie in this way. I was intentionally calling and texting mutual friends for the sake of trying to fish for information about Charlie, his personality, and what he is like. It didn't just come up in a conversation, I intentionally asked a few people to talk to try and get information about him specifically. I was trying to get details and facts about his personality and the kind of person he is.

I was basically trying to investigate Charlie as a person and their relationship.
 
I think you already know the answer to your question, but I'm not sure. IMO all the responders are providing good, accurate assessments, but it's being sugar-coated a bit.

If you'd like a short, direct response, without the sugar-coating say so.

A useful principle, which you might think about either way:
"The level of relationship between two people is set by the least interested party"
 
To add, some people you are friends with, when they find a partner, they don't necessarily want to keep all the friends they have. It might be too much for them to deal with, they might be being too selfish, etc. When someone commits to someone else, they only have so much energy in a day. So, maybe they need to take several days to respond. Your former friend was willing to be appropriate direct and honest with you. Sounds like it was at least a semi-quality friendship. It's hard for me to tell if waiting a few days for a response is reasonable or not. If you're good friends arguably, it seems there would be an understanding that she's taking so long to respond sometimes not because she doesn't care about you, but because she is overwhelmed.

I can understand your struggle too, but how you definitely did take it too far too.
Sometimes, if I'm not sure if something is working out or not, a good barometer for a test is ask about hanging out and plan in advance. Ask to meet in-person. If this is not or no longer feasible, maybe this is not a friend worth keeping then and it's best to move on./

I think you are like me in the sense that we both probably don't like endless chatting.
If a person is not willing to plan with you to hang out in advance, even if it's months in advance, a good way to create your own social boundaries and move on is to say something like "please contact me when you know a date and time we can meet in-person. I am not looking to chat endlessly." Of course, don't start off with that kind of statement, but this is a good way to end things off if things just aren't working out. That way, you can focus on building new friendships that will hopefully last.

I'm finally realizing that people don't always deal with change well, or they do but changes change people in ways that maybe they change what or who they are interested in. It's not always supposed to make sense. I wish you much luck for your future social life. It's not easy, even if people make it look like it is.
 

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