Dear Maisy:

You are very welcome. I see your guilt feelings being the problem here, guilt feelings that are not based on you doing anything wrong in the context of the friend/ friendly acquaintance (I will refer to her as F, to make it simpler).

In your third post you wrote: “I also don’t like hurting people. Especially when I’m trying to be true to myself. It makes me question my moral compass. I don’t feel we need to accept people back into our lives or to be friends with everyone, but I also don’t feel that I did the right thing or handled it the right way because of the guilt I’m feeling“-

– this quote is telling me (and please correct me if I am wrong) that you are conflicted between being true to yourself and  hurting other people’s feelings, and that the conflict originated when it repeatedly happened in your life (growing up, perhaps) that when you were true to yourself, someone’s feelings got hurt.

Let’s look at what you wrote about F in your original post: “She was always negative and I don’t like to bash people for expressing themselves or getting things out of their system, but it was getting to a point where it affected my mood too after a while. I found myself being less anxious and more at peace when I wasn’t around her. I don’t think she was a bad person by any means, just a bad mood more often times than not. So we both mutually stopped hanging out less and less until we just stopped altogether”-

– seems to me that for a long time, you endured her negativity even though it bothered you a lot; that you did not set limits with her (either limiting the time with her or ending the friendship altogether) because you were afraid that her feelings will be hurt and that she will accuse you of thinking that she is a bad person and of bashing her for expressing herself and getting things out of her system. Too fearful and guilty to end the friendship, it lasted too long: you did not do what you needed to do for your own best interest.

“She didn’t act like she was expecting us to be close again nor mentioned it… she also didn’t seem to care about reaching out or talking more in depth about things“- maybe she was aware of how her negativity affected you in the past (causing the friendship to end), so, she limited what she shared with you, the frequency of contact and she did not reveal her expectations to you.

“I never really considered that she might have had old wounds that she felt were being teared open“- I think that we all have wounds, and seems to me that you have a fear and guilt wound about hurting other people’s feelings when you consider being true to yourself. I think that following her recent critical, angry posts on social media, this wound tore open.

“Should I start to question someone who asks to spend time together what their intentions are?“- depending on the situation and context, it may or may not be appropriate or reasonable to ask for a person’s intentions.

“When you mentioned pay attention to others’ expectations, what is a good approach for this?”- let’s talk about reconnecting with F: “Many years later… she reached out to say hi. It was very casual. She asked if I wanted to come over for a drink one night so I did because why not?“- before agreeing to meet her for a drink, you could have found out somehow (perhaps through her social media postings, or you could have asked her deeper questions) if her life circumstances and negativity changed in those many years of no contact. And based on that information, you could have either not reply to her initial hi, or send her a short reply that would indicate your lack of interest in renewing a friendship with her

“Is it rude at that point to say no, I’m not interested?“- no, it is not rude to be true to yourself and to act according to your best interest. It is not rude to end and not renew a relationship that is not for your benefit.

Overall, I’d say that you really are not responsible for F’s hurt feelings at all, no responsibility whatsoever, and I wish that you didn’t feel any guilt in this regard. If you would like to talk further about F, about your guilt (it would be nice to aim at a Fearless, Guilt-less New Year, wouldn’t it?), etc., please do. I will be glad to read more from you and reply again.

anita