• Handling Breakups

Hard To Say Goodbye: Ending A 20-Year Friendship

Published: December 12, 2009 | Last Updated: January 14, 2024 By | 12 Replies Continue Reading
Even if the relationship hasn’t been perfect, it’s hard to say goodbye to a 20-year friendship.



I have spent countless hours trying to understand what happened to my friendship. I’m 63 and Donna is 67.

We met at work and shared the same office for about ten years. Donna talks about herself and her problems constantly. Whenever anyone would come into the office, she would monopolize the conversation. Over the years she has told me every personal detail about her kids’ drug problems, her kids’ marriage problems, that her son that wanted to give up his parental rights to his ex-wife, about her mother’s problems, and about her husband’s medical problems (he’s been quite ill for the past year). I could write a book.

Before I retired more than ten years ago, my husband and I purchased a 100-acre parcel bordering her and her husband’s property. We built a house, business and barns. Donna and her husband are equestrians but only have 2 acres for their horses. After listening to her talk about her horses, riding, and horse camping for many years, I purchased a horse.

For the past 12 years, Donna, her husband, and I have been trail riding on our property together at least twice a week. Donna and I also belong to ladies’ riding group and ride together at least 4-5 hours every Tuesday.

In June, James and Donna went to visit their son in Lexington. When they returned, they talked about how their son and daughter-in-law couldn’t wait for them to leave after the visit. I said, “It would be better if you lived closer and you wouldn’t have such long visits.” They insisted they weren’t ready.

During the summer, we continued to ride and they never talked about moving. She did drop comments like, “I won’t be planting my greenhouse next year” and “James won’t be getting wood” and “We won’t be able to keep the horses.” I assumed James was very ill or maybe she was. Although I was worried about them, I didn’t want to ask.

Just before they went back for another trip, Donna called and said they had been looking for property, had found a lot on the internet, and would be moving so James could be near their son. I said, “I understand, but I will sure miss you.” They left to purchase the property and I went on a weeklong camping trip with several of the gals that ride together.

Our rides with Donna and her husband generally lasted about two hours with her talking all the time. James and I can’t get a word in edgewise. The rides are always at 1:00 or 1:30PM. If I say I would like to go at 2:30, she says, “No, we need to go earlier.” It’s her way or the highway.

When she called to ride after they returned, she started talking about the nice property they bought, a neighbor she couldn’t wait to meet, etc. She went on to say how it was up to her to make sure that all the paperwork was in order. She said they were waiting for a call from the title company and would be going back to Lexington to sign papers. She said, “I caught a huge error when we purchased the lot in June and it fell through.”

Then I realized she had purchased property in June and hadn’t told me until now. I asked why. She said in a very controlling rude voice, “That is my personal business I thought you would be upset”. I literally gasped. I said, “I’ll see you on the ride” and hung up but didn’t go that day and I haven’t been on a ride with them since then. I was almost hysterical. My husband said to forget it, but he is a man and doesn’t understand.

She hasn’t called and I haven’t either. I see her every Tuesday to ride with the girls. The first time I saw her after the phone call, she came over to my trailer to give me an apple for my horse. I could tell by her face she was embarrassed and didn’t know what to say. I thanked her and that was it. I didn’t talk to her on the ride. I just can’t get past her hiding the fact all summer that they were moving.

The worst part of this is I do miss her. Twenty years of friendship is a long time. Also, it is very uncomfortable on Tuesdays with the other gals. They know we aren’t talking to each other. I am not friendless. For the past 8 years, I’ve been riding and camping with another couple and another lady. We go on week camp trips as a foursome. I have other close friends: my bridge partner, my walking partner, etc.)

I expect an apology for her rudeness, but that hasn’t been forthcoming and I don’t think it will be. I feel betrayed. What is your evaluation of this entire scenario of the end of a friendship?

Thank you,



You sound pretty ambivalent about your friendship. You enjoyed working, riding, and being with Donna enough to sustain a twenty-year friendship but you also are saying now that you could barely tolerate her incessant chatter, rigidity, self-centeredness, and controlling nature.

It is strange that Donna felt comfortable enough to share so many intimate details of her family’s life with you but decided that telling you about her impending decision to move was too “personal.” I’m also confused why you never asked your friend to explain the comments she made during the summer suggesting that there were going to be major changes taking place in her life. How could you just ignore her comments?

I think you are both having a difficult time ending a long-term friendship that you both enjoyed. My guess is that Donna is upset about her husband’s illness and their need to move, about all the changes that are taking place in her life, about her inability to control everything going on around her, and about moving away from you.

I think you are feeling a tremendous sense of loss as well that feels like a betrayal. To justify your feelings, you are remembering more negative than positive things about her. You would not have kept the friendship going for so long if it wasn’t worth its weight in gold. You have other friends but this was a special friendship that was life changing in terms of all you shared together and because it introduced you to the equestrian world that you now enjoy so much.

Don’t stand on ceremony waiting for an apology. Allow your friend to have made a mistake in not being explicit. She’s leaving and your relationship will be changing as a result. Instead of ending it on an ill note, tell her that you really will miss her and that you hope you can still stay in touch. Not only will this type of reconciliation allow you to feel more comfortable with your friends who are remaining, it will allow you to feel more comfortable about yourself.

I hope this is helpful.


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Category: HANDLING BREAKUPS, How to get over a breakup

Comments (12)

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  1. KH says:

    I feel like I am now ending a 15+ year friendship. It’s a very strange feeling. Myself and the other individual had prior issues in the beginning of the friendship because she “assumed” some things that were not true and for years I felt like I had to walk on eggshells around her because she has such a big personality & we have several of the same friends. So because of this “assumption” I always felt like she “had something” on me , so I never wanted to make her mad or cause any friction and I always agreed with everything she said or did even when she was mean to other people.

    I ended up with Cancer & she and another close friend were right by my side. They were literally my strength. She often would tell me that I taught and showed her what real friendship was because I never gave up on ours(I ended up at one point confronting her about some things). Well, as time went on …I finished up with my treatment, she was newly married after a very difficult divorce and she even started a business.

    Now there were always 3 of us together all of the time, we were like sister…shared birthday traditions together, families, church, our homes…EVERYTHING!

    Well I’ve noticed as time has went on , I am now the odd man out. Our friendship of 3 has now went to a friendship of 2. I was really confused and hurt by this, because I never could get an answer to why. I even sat down and spoke with her about the situation & that I missed her and she stated that she missed me too. That went well for about a month, but now I’m left out again.

    My conclusion is this: I love her like family, BUT I will not chase or hound someone to be in my life. I thought almost 20 years of friendship meant something but I will take what I learned from this friendship and be thankful for those lessons and move on. I’m actually excited about starting new friendships!

  2. LaTrice says:

    I had to end my twenty years of friendship with my ex-best friend last month, and honestly, it wasn’t an easy decision to make. I’ve known him since we were in the third grade, and we do share a history together. Not only was my ex-best friend my confidante, he was the kind of person that was easy to talk to, and would give me the best advice. I will continue to cherish my friendship with him, but it will NEVER be the same again.

    This incident started on Facebook in November of last year. My ex-best friend’s “girlfriend” was talking to trash to me, and I wasn’t going to allow this woman to talk to me crazy, so I put her in her place. Then, my ex-best friend had the audacity to accuse me of disrespecting her, despite the fact that she started some drama first, and I finished it. It seems that she had a HUGE problem of me maintaining a friendship with her man, even though I had known him a lot longer than she has. If she had a problem with me, she could have been woman enough to tell me that in my FACE!! Besides, it wasn’t my fault that she was insecure!!

    The same incident happened AGAIN, but it was ten times worse! My ex-best friend was calling every name in the book, and had the NERVE to belittle me, by telling me that I’m less than independent because my sister takes care of me. Also, he accused me of putting him down, which to me, is so NOT true! I felt that he was nit picking at my actions, when I didn’t do anything wrong. Since he was too busy playing the role of a victim, his actions encouraged me to end my friendship permanently. Why would I want to maintain a friendship with someone that doesn’t respect me as a friend?! I was more of a best friend to him, than he was a best friend to me. He took our friendship for granted, so how much more disrespect can I take!!

    My ex-best friend doesn’t understand the true meaning of friendship, and how important it is to maintain it. He was too busy taking sides, and didn’t bother trying to solve the situation between everyone. It’s obvious that my ex-best friend doesn’t know how to be a friend, and is unable to communicate nicely.

    Maybe one day, I can forgive him for all of the pain and HELL that he has put me through, but unfortunately, I can’t do that right now. I’m not expecting an apology, and I’m going to have to live my life without him in it. Someday, my ex-best friend will have to come to terms with his actions, and hopefully, he will understand that he had lost a good friend.

  3. Lauren says:

    I am sorry that this happened to you. It sounds very painful, but your friend seems like she was already distancing herself from you in her mind, by not telling you, on a timely basis, the very important news of her impending move. Also, she seems to have been a source of annoyance to you at times, even though she was a long-term friend.

    Maybe that’s why they are called “friendships” a friend and a ship…they drift into your life, and they sail out of your life on the same ship. Love yourself and your other friends and family. You deserve to be treated well and with respect. Don’t wait for an apology…maybe she meant what she did and said. Perhaps you could “demote” her to a second tier, or ever a third tier friendhship level, and don’t ever expect too much from her. Anyway, it may be time to move on and remember the good days of the friendship. All the best to you.

    • Friendship Doc says:

      Hi Lauren,

      Maybe that’s why they are called “friendships” a friend and a ship…they drift into your life, and they sail out of your life on the same ship.

      I love this metaphor and never quite heard it expressed this way!

      Best, Irene

      • Lauren says:

        Hi Irene,

        I just wanted to say thanks for your thoughtful and kind response to my comments of Feb 04 2013. I am sorry that this reply isn’t very timely, but I guess, better late than never. I love your website, and all of your great advice. You are indeed a bright, insightful, highly intelligent , analytical and compassionate wise woman. All the best to you. Lauren

  4. Irene says:

    Thanks so much for letting us know the outcome. We rarely have that opportunity. It sounds like you’ve gotten past this loss.

    I might mention…you deserve a longevity award for sticking around here, too! I appreciate your contributing your experience then and now.

    Warm regards for the New Year!

    Best, Irene 

  5. Anonymous says:

    Since I read this blog frequently, I noticed my 2 year old post was front and center again. Someone asked to me give an update. Unfortunately, our friendship ended and that is very sad. I still remember the good times we had and don’t dwell on the downside. It’s been 2 years, my friend moved and we never did resolve what caused the breakup. One of the gals in the riding group said she didn’t think my friend could apologize. I think is true and now my only regret is that I didn’t take Irene’s advice. I have read advice from other professionals and they say that in every friendship (long term) there is a time when a person will have to bite the bullet and forgive their friend even if they strongly think they have been mortally offended. Hindsight. Irene gives good advice, but it is too late for us as too much time has passed.

    I haven’t developed another BFF within the riding group and don’t want to at this time. We are all friends and rely on each other for support, but there isn’t really any BFF’s in the group. I have other BFF’s so this is fine. I still enjoy everyone in the group and the feeling is mutual.

  6. Anonymous says:

    I realized now this was an old post, so if you get on this board again, please update us.

  7. Anonymous says:

    I think she was rude and there is a difference between true friends and frenemies. Sometimes I believe we had different levels of friendships, and while we can enjoy different aspects of a person , if there are things that you can’t stand about the person also, then they are not a true friend. Rudeness should not be tolerated. She probably is writing you off because she is having a new start. I wouldn’t be surprised though at some point that she does try to contact you in the future.

  8. Anonymous says:

    I understand exactly what you mean about “the tone your friend used with you” because that is exactly what happened to my 20 year friendship. It is hurtful and I agree with you, friends should not talk in that tone with you.

  9. Anonymous says:

    my comment is you have to understand that we are angles, people make mistakes, friends make mistakes, if we are angles then making mistakes should not be forgivable, but we are humans and human can make faults , if you are strong enough do not waste the good moments that you had spent together and try to approach her.

  10. Anonymous says:

    Irene, Thank you for your insight regarding my friendship loss. Reading your comments helped me to see part of what happened. To answer your question as to why I didn’t ask her why she was making comments about not planting her green house, etc. I thought it was because John was ill and they are getting older. I thought she was downscaling and I said this to her when she would comment. “Yes, we all need to downscale when we get older.” She didn’t say a thing about buying property and moving, although, all of the comments “were about moving”. They were made to me in front of her husband while we were riding. They both knew what the comments were about, I didn’t. This really made me sick when I found out. Physically ill that they were commenting in front of me about moving to see what I would say in response, but never telling me.

    Also, the we had the “final conversation”, she slipped when she said they had bought property in June and the sale fell through due to her diligenece in finding a zoning error. She was upset that the realtor was trying to take advantage of her and this wasn’t going to happen this time. That is when I asked, “You mean you purchased property in June to move and haven’t told me during these past 3 months?” Her answer was in a very controlling RUDE tone, “That’s my personal business and I keep my personal business to myself.” I couldn’t believe my ears that she considered moving personal after all of the family issues she had shared with me. The worst part was the TONE OF HER STATEMENT. That was when the memories of her little tidbits of moving information that I thought was about getting older and an illness came rushing in. I felt she was closing a door to our friendship. She has always she is in charge of her husband and sons. I would always go along with whatever she suggested eg. times to ride, days to ride, etc. Even if I would say I needed to go later or at another time, she would NOT budge. I know now that a great part of our relationship was control. Control of me. I will NOT be her doormat anymore. These small things weren’t an issue at the time as it wasn’t a big deal and I could adjust my schedule. Now I see that it was a mistake. Our friendship was based on Control. I just don’t want to Go There again. Things will never be the same. I will never be controlled again. And, I won’t be talked to in that tone by someone who is supposed to be a friend no matter how long our relationship existed. Friends don’t speak to friends in that rude tone, unless, they are writing the friend off. I’m done.

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