The answer is both any time and never. Here is the deal, your friend isn’t entitled to his ex, nor is he entitled to you, to dictate what the two of you do, at all. However, they are entitled to have feelings about it and to stop being your friend for any reason or no reason. So it’s less a question of “is it okay” and more “are the consequences or doing this something I can live with.” I generally discourage the idea of dating a friends Ex because the relationship with a friend generally outweighs my desire for romance, especially when there are so many other romantic options on earth, but that I just my priorities, not other people’s and I can’t impress my personal feeling on others actions. That might sound wishy washy, but frankly, there is no right or wrong answer, it’s just a questions of if it is worth it for you specifically.
Now, in the sense of this being a decades old grudge, frankly, that is a long time to hold onto a grudge, and also a long time to hold onto a friend that holds a grudge. I’ve come to think that letting either go is the better corse of action. I had a friend that secretly hated me for years and when I realized, honestly, the best thing was to end contact because the grudge was over things so old literally I wasn’t that person anymore, but they were convinced I was the same old shithead. I expressed regret for the hurt I caused and broke off contact and frankly, I don’t regret having someone that passively seethed against me not around anymore, and I imagine he he happier not having a reminder of the person that slighted him (it was due to taking another persons side in an argument when we were 19.)
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