Anxiety Aunt: Help! My sister doesn’t want me dating someone she once dated but I think he could be the one

Dear Aunty, I am writing to you in a bit of a dilemma. My sister and I are very close and usually I would choose loyalty to family over everything, but a few months ago she started dating a guy who is in our extended friendship circle. They went on two dates and decided they were better off as friends. A month or two later, we were out in a large group which included him. My sister wasn’t feeling well so left early and I stayed out. I ended up sitting next to the guy at dinner and we got chatting for the first time in a while. We got along so well and I ended up having such a fantastic night. The next day he messaged me to say that he had too and would I consider seeing him again. I decided meeting up once wouldn’t hurt so we went for brunch, which turned into a late lunch, which turned into a late dinner. It was such an amazing day. I ended up telling my sister and she was really angry, which I found confusing; after all, it was never serious between him and her and she said she didn’t have feelings for him. He has been asking to see me again but I am really conflicted. I have never got along so well with a guy and think he could potentially be the one for me, but I am worried about losing my sister over it. What should I do? Yours, Torn Dear Torn, Loyalty is a wonderful character trait. But it should also be a two-way street. If your sister simply went on a couple of casual dates with this fellow then they mutually decided not to pursue anything further, then it is not really as if you are trying to cut her grass. If they had dated for a while or she still harboured feelings for him then I would say you should give serious thought as to whether it is worth jeopardising your relationship with your sister over. However, given she seems uninterested, her anger seems unjustified. That is, unless she is lying to either you or herself about her true feelings, in which case her annoyance makes more sense. Or perhaps this situation has stirred up some long-repressed memories of a similar situation in the past where her feelings actually did get hurt? Your Aunt could just be clutching at straws there, Torn, but it is worth examining all the options to work out why she is feeling the way she is. In your Aunt’s time as a globetrotting internationally acclaimed cancan dancer, boyfriends were practically interchangeable. Sometimes feelings got hurt along the way and often fur (or, rather, patches of hair) would fly in jealous rages, particularly if the timelines of one relationship starting and another ending seemed somewhat blurred. But blood is thicker than water and losing a friend (I use that term loosely because dancing is a cutthroat industry and it is generally a case of every dancer for themselves) didn’t seem like a big deal, whereas losing a sister could be something that impacts you for the rest of your life. So how to proceed, Torn? Well, first One would put the potential paramour on ice. If he is as keen as he seems to be, then he will wait. One would do some soul searching to try to get to the bottom of your sister’s behaviour, then One would suggest you talk things through with her. Let her know that you are developing serious feelings for this man and that you think it has real potential to be a long-term proposition and not just a short-lived fling. Ideally you really want her blessing because starting on the wrong foot is no way to be in a new relationship. If she does not or will not give that to you, then you will have to decide if you risk going ahead with the relationship and perhaps losing her in the process. It’s a very high price to pay and one that many who have paid it have lived to regret.