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Should I date my best friend's ex?

Eda M. Handly • Mar 27, 2013 at 3:00 PM

Q: My best friend had been friends with a guy for a year. Well one summer, this guy and I had ended up at the same summer camp by chance and I really started to like him. We texted all the time after we left and my best friend knew, actually she gave him my number. We sort of fizzled out because I was kind of scared to dive into a relationship. But I still pined over him. Three months later he asked out my best friend. They've been going out since last September, up until a week ago. I still texted him throughout this time but more casually, though we still had the same chemistry. When they broke up, which was a mutual decision because they basically got bored with each other, I started talking to him again without mentioning the breakup and we hit it off again. I know he's my best friend’s ex but I have liked him for so long before they dated and I am just not over him. And when I finally started to think I was over him, they broke up. I know I'm thinking with my heart. It's so hard not to do. Is it OK to start dating him again?

A: This question is not easily answered. I remember an unwritten rule about steering clear of any guy a good friend dated. However, it can also depend greatly on the circumstances. You did date him first but was it serious between he and your friend? Have you even talked with your friend about it? Did she give you the go ahead? I understand how you could possibly still have feelings for him, but remember you originally broke it off with him because you didn’t want a “relationship.” So, what changed your mind? There are certainly more guys out there to choose from. If you’re set on dating this guy, the person you should be asking these questions to is your friend.

Q: My situation is very complicated. I’m in love with this girl who is thousands of miles away studying overseas. The problem is I've known her for more than five years, but I fell in love with her three years ago. We've been good friends and texting almost daily. She is also my best friend's sister. I think she is really into me, but I couldn't tell her that I love her because her brother is my best friend, and I didn't want to lose either of them. She told me two weeks ago that she doesn’t want to have a relationship right now. These past couple months we didn't text much due to an eight hour time difference. I always text her first so I really think she doesn't have any feelings toward me. I always considered telling her how I feel and I want to have a relationship with her, but what if she rejects me or maybe I lose my best friend? If she does say, yes, I love you, what about the distance between us? How it is going to work? I'm really confused. What should I do? Should I tell her or move on? In the last year it was hard for me to sleep because all of the thinking and what would happen if I tell her. I really don't want to lose her. I want to tell her that I love her but not in a direct way. What should I do?

A: You can’t lose something that you don’t have. Regardless of whether you had feelings for her before she left, it’s near impossible to have any type of relationship with someone who is thousands of miles away. Not to mention, I don’t think your best friend would appreciate the idea of you obsessing over his sister. This is yet another unwritten rule or secret code of ethics, if you will. It’s fine to be friends, care about her, and even keep in touch, but you are venturing into unchartered waters that will surely leave you drifting alone in a tattered raft in the end.

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