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How do I tell my best mate I'm in love with his sister?

Tagged as: Troubled relationships<< Previous question   Next question >>
Question - (30 May 2011) 4 Answers - (Newest, 30 May 2011)
A male United Kingdom age 30-35, *agn writes:

im with my best mates sister and we have been together for about 3 months but known each other for a few years, my question is that none of her family want us sleeping together but we have and we had great sex but i dont know how to tell her brother (best mate) or her family that we love each other so much and we slept together, what should i do?

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A male reader, Drew21 Canada +, writes (30 May 2011):

Drew21 agony auntI had this exact situation at one point, as well.

My best friend's younger sister was crazy for me, but it just seemed like a highly inappropriate situation because, well, he was my best friend and that was his sister! I tried to fight it, but she was darned persistent and darned cute.

She told her parents, but the both of us were terrified to tell her brother/my friend. One evening we had sneaked out together to go for a walk. I walked her back to the house at 1 am, and we started making out on her front porch and BAM the front door opened. It was her brother letting the cat out. He saw us, didn't say a word, and shut the door.

For the next couple of days he didn't talk to me. Then about 3 nights later he called me and asked if i wanted to hang out. I said sure, and that was that. Not a word was ever spoken between us about the fact that i was dating (and i'm sure they all could figure out, sleeping with) his sister/their daughter.

The fact of the matter is they all knew me, and liked me quite a bit. The biggest concern they would have is that she'll be with someone who will treat her well, and i think they all knew that i was a good guy and that i would.

Let's face it, NO guy wants to think about who is dating their sister, or what's going on behind closed doors, right?

A suggestion for how you can break it to your friend: I would just go and hang out with him one night.. Take him out for a drink, or maybe play some videogames or what have you... Then just tell him straight up. "Dude, I am dating your sister. I hope you're cool with that, cause you're still my best friend."

I would just not tell him (or his parents) that you're having sex. They don't need to hear that.

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A reader, anonymous, writes (30 May 2011):

I had the same situation when i was younger. I started seeing my best mates sister and he wasn't happy about it at all,I think the main reason was he didn't want to see me hurting her and if i did i don't think our friendship would have ever been the same again. It took several months to get him used to the idea and i ended up getting married to her so it all worked out in the end. I think if you are both serious about each other and want to stay seeing each other then your best mate has either got to get used to the idea or tough.

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A female reader, babygirllovej Canada +, writes (30 May 2011):

babygirllovej agony auntHello Vagn,

Your in a very difficult situation. Her family and possibly her brother had already rejected your relationship with her and had clearly objected to you sleeping with her.

No matter how you tell them or what you say; they are not going to be happy.

My advice is to talk with your girlfriend about it. I take it both of you are adults. Talk with the family and explain you are dating. Be causal about it but not insensitive. Don't get upset and keep calm during the entire time. There is no need to tell the family exactly what you two have been up to. No Mother or Father wants to hear that you have been sleeping with their daughter. Keep that to yourselves.

Good Luck.

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A female reader, Aunty Honest United Kingdom +, writes (30 May 2011):

Aunty Honest agony auntWhat's she saying about it? Does she want her family to know because if not, telling them anyway could push them away.

I think you'll have to explain to your best friend that you are in love with his sister, see how he takes that and if you can avoid saying that you've slept together. He might actually be alright with it. I don't think the whole family have to or particularly want to know about your girlfriends sexlife and if they are ok with you being together then surely there needs to be some privacy within the relationship? Wait a while, see what she thinks, and broach the subject gently and carefully. If they don't accept it then there's very little you can do I'm afraid. Just ensure you are respectful of them and her while maintaining yours and her privacy, tricky line to walk but I think you can do it.

Hope that helps

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