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How do I tell my friend that I like his sister? Watch

    • Thread Starter

    My friend's sister, who's a year below me, I've had quite a big crush on since Year 10. I spoke to her on Facebook a few times around that time but never really much in person and I also didn't get to interact with her much either in that regard.

    I thought she showed a few signs at the time of possibly liking me back, but I was always too shy to do something. As time went on, we drifted apart and I thought she didn't see me like that, but when we were both in sixth form a few things started to happen which once again possibly indicated to me that she may still like me.

    I'm at uni now and she's in Year 13 at my old school. I recently posted a question online where I explained this situation in much more detail and from the answers I got, the general vibe was "it sounds like she liked you at the time but may have moved on now" but one also mentioning how her acting around me later on could have indicated her wanting to see possibly what I thought of her now.

    The point is, she's one person in particular who I've kept thinking about from time to time over others and although I've left it so long, I really would like to try and see if maybe we could still get something to work, assuming she likes me as well? I wonder maybe if she did like me back then, she may still give me a chance now?

    One thing though is that I have yet to tell my friend about any of this. I still talk to and see him from time to time so we're still good friends. He once joked that it would be "so cool" if I did get with his sister because he could effectively be my brother-in-law so I do think he'd be OK with it, even if this was a few years ago now.

    In less than a month's time I'll be home for Summer so if anything were to happen, this would be a good time to act on it. I think that finally telling him how I feel about her would be a good first step towards this, despite how late I've left it, only I don't know what I'd say or how I'd phrase it? I really don't want this to ruin our friendship.

    Of course she herself will most likely be going to uni in September, which could present its challenges if she went to one really far away from mine, but if she went to one quite nearby then it would be much easier. Either way though, I'd be prepared to travel if we were serious by then.

    Thanks for any suggestions!

    tell your mate whats going on. If he is your actual friend he will stick by you. If he is not then it goes to show you that he was never there fore you. GOOD LUCK MATE

    Well, I'd suggest taking it slow....even though you already have. Do you know she's not seeing someone? If she's not once you're back in town maybe just send her a fb message saying you talked to your friend (her brother) and he said she was graduating and congratulate her (something casual like that that wouldn't seem too weird for you to be randomly contacting her). Then hopefully you'll have a conversation that way. Then casually ask if she'd like to grab a coffee. Ideally, she'll say yes and you can meet for a casual coffee and see how the conversation and overall experience feels. I think you might risk it getting too formal if you tell her brother first then ask her out on a date... it might just feel too stiff and officially instead of just seeing how you organically get along. Also, then you're going to have to 'report' on how it went if you tell him first. I suggest you take her for coffee and see how it goes.... if it goes well then ask her out on an official date and tell her brother and explain that you didn't want things to be awkward if you told him first that you were asking her out (for the coffee0 but it didn't go well.

    It sounds like her brother would be happy for you to go out with his sister so it doesn't matter if you talk to him first or not really - especially if it is first something casual like coffee. If you're more comfortable discussing it with him first then that is the right thing to do regardless of what I just said.

    Also, one a side note, I have two friends who married their friend's younger sister, including someone from my family. Good Luck!

    Ask the person has said above, I recommend you to see how it goes with her first before informing her brother as it may end up being very awkward. Good luck!
    • Very Important Poster

    Very Important Poster
    Ask him how he feels about being you being his brother in law?
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Updated: May 22, 2016
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