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She's my friend's sister. Should I tell her, first, how I feel about her? Or just go ahead and ask her out for a date?

Tagged as: Crushes, Dating, Friends, Trust issues<< Previous question   Next question >>
Question - (11 March 2015) 3 Answers - (Newest, 11 March 2015)
A male United Kingdom age 30-35, anonymous writes:

I've known my best friend and his sister for 3 years now. I'm 21 and they're 18. Throughout knowing them both my best friend is amazing and the nicest guy i've ever been around he is a friend for life. His sister is great too we're also very close. Their parents love me, they always say i'm their favourite out of my friends' friends and my mum loves my best friend and his sister, my mum wants me and my friends sister to get together shes always asking about her and hinting it.

I've liked my friend's sister ever since I've met her, I told her at the start that I liked her and she didn't say it back so we stayed friends which has been great.

However, it's 3 years later and my feelings for her have only got stronger as we've gotten closer. shes had boyfriends and i've had girlfriends but for me they were not her.

As for her everytime she was down or upset etc we always spoke she tells me her problems and I help best I can, she always says i'm a star etc cause I want her to be happy. I tell her she'll find a nice guy who treats her right and lately I've dropped her hints to try and pick up on but shes not noticed i don't think. we a talk all the time, text, call and even go out for coffee together and catch up as we're both at uni in different towns

I don't know what to do I really like her and believe theres something there between us but I don't want it to be awkward if she doesn't feel the same. Do I tell her how I feel or do I just ask her out on a date?

also before I ask her out etc I was going to ask my best friend if he's okay with it as I don't want to lose him because I want to be with his sister

View related questions: best friend, text

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A female reader, RubyBirtle United Kingdom +, writes (11 March 2015):

Just ask her out on a date. No need to have a discussion or "admit your feelings" before you do. Conversations like that are always awkward at the best of times and at worst, you'll feel like a complete tit if you've poured your heart out and she says "How sweet, but no thanks". Besides, if you ask her out on a date - I think she'll kind of get the idea that you're seeing her in a romantic light.

And don't ask her brother for "permission" first. It isn't the 1800's. I'd hate it if I found out that a family member had been given the heads-up on my potential romantic life. If the date does well and you both think you might be onto something, then tell him straight away.

But ask her first.

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A male reader, Denizen United Kingdom +, writes (11 March 2015):

Denizen agony auntYou have provided two alternate answers: "Do I tell her how I feel or do I just ask her out on a date?"

Perhaps there are other endings you should consider.

So often we crave for things out of our reach. Perhaps your feelings are amplified by craving something you can't have.

I say, 'can't have', because you have already waited three years, so something has been holding you back.

There is of course the issue of the young lady herself. Has she shown any interest in taking a relationship any further?

If it were as easy as asking her out why haven't you done it already? What's holding you back? You are 21, a man. Inside you must know what is right.

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A female reader, noerifbnwofbn United States +, writes (11 March 2015):

I think you should just go and tell her how your feel. honesty is the most important think in a relationship. if she still doesn't accept u, then u need to move on with your life. if she likes u then ask her on a date and if she says yes and the date go well and u want to keep going on dates with her then u have to tell her brother because if u don't, I can break his heart and you'll loose a best friend.

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