Hey guys I’d like some thoughts on how to ask a girl out. I have absolutely no problem doing that, but I have one very touchy situation right here

Here it goes: The girl is a close friend’s sister… yep . I cannot really ask her to hangout (just me and her, even though she would want to) because, why would I suddenly start to hangout with her without my friend? My friend would probably be like “why the fuck aren’t you asking ME to hangout?! ”. At the same time, I don’t want to spend time with her behind my friend’s back. Btw I live in an apartment by my own and she lives with her family.

I don’t really care if I get the girl or not; I just want to make sure that I don’t hurt my friendship with the guy by trying to spend time with his sister. I know that if this girl is interested, our friendship will never be the same, but as you know the real regrets in life are the risks you didn't take.

I just want to spend time with her, chill and see if there is potential for anything else.
How would you proceed?
Any ideas?

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The people who are crazy enough to think they can change the world, are the ones who do.

So you are willing to sacrifice friendship just to see if theres a chance with his sister?

How about you just tell him straight up and try to figure it out like that? You WILL get caught regardless.

If you dont want to kill the bro-ship, tell him straight up like a man.

Tell your friend straight up. It will let him know your intentions and he will find out anyway. If you have good intentions there is nothing to hide, and he will respect your wish if he's a true friend.

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Attraction is a choice.
ITS YOUR CHOICE!
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I totally agree with you guys but I just don't see the point of telling my intentions if the girl is not interested! That's what I want to figure out.

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The people who are crazy enough to think they can change the world, are the ones who do.

So then be discrete in escalating with her, look for ioi's and once you're confident that she's interested, have a chat with your mate.

Either way, you're going to have to have that chat with your mate before it goes any further.

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New to the game!

My sister didn't used to have much of a social circle. She used to hang out in mine.

Twice she had a long relationship with close friends of mine. The first guy went behind my back and I caught them kissing. I walked away before I put the guy in hospital (that's how I felt at the time as it was such a shock, once the shock settled I could think more clearly). This definitely changed the relationship I had with this friend and as it happens these days we do not speak.

Second time, The guy called me about it. Though this was after he had gone behind my back. Again I felt uncomfortable but I knew this time that he was an awesome guy and would only be a positive feature to my sisters life and quickly got used to the idea.
However if he had just come to me before they went out he probably would have had my blessing from the word go.

So I fully agree with Makybe. Be discrete in getting your ioi's. Once you are really confident it's time to talk to your friend.

A lot of people say there are rules about going for guys family members and ex's.

If you do guy for your friends sister, even with his blessing, it might change your relationship with him forever. All cases are different though

Hope this helps

Scanner

Of course he wouldn't like it at first but my friend would probably get used to it because I'm pretty smart and I go to a really good university (also where he goes to school)-> I'm not a bad guy . However, the first thing I want to avoid is talking (seriously) to him about his sister and then figure out that she's not interested .

This is why doing just one small step behind his back (e.g. texting her to meet me on campus whenever I know she's near by or something like that) would not hurt too much. I've never hung out with her without her brother so maybe she would act differently... who knows.

Then, if I feel some interest, I'd go to my friend and tell him that I was thinking about hanging out (probably something more exciting than chilling on campus lol)
How does that sound?

_________________
The people who are crazy enough to think they can change the world, are the ones who do.

In your first post you expressed that you didn't care about getting her or not. Is this so? If this is correct then why are you bothering with such a messy situation.

However if you like her and this is very important to you... Yes you need to find out if she's attracted to you!
But calling her when she's nearby and other such actions might result in her saying to your friend "hey Northboy called me today / was hanging out with northboy AGAIN today". etc. If she likes you chances are that she wont do this.

If your friend finds out that you have been paying her extra attention whilst you are seeking your IOIs, he may very well ask if there's anything he should know.

I guess what I'm trying to say is that this could get messy and IS IT WORTH IT if you're that worried about your friends reaction?

What do you suggest?

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The people who are crazy enough to think they can change the world, are the ones who do.

Well what's more important to you? Your friend or his sister? Be honest!!

If it is his sister, then I would be wanting to continue to hang out with them both. Be the leader of the pack. Demonstrate that you are fun, have value, all the usual stuff. Be looking out for those signals, then tease if you get them. Reward in kind with IOIs of your own.

Like said before, if you become confident there is something there then speak to your friend. This is indeed a very touchy area and the greatest respect will be needed when having the conversation.

I'm sure he will be cool with it if you show him that respect by talking to him before making your moves on the sibling. It may be that you go for the sister, she's not into it and it will be awkward between you and her. But the relationship with your friend will remain - if he's as mature as you describe. I have been in your friends shoes twice and I really hope it turns out well for you.

Keep me posted