General Dating Questions/what to make of this

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Question
So I've been best friends with my friend for fifteen years . I've know her brother for same time and last few years I've been having on and off feelings. Mostly off because I make myself forget it cuz I feel that it could never happen
Cuz his sister is my best friend. Well Im single and he broke up with long term gf over a year ago and I just can't
Shake the feeling he feels the same but also won't say anything cuz of his sister.

We went on vacation recently and he just constantly teases me , but at one point he said he liked my outfit which
Made me smile. I mean it could mean nothing , friendly sisterly thing. He pokes at me hits me all this stuff and tells me how much he hates me for last fifteen years blah blah. But then his sister goes "u know u say all this but you're the only one that  keeps trying to come up with solutions to get her to go on vacation with us when she cant cuz of work. Then we're going on vacation in a couple weeks again and he's like yeah it's gonna be5 against 1 I'm gonna get everyone to be on my side against you! He always laughs and jokes . And then I was telling him how this girl was being mean and he's like hey if anyone bothers you, you let me know ill take care of it! Then his hair was messed up and he's like "Sara, can u fix my hair just run your hand thru the top." Then someone asked if I was his gf and he was like "she wishes!"

I guess what confuses me is we were talking about high school and he's like "hey you never gave me a ride to school what kinda sister are you!?" And that totally threw me in for a loop. His sister has had to tell him to stop flirting with me and vice versa and when we go out she'll pull me away from him cuz it "kills his game" but he pulls me right back. He doesn't tease other girls or even his sister. His dad told me out of the blue that he only does this with me. Gosh idk what to think. I can't tell his sister I would want him to do it . He doesn't know I have feelings for him

Answer
Well it does sound like he likes you if even his own father says he doesn't act this way around other girls. I can't tell you if it is a good idea to persue this however. I don't know the risk that this might affect your friendship with your best friend.

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James

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First and foremost if you read ahead you'll find I have a word limit on questions I'll read. This site is for short simple questions and it should not be for writing essays. Please also note I am unfamilar with most cultures outside of United Stated, UK, and France. Please respect my rules. I don't like rejecting questions. I will be the first to admit that I don't know everything about dating, women/men, and interpersonal connections. However I have learned quite a bit vicariously from other people's experiences. Think of my advice as a second opinion. I would be happy to answer all questions related to relationships, dating, self-confidence, and self-image that I can. I have struggled with all of those things and probably know better than most how to deal with all of them.

I hope more than anything that my advice and opinions will help give people perspective in their lives, and hopefully make them feel better about themselves and their situations. I will attempt answering questions for anyone of any age group or nationality. However it would be particularly useful to know the age of all people involved. It does make a difference towards the advice I give. Also not terribly familar with arranged marriages and situations in which the family can dictate the details of the relationship.

My Rules:
1). I can't answer questions that ask if a girl or guy likes the other (very difficult to know remotely)
2). No questions that are More Than 250 Words. I understand that problems can be complex, but there is a real limit to how much I can read and fully understand. Particularly if English isn't the questioner's native language.
3). Only questions from Americans, Canadians, British, and cute French women.
4). No questions that ask the meaning behind if a person sets their FB status to single, coupled, or private or if they still have a dating profile undeleted somewhere. If you're cyber snooping you're likely the issue.

Experience

I don't really have any specific experience in this area other than learning from other people's mistakes and a few of my own, and whatever I've learned as a psychology major.

Education/Credentials
B.S. Psychology

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