How to Strengthen Your Relationship/What do I make of this

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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
Hi Sara,

I know we can imagine his sister not being so excited about the two of you being together.  What if this is not the case though?  What if she would want the two of you to be happy and does not know your feelings for him?  What is the worst thing that can happen if you talked with her about how she would feel?  He may be thinking, "well.  I've hinted to her (you) so many different ways how I feel that she must not be interested."  Bottom line, I don't think we truly know what either are experiencing here and I believe it is worth investing a bit by checking it out.  Stuart

How to Strengthen Your Relationship

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Stuart A. Kaplowitz, MFT

Expertise

how to help relationship. How to address issues within relationship......I am pretty open here

Experience

20th year in the field. Managed and directed clinical programs. Now, I work out of my own office as well as supervise counselors

Organizations
California Association of Marriage & Family Therapists

Publications
The California Therapist

Education/Credentials
B.A. Psychology M.S. Counseling Licensed Marriage & Family Therapist

Awards and Honors
Hero of the Heart - Covina Valley USD

Past/Present Clients
I work with individuals, couples, families and children

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