Dating my best friend's younger sister?

I am 22, my best friend Kyle is 24 and his sister Emily is 19.

Kyle and I have been best friends for about the past 5-6 years and while I've always thought his sister was cute, I didn't do anything about it...cause he is my best friend. I've always known she has found me attractive not only from the way she looked at me, but because Kyle would even joke around about it.

Anyway, about 2 months ago Kyle and Emily came to visit me (I live by myself in an apartment) so we could hang out, drink, etc. I ended up making out with Emily and we both discussed how we really felt this connection. Kyle was off grabbing some other friends at the time that's why he wasn't there.

Anyway, Emily and I have kept in contact. We have gone on dates, held hands, kissed, and had sex several times. Sex with her is the best sex I have ever had. We discussed what we should do and we realized we had to tell Kyle. I told him on two separate occasions that I was hanging out with his sister and that I like her. He didn't seem to care at all. He is not the overprotective type, but he didn't seem to care even a little.

So Emily and I still hang out. I'm a bit wary of what her parents are going to think. I know they really like me, but I haven't told them and neither has Emily or Kyle.

I'm not even sure about this whole situation. Emily and I really like each other. It's not just some random hookup. We get along really well and we have a great connection. It's just obviously different cause this is my best friend's sister.

Furthermore, Emily has been telling me recently that I am "hard to read" which I am assuming is code for "I'm not sure where I stand with you" or "Are we going to be boyfriend and girlfriend yet?"

Help? What should I do?

What can I do about their parents?



Most Helpful Guy

  • If you're serious about wanting a relationship with her then:

    1) Ask Kyle if he's cool with you dating his sister

    2) Tell her you want a relationship with her

    Don't worry about the parents, they will be happy if you're boyfriend/girlfriend and you treat her right.


Have an opinion?

What Girls Said 3

  • Chill out. Now really think about it. There's NOTHING wrong with dating your Best Friends sis. (I married my bro's best friend and it's been nearly 26 years now!) There's NOTHING wrong with telling the parents. Chances are if they've seen you together they prob won't be surprised to know your dating. You're both adults and can and should do what you feel is right and not let others order your life...but they don't sound like the sort that would...I really wonder if you're feeling some guilt about the sex? Sex always seems to complicate things. Not that it's wrong and no I'm not one of those females that hates sex...there's just plenty of good reasons why it's best saved 'til marriage. (We almost made it. LOL We were engaged but I wish we'd have waited.)

    Don't throw away a good thing here dude!

  • Well if you both share the same feelings this is a good thing, and your best friend will understand but it might feel a bit awkward for him and I suggest you don't hurt his sister or I'm pretty sure he WILL kill you or put you in the hospital. You always have to be careful with parents but if they like you and they know you truly care and you aren't going to hurt their daughter they will accept it. And Emily is probably wanting you to be her boyfriend and wondering if you are having second thoughts about being with her. Just try to spend time with both her and Kyle , because if you spend more time with Emily Kyle will feel betrayed.

    hope this helped

    good luck

    god bless

  • usually when a girl says your hard to read she wants to know what your thinking, about her and the situation; sometimes even to know where its going, not necessarily if you are boyfriend/girlfriend yet, but will you be... as for the parents, I think that should be Emily's job... she could mention you in a coversation, casually discuss something about you or that she likes hanging out with you...


What Guys Said 3

  • Hey,

    I would put Emily's mind at ease and go out with her. It's what you want and it's what she wants. I wouldn't worry to much about her being your best friend's sister because he's cool with it. But, I'd have a convo with him letting him know how you feel about her and telling him your intentions on going out with her. I'm sure he'll be supportive.

    You are already "in the relationship" - there's no turning back now - so enjoy it.


    - Evan | link | Dating Advice for the 21st Century

  • when a woman says "you're hard to read" it means "I'm confused but I'm making you responsible for my emotions because I'm too passive to communicate like a mature adult."

  • You Dog lol