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I'm sure he'll be supportive. You are already "in the relationship" - there's no turning back now - so enjoy it. Best, - Evan link Dating Advice for the 21st Century. Dating my best friend's younger sister? I am 22, my best friend Kyle is 24 and his sister Emily is Kyle and I have been best friends for about the past years and while I've always thought his sister was cute, I didn't do anything about it 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.
While it's not really up to your best friend whether you date his sister or not, if you' re any to not feel at least a little uneasy at the thought of you dating his sister. My best friend is dating my little sister - If you are a middle-aged woman looking to have a good time dating man half your age, this article is for.
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? What should I do?
Dunno it just feels like. Dec 29, Messages: Thez be doin da durty.
Dec 5, Messages: Feb 9, Messages: I would have already murdered him. By murdered, I mean written a strongly worded letter. Jun 11, Messages: I find my BFF's little cousin hot. I'll wait about a year before I move in for the kill. In the mean time I'll lay some groundwork.
Dec 6, Messages: No true friend would ever do that. He's not a friend. Jul 20, Messages: I am thinking your BFF is checking out your sis, but she might be telling YOU she's rejecting him to lead you to believe something other than the truth.
When you have them both present, ask something friendly like "You two datin' or what? They may be planning to murder you By murdering you, I mean play a joke on you.
Oct 20, Messages: First, he has to get your approval to ask her out. Feb 28, Messages: Aug 4, Messages: Talk to him, look at his intentions and hers. I wouldn't let it pass, it's a complicated situation.
Jan 28, Messages: All younger sisters are off limits until the age of Lay it down flat. Aug 22, Messages: No, it's man law. It's the equivalent of taking a piss next to a stall someone is already using. Lil Pun Contributing Member. Oct 6, Messages: How old are they? Let me clear some things up: You must log in or sign up to post here. Similar Threads - Dating Best Friend's. Would you let your Sister date one of your best friends?