Moving Forward With My Friend's Sister?

So I mentioned a bit of a month ago that I had been interested in my friend Victoria's sister, Kaelyn. Victoria, wanting to help, proposed the idea to Kaelyn a couple days ago that maybe she and I should do something together. Kaelyn (to my disbelief!) actually agreed and texted me asking if I wanted to watch movies with her this Saturday at her house. Naturally, I accepted her invitation! I was so excited for today!! Since the last time I saw her a couple of weeks ago, we had texted everyday. I really felt like we were bonding as I had hoped! Anyway, when I got there, she greeted me as I entered, made us some popcorn, and put the first movie in. It should also be noted that Victoria was also there watching with us, though my intentions were to spend the day with Kaelyn. This wasn't a problem for me or anything because I still had lots of fun enjoying both their company. However, after the first movie, Kaelyn left both of us to conduct activities elsewhere- by herself. This confused me, but I never said anything. I continued watching movies with Victoria until it was time for dinner. This was the first time Kaelyn had gotten off the computer to join us again. Afterwards, she went back to her PC while I continued to be with Victoria. I didn't see her again until the very end of the night (I was there about 10 hours) when she said her farewell at the door. It should also be noted that only Victoria actually walked with me to my car when I left.

This was Kaelyn's tweet afterwards:

"my sis and her friend are watching HP; he hasn't seen it before"

I asked Victoria what she thought about the experience when I got home and she gave me her hypothesis:

"You were introduced as my friend from school so she interacts with you, but you've been dubbed more of her sister's friend then her friend. She's a bit dense, you'd have to outright say that you hope to be as good a friend to her as you are to me."

As you can imagine, this is an endeavor I will have to overcome- somehow. I am very serious about growing close to Kaelyn and I do not want her presumption to prevent that day from arising. So my question would be, what am I to do? We are both somewhat reserved/ timid people so I definitely want to be as natural as possible about it. So, what would you advise I do in this situation?

I personally don't think it's a good idea to go out with your friends sister. If you want to take the chance then you should ask Karleen if she wants to go out for a coffee sometime.Have fun and talk her and see how it goes -also make sure you have the best intentions with her because if things end badly , It may put a strain on your frienship with Victoria

I think you are over analyzing things. Too much thinking and not enough allowing things to happen naturally. It likely comes across forced and not genuine. Be fun and young.

OP, I have dated my friends sister before and it got to be a very serious relationship. We also went through a hard breakup though because she was keeping a dark secret from me and her family...

There is NOTHING wrong with you dating your friends sister whatsoever. In fact, you can have a great relationship with someone like that because you take dating a friends sibling more serious than a freak off the street say you will. Just have a couple ground rules set in place...

1) Not that this should matter, but I would ask you friend (Victoria) first if you two can date. It sounds like she already kind of put this in motion anyway. But I would never ask someones sibling out I am a close colleague/friend with without alerting them first. I remember in my friends case I thought he would be mad/hate my guts if I pursued his sister. He did not, he was perfectly fine with it.

2) Keep your relationship separate from you friendship. No matter what happens, don't let angst/drama from your possible future romantic relationship interfere with your friend.

3) Be serious. This is not a "one night stand". If you are going to pursue your friends sister, it should be because you think she is a serious, potential partner for you. Someone you can fall in love with. If you are not doing this for the possibility of falling in love, then don't do it. Your friend would probably hate you forever if you tried to use her sister for a hookup.

3) Be willing to accept that you may lose your friend if things don't work out. In my case, fortunately it didn't. But know sometimes when break ups happen there is serious bitterness from both ends. This Karleen could explode and exile her sister from ever talking to you again. Women are unpredictable!

Good luck.

Well, I don't know, sounds to me like this girl isn't that interested in you because why did she just leave and spent no time with you at all? However, it also looks like she has no idea you like her. I think you should ask her to hang out one-on-one. Don't just go to their house, but invite her out somewhere, like dinner or movies. I think you need to make it clear you are interested, otherwise you'll friend zone yourself lol Work your magic man!

I was talking with Victoria some more about this. First, I would like to address a few comments:

1. I am indeed interested in having a serious relationship. I do not treat dating as some kind of game, but as a special connection I can have with another individual who I support and care for deeply.

2. Victoria does not mind if I date her sister and is even helping me gain information about Kaelyn's feelings towards me. She believes that we have much in common and would be able to have a long-lasting, healthy relationship.

3. I have no idea why everyone has referred to her as Karleen. It's Kaelyn. XD

What I have been told by Victoria (regarding Kaelyn's thoughts) is that I am still more Victoria's friend than her own, but she definitely enjoys my company. To combat this, I am going to attempt going out one-on-one with her so I may make my intentions clear. She is a scholar of a person, so I was thinking the library or bookstore. Also, I am going to try acting around her as I would around anyone else to make things flow more naturally. I want her to see me as who I truly am, even if that person is a bit socially awkward ^^

And what happens to your friendship with Victoria should you and her sister date...and break up?

I cannot say for certain, but it is not something I am fretting over. I would never date anyone that I did not have the intention of being together with indefinitely.

What a load of crap.

I don't really understand what purpose you mean to serve. This is meant to be a helpful forum so would you kindly move your negative comments elsewhere?

My brothers best friend wanted to date me towards the end of highschool.

I told him he had 2 choices...he could date me, one day we would break up...and my brother and he could no longer be friends.

Or, we could choose to not let our hormones rule our lives, he could remain my brothers best friend...and we could be friends for life.

We chose...friends for life. He married a high school sweetheart. He and my brother still, 30 years later are friends. And I see he

I'm 1x-3x a decade.

I cannot say for certain, but it is not something I am fretting over. I would never date anyone that I did not have the intention of being together with indefinitely.

What? You are going to propose marriage to every woman you date? Until one finally agrees?

I thank you for your observation and acknowledge that possibility. Despite that, I feel strongly enough about this that I will continue to pursue it. Not because I "am ruled by my hormones," but because I desire to be in a loving relationship with someone that shares many similar values and interests. I am adamant about my decision.

I am 16. Why would I be proposing to anyone?