klookp Posted January 21, 2015 Posted January 21, 2015 I know this is an age old issue and I think a lot of people have had this kind of thing come up. I have been friends with him for about 7 years and met his sister around six years ago at college. I always thought she seemed like a nice girl, but didn't really start to think of her in a relationship way until a few years ago. But at that point, I was living 3 hours away because that is where I landed my first job out of school. At that point it was more of she was a girl I would like to date, but I was busy with other stuff and was considering grad school halfway across the country, so a relationship with her wasn't really on my radar, besides she is my friends sister and I am not even sure she likes me like that. I end up deciding against grad school and switch fields and move again work another job for more experience, which was still almost three hours away. Then a little over a year ago I got the kind of career job I had been looking for and it happened to be in their area. Once I had started hanging out with him and his sister more again, my interest in her sparked again. After a few months we went out to a bar in Chicago and we ended up slow dancing together, much closer than normal friends. After we were done she told me that she really wanted to kiss me. I didn't know what to say at that point and let it go, saying it probably would not be a good idea. Another month or so later we were at a bar in a group and I had gone to the bar to order another drink and she joined me a couple minutes later and we had a conversation and she then proceeded to kiss me on the cheek, something she had never done before. She thought she offended me at first but I told her it was alright and it just surprised me. A couple minutes later she was talking about how her brother always wanted us to get marries and I was completely thrown off by this. We looked at each other and she leaned in and next thing I know we are in a full make out session. A while later, my friend taps me on the shoulder, and we stopped. He wasn't happy at first, and was more mad at her than me, but the next morning he was more cool with it saying he was glad it was me and not someone else. Me and her talked about it, but didn't get into feelings, and since hung out, no awkwardness whatsoever. Me and my friend ended up renting out a condo together. Well in the last month things have reverted back to me and his sister getting more on the friendly side. It started off a few weeks ago with us talking, and she was drunk. She was worried about her appearance, and I told her she looked fine, and when she didn't seem to buy it, I admitted to her that I liked her a lot, and thought she was beautiful, and that she has a lot of great qualities. She gave me a kiss on the cheek and I thought about taking it a little further but I decided not to push my luck with her brother/my roommate the next room over. At that point she said she had asked her mom about us dating, which I guess her mom wasn't a big fan of because me and her brother are such good friends. Then last weekend, she was over along with some other people, and once again we were talking again. While people were in the kitchen, we were cuddling on the couch and I ended up leaning in and we had another little makeout session. Nobody saw us, and her brother knows nothing about it. I really don't know what to do in this situation, and really stuck and torn. On one hand, I don't want to piss him off, and I am not really sure he would be a huge fan of UA dating, but I think that has more to do with the worry of if something happened with us while we were dating like a bad breakup. And I am still not 100% sure on what her feelings are either. And I am worried about having that talk with her because I don't want it to turn into something awkward with us. At the same time, I don't want to sneaking around behind my friends back with his sister, plus it does me no good because I want something more out of our relationship besides casual encounters. Sorry for the essay, but I wanted to give a good background
Ebelskiver Posted January 22, 2015 Posted January 22, 2015 Go for it! It seems the brother has already given his approval-----better you than someone else. Tell her you'd like to start dating. Take her out for a real, official date. IF things progress and get serious have a discussion about what it would mean for everyone if you broke up, and agree to keep things above board and adult. But for now just get to know each other in a romantic way through dating. Be honest with, her, your friend and yourself. You're all adults. You can do this.
spiderowl Posted January 22, 2015 Posted January 22, 2015 Sounds like you need to talk to both your friend and his sister. You could try to avoid her and avoid your feelings but if you feel something more for her than 'she would be good for a fling', then it could be something great for you both. You are right to be concerned about a possible break-up though. Again, talk to them about that possibility and how you would all try to handle it if it happened. You could end up losing your best friend but then again people lose best friends for other reasons too.
Author klookp Posted January 22, 2015 Author Posted January 22, 2015 I guess one of my biggest concerns is that she doesn't want a more advanced relationship and I don't want to put myself out there and then there be awkwardness between us. Especially since she hangs out with me and my friend quite often. I guess you never know 100% how exactly someone feels about you until you talk to them about it
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