Would like to date sister of a girl I slept with

[dynex]

Hey guys, really sorry for the long post, but it's a bit of a long story...

I've known these sisters for many years through family friends, but never really got to know them well. Fast forward to about a year and a half ago, I saw them both at a mutual event, where sister A (the one I currently like) was with her bf; and sister B (the one I eventually slept with) was hitting on me all night. Sister B and I exchanged numbers and went on about 4 dates over the course of 2 months (texting often throughout), but nothing ever materialized. Not even a peck on the lips.

We eventually lost touch and she expressed that she wasn't looking for anything serious and didn't want to lead me on. We didn't talk for about 6-8 months after, but saw her at another event where she plain out came and made out with me (which I reciprocated). After talking for a week or so, I told her I thought it would be best we go our separate ways and remain friends, as I was not looking for a "friend with benefits".

Later on that month, I wished sister A, a happy new year on facebook (since we do know each other), and we began to talk on and off for a month. The convo was light but entertaining and it was nice getting to know her. Naturally I wanted to get to know her better, so I asked if she wanted to grab a coffee and catch up. She regretfully declined saying that while I was fun to talk to and that we would prob have a great time, she felt a bit awkward about it, because of her sister.

I assumed she knew about the make out, so I told her what my intentions were (just catching up), but if she was uncomfortable about it, I would respect that and there would be no hard feelings. I then kept my distance for another 4-6 months.

One random night I spoke to sister B in passing to see how everything was (remember we ended the fling on good terms), which led to her offering me sex with no strings again. I was admittedly lonely, horny and felt that all possibilities with sister A were gone, so I decided to go for it. We slept together that night and texted each other on and off for about two weeks. At one point, we both just stopped texting each other and haven't spoken in a month.

Now, a few days ago, I was at a bar and ran into sister A. We started talking and had a fun night catching up, which I asked for her number. She gave it to me and I jokingly asked if we could now go for that coffee. She immediately said to message her. The rest of the night went great (touching my arm whenever we spoke, looked for me whenever we weren't) and I could tell she enjoyed hanging out with me.

All this to say, I've always been really attracted to sister A (beautiful girl) and always felt our personalities matched better than with sister B. I just never tried since sister A was always taken. But now I'd really like to get to know her more, as I feel like we would definitely hit it off.

In my opinion, I don't see an issue with sister B, as we both always knew nothing would come out of it and only slept together once. I just don't want to lose out on an opportunity to get to know a great woman because I had a past with her sister. Especially since I feel like she always just had a physical attraction for me and nothing more; despite her saying that I am a great catch for anybody.

I have yet to message sister A, but really want to. I was thinking of being up front with sister B and expressing my intentions with her sister. I don't want bad blood between them and wouldn't be pursuing this if I didn't feel like it was worth it. What are your thoughts guys?

[specialmom]

Yes,, this is an old post.  Best to start your own which you can do by going to the top of the page and hitting ask a question/ the orange button.

I probably would not be interested in someone that slept with my sister.  Yuck.  There is a whole wide world of people out there, not sure why people limit themselves in such a way.  good luck

[Help4256]

hey I  know this conversation is old. but hopefully you get this! My youngest sister has slept with a friend a few times. I was not aware. I asked her if she had ever slept with the guy before we started hanging out, and she said no and he said no. He has always been a friend of the family. When we hang out its been lots of fun, then I found out that he did sleep with my sister. He lied she lied, I understand why both did lie.  I have not slept with this guy or hooked up. He seems to like me asking to hang out, and we have a good time. I am just so confused and grossed out !! but I like him its so weird. Then again my younger sister has  been with a lot of guys and majority of them are ones that I dated first or liked. So weird.... What are your thoughts on all this? how do you think the guy feels?? will he always be thinking about the times he had sex with my sister when he is around me ??

[RockRose]

I know two couples that are like this - the couple that "stuck" was the second sister.

In both cases,  though,  the first sister rejected the guy.  

This is different from your situation - Sister B,  from what I can tell,  would like to have a relationship with you if you were willing.

Dangerous territory, IMHO.

[Chima7]

Just a couple of things to add. I don't think it's unusual if she hasn't told her sister about sleeping with you. I'm really close with my sister but she doesn't know about any of the guys I've slept with. She may assume based on relationships I've been in, but we have never had a conversation about sex. Ever.

Secondly, I agree with the other ladies here that I would be completely weirded out to date a guy my sister slept with. And there's no way she wouldn't find out because if you guys got serious and you started showing up at family parties then the cat would be out of the bag really quickly. Just for the record, I've asked several of my female friends and they too would be grossed out by your idea to date the sister of a girl you've slept with. Conclusion = Sister A would have caught on eventually and you'd be kicked to the curb once she found out. Or, if you told her you slept with her sis but does she want to date anyway -- she definitely would have said Hell to the No!

[specialmom]

That is a good point life.  I may hang onto that quote and use it at a later date!  LOL

[dynex]

haha definitely! But it wasn't the case, as she was the driver that night. I just think her uneasiness about the situation was temporarily forgotten in the moment at the bar and when she had time to think about it, decided not to pursue it

[Life360_Dave]

Sometimes alcohol can affect logical thinking.

[dynex]

Hey guys, here's an update:

Messaged A yesterday and had a brief text conversation that spanned over a few hours. Her responses were kinda friendly, but short and not very engaging. Definitely not the same vibe of that night at the bar, at all.

I suspect B might have spoken to A and now she's just being polite. Either that or I caught her on a bad day? Either way I'm gonna let things settle and give both space for the time being. I don't want to push too hard and get burned.

[Life360_Dave]

Like i said you are on the rebound with A and this could be a big let down when its all said and done.

[nursegirl6572]

I agree with the advice you've been given.

I don't think you have an obligation to tell Sister B anything at this point, just be very honest with sister A, and express that it is what it is with sister B, that you like her, there just wasn't relationship material there for either of you, in your opinion.  You could ASK sister A if she thinks you should have a discussion with B.  

Don't try to mininize it, elaborate a whole lot on it, just stick with the basic brief facts, and explain that you really like her (A), and want that to be all out in the open before trying to get to know her.

It's a crap shoot for sure, and I'm of the camp who would never consider it, it would be just too weird on too many fronts for me.  You never know though, like sm said, there's all kinds of people in the world, and this girl may be willing to work through that to get to know you better and give you a chance.

I think you're smart to at least acknowledge that it's an awkward situation, and I think it's a mature approach to want to respect the feelings of both sisters.  

Good luck to you...update us, I'd be curious to hear how this turns out!

[dynex]

I agree. No matter what, even if sister B were to tell me to keep it a secret, I wouldn't feel comfortable having that hidden moving forward.

I also agree with you Life360 about her possibly already knowing. I feel like it would be strange that one sister hides it from the other.

Trying to tread carefully, as I don't want my intentions to be misinterpreted. Should I feel that A has any form of interest, I will speak with B and see how she feels about it. Which will then follow with giving full disclosure to A. Or should I just speak with B before anything to avoid any possible misconceptions?

[Life360_Dave]

I think as long as you tell A about B its ok and she most likely knows already anyway as sisters can be close. But remember you are on a rebound now and maybe her intentions are the same as B with you.

[TTinKKerBBell]

ditto SpecialMom
You must tell Sister A up front about Your encounter with Sister B

This could be touchy for Sisters

It could kinda, sorta feel incestious to one Sister or the other, maybe even Both.  Either, or - it wouldn't make any difference 'which' Sister might feel that way - They remain Sisters - You are the outsider - and if either One of them should feel that way it would be Their's to deal with.

[specialmom]

Well, give it a try and tell her the truth beforehand.  She may have no problem with it.  I'm just saying . . .  I would.  It would have nothing to do with you but that I view the world as FULL of people and I don't want to be with one who's done the deed with my dear sister.  That's not to say all women are going to respond that way.  

So, tell her the full truth and see what she feels about it and go from there.  good luck

[dynex]

Hi thanks for the quick response! No I definitely own up to going through with it. I admitted to being the prototypical horny, lonely man, who accepted the offer; and are as much to blame than sister B, if not more.

I agree that this may just end up being a recipe for disaster, but from what I've seen with sister A, if feel like it is worth being open and honest with all parties and see where the chips lie. If she's not comfortable with the idea of dating me after that, then I have no choice but to respect that. It's logical but unfortunate, since I really do feel like there could be something there.

Again thanks for your thoughts!

[specialmom]

Well, sister B slept with you and you presumed no strings attached, right?  Only thing is, the string attached is that her sister will be less interested in you if she is a healthy thinking girl.  I would never want to sleep with someone or date someone that had a sexual encounter with my SISTER. There's guy code and then there is girl code.  It is hard to get out of your mind that the person you are with once (even if it was only once) was naked with your sister.  

And, you were chatting up with the one sister when the other 'offered sex'.  (you make it sound like it was all her idea by the way which is not really owning your share of the situation).  

Anyway, my motto is to steer clear of drama and a potential sister triangle is drama big time.  If sister A isn't aware that you spent the night with sister B and finds out later, sister A will be mad.  Does sister A know?  

I guess you can say to sister A that I slept with your sister (and really, don't make it sound like she is some kind of hussy for it as YOU did it too which makes you an equal hussy) and see what she says.

I wouldn't want to date you after that personally.  Not that you aren't a nice guy but just because that would wig me out to date someone that my own flesh and blood had been intimate with.  Others have different standards and are more willing to take a risk (as this could blow up later if actually sister B kind of like you, knew you didn't really like her so gave up OR if she decides to get jealous now for some reason . ..   just makes things really awkward . . .  not to mention if sister B tells the mother of both girls who then is like "ewww.  yuck!". )  

It's just a complicated scenario and I wouldn't get your hopes up that it will work out.  good luck

[dynex]

I forgot to mention that sister A and her bf broke up a few months before I wished her happy new year