Should I continue to sleep with my best friend's sister?

November 5, 2009 7:05 PM

Should I continue to sleep with my best friend's sister?

Ok, I've asked quite a few of my friends, and they all seem to think that what I'm doing is OK.

So my best friend and coworker and I became very close after each of us got divorced, and we did have a brief relationship for a time. But she said that she wasn't interested in that kind of relationship with me. I was hurt, but I moved on, because I enjoyed spending time with her so much.

So we transitioned into a semi-platonic relationship (occasionally we kissed a little when drunk), and it remained that way for several months. And then her sister came to visit for several weeks. So my friend invites me out with both of them, and all three of us proceed to have a rip-roaring good time that evening. But it's obvious there's tremendous sparks between her sister and I. So we're sitting around my place, and her sister keeps trying to kiss me, and eventually I get into it. But nothing really happened that night.

But we'd exchanged phone numbers, and I talked to my friend, and she said that I could see her sister, but that any of the tomfoolery that we had been doing (I'm assuming the occasional kissing) would have to stop, which I was fine with.

So the sister and I keep texting and eventually we went on some dates and slept together.

So my friend completely freaks out and won't talk or look me (which is a little awkward at work). She says I completely broke her trust. Now her sister lives in a different state, so it's not like our time together was anything serious, more like a lark of two people very attracted to each other.

So her sister is coming back into to town next week and wants to see me. Should I see her?

I'm very interested in the sister, and I think, my friend should be OK with it, because she DOESN'T want that kind of relationship with me.

What should I do? Should I continue to see her sister?

posted by anonymous to human relations (59 answers total)

What should I do? Should I continue to see her sister?

If your desire to see her is greater than your desire to avoid drama, sure.
posted by The World Famous at 7:11 PM on November 5, 2009 [1 favorite]

No, you shouldn't see the sister.

There are two rules in life: (1) don't date co-workers, and (2) don't date the siblings (or parents) of people you have previously dated.

You broke both of these rules.
posted by dfriedman at 7:11 PM on November 5, 2009 [6 favorites]

Your question as presented doesn't explain why your friend is so upset. There must be more going on here. Maybe your friend hasn't told you something important, maybe she has but you don't realize it's important, but as presented here the situation makes your friend sound completely arbitrary and irrational. Is she? Or are you not making some kind of connection?

Good luck.
posted by amtho at 7:12 PM on November 5, 2009 [2 favorites]

I'm going to be a bit contrarian here: your friend specifically said she doesn't want to date you, continues to hang out with you because she thinks you're a great guy, and then introduces you to her sister where booze is involved. What the hell did she think would happen? She passed up her opportunity to date you and doesn't have the right to be jealous now.

My answer would be quite a bit different if you and the original friend were longtime platonic friends, she was male, and you had grown up together: that's a situation where you just don't date "friend's little sister", period. If the friend is going to be irritable about the whole thing, she needs to either (a) save it for her therapist or (b) explain to you what exactly her problem is, not give you the silent treatment.
posted by Inspector.Gadget at 7:17 PM on November 5, 2009 [7 favorites]

Do you want to poison the sister's bond and family dynamic for, possibly, years or decades to come because of a lark of two people very attracted to each other.
?
No? then don't see her. Unless you are entirely serious about the sister and willing to slog through all the drama with the two of them, knowing what damage you've already done, and what further damage you can do, then no, it is entirely not worth it.
You may change jobs or move away, but they are always going to be sisters. Consider that first.
posted by Cold Lurkey at 7:21 PM on November 5, 2009 [1 favorite]

you began the hooking up with her sister process while you were still making out with you. they will tell stories about what a douche you are for years to come. cold lurkey is totally correct - you should step out of this for their sake. there are plenty of drunk funny girls to sleep with casually without out having to dip into the company's pool or the sisters of former hook ups.
posted by nadawi at 7:25 PM on November 5, 2009

I think your friend's feelings are all the following: irrational, unfair to you, and understandable. In other words, she's not messed up for feeling how she does, but it's the sort of situation where she ought to deal with getting over herself instead of imposing weird rules on you and her sister.

But people don't always do the mature thing, and you can't make your friend change her feelings. Assume her feelings won't change: it's up to you to decide whether you want to retain this friendship, or see her sister. Because whether or not you're right -- or an informal poll of your friends and the internet says you're right -- isn't going to matter to your friend. You might decide you value the friendship more than seeing the sister, or you might decide you don't want to be friends with someone who acts like your friend does. Really, either option is reasonable, I think, and depends on the relationship. But don't try to convince your friend she's wrong because it will probably make things worse.
posted by Nattie at 7:25 PM on November 5, 2009 [1 favorite]

Ok, I've asked quite a few of my friends, and they all seem to think that what I'm doing is OK.

So why are you still asking? Why are you so desperate for approval on this? This is your personal life, it's no one's business but your own. Make your decision and live with it. That said, if you really want my opinion, I think the whole thing is a lot more trouble than it's worth. It can't be that hard to find some other cute girl to sleep with.
posted by ThePinkSuperhero at 7:26 PM on November 5, 2009 [1 favorite]

I'm not sure how you plan on "continuing" to see her if she lives out of state. It sounds like you are asking for validation to have a one-weekend stand in defiance of your friend.

People can be weird about being close (your word) to someone, and then having that someone become closer to someone else they may be equally close to, especially family. Everyone's different. You should be free to see anyone you like, but your friend did ask you to not pursue that avenue.

Something tells me that there's more to what's between you and your friend than you let on - whether you realize it or not - that would cause her to not want a relationship with you, but be so adamant about also not wanting you to have one with her sister. Either she's jealous but afraid to tell you, or she's worried for her sister in regards to something about you, and afraid to tell you.

If you wish to gain back respect of your friend / coworker, make it clear that you're sorry that things went the way they did before, but you value your friendship and work relationship more than a weekend fling, and invite them to dinner again. Don't let anything come of it... let them meet you somewhere, have a good time, say your goodbyes, and let them leave together.

But if you decide you want to pursue things with her sister, which you are perfectly entitled to as long as the feeling is mutual, then just be prepared to lose that friendship. Whether or not she's acting rationally is irrelevant - what is relevant is the outcome and which one you are willing to accept.
posted by SquidLips at 7:29 PM on November 5, 2009 [3 favorites]

"But we'd exchanged phone numbers, and I talked to my friend, and she said that I could see her sister, but that any of the tomfoolery that we had been doing (I'm assuming the occasional kissing) would have to stop, which I was fine with." and then "So the sister and I keep texting and eventually we went on some dates and slept together. So my friend completely freaks out and won't talk or look me (which is a little awkward at work). She says I completely broke her trust. Now her sister lives in a different state, so it's not like our time together was anything serious, more like a lark of two people very attracted to each other." don't make any sense. What happened between the time you asked your friend if fooling around with her sister was alright to her getting upset over it?

Personally, if I had pushed you away it would have been because we were co-workers, even if I really did like you. If you then came on to my sister I'd be wary if it was serious and possibly assume you were either trying to get back at me or were just being a sleezeball.

Regardless of if this is "right or wrong", you should find someone besides a female co-worker/best friend that you've had a relationship with and her sister to fool around with. There are plenty of fish in the sea. The girl doesn't even live there anymore. Is it really worth completely violating your friendship with the person that even allowed you to meet this person?

Does this sister know you had a previous relationship with the other one? Does she know her sister is mad at you because of this? If she does and she's still willing to do this despite your co-worker/her sister's acknowledgment that she is not pleased with it, perhaps you two are meant for each other.

My answer would be quite a bit different if you and the original friend were longtime platonic friends, she was male, and you had grown up together: that's a situation where you just don't date "friend's little sister", period.

On preview, why is this acceptable behavior on a man's behalf but not a woman, or why do you have to be friends forever? I'm going to assume that the co-worker came to her senses and realized that being in a relationship with a co-worker was probably a terrible, terrible idea. While it might not have been great judgment to take her sister and the OP out on the town, it still just reeks of something I would shake my head at both of them over.

Perhaps she feels like the OP's friendship with her was replaced by a sexual relationship with her sister. If my sister were coming into town to screw my co-worker that she met through me instead of spending time with me.. or made it awkward for me to be around the two of them when we had so much fun before this ended up going down, that's just not fair and I think she has a right to be upset if that were the case.

But it's your life. If you don't have a problem with making a co-worker upset and possibly fueling family drama, go for it.
posted by june made him a gemini at 7:31 PM on November 5, 2009 [2 favorites]

Relationships always seem to be about wanting control over another person, and end in sadness when you realize the only person you can control is yourself. Your best friend is trying to control who you can and can not see. This isn't right and you should be able to see her sister if you both want to, however YOU cannot control how your friend feels about it if you do. You don't get to tell her her feelings are 'wrong' no matter how awkward it gets.

Feel free to see her sister, but understand you cannot make any judgements or exert any control over your friend, and you may lose that friendship because of your actions.

I'd see the sister if it was me, I think.
posted by spatula at 7:31 PM on November 5, 2009 [1 favorite]

Of course you should see her.
posted by spaltavian at 7:32 PM on November 5, 2009

your friend specifically said she doesn't want to date you, continues to hang out with you because she thinks you're a great guy, and then introduces you to her sister where booze is involved. What the hell did she think would happen?

Exactly. When you throw fish back into the sea, you can't control where they swim.

So my friend completely freaks out and won't talk or look me (which is a little awkward at work).

Well, that ain't gonna do her a lot of good at her next performance review.
posted by rodgerd at 7:43 PM on November 5, 2009 [1 favorite]

Do you value your friendship more than your "spark" with your friend's sister? if so, no. if not, yes.
posted by kylej at 7:44 PM on November 5, 2009

I'm very interested in the sister, and I think, my friend should be OK with it, because she DOESN'T want that kind of relationship with me

What you think your friend "should" be and what reality is are two different things. You can wish it different as much as you like, but human emotions are what they are, not what we think they ought to be.

You have three choices: dump the sister and try to repair your relationship with your friend, dump your friend and go with the sister, or back out of both friendship and relationship. Wishing it is otherwise won't help.
posted by Ironmouth at 7:44 PM on November 5, 2009 [5 favorites]

No, don't see the sister. Is it really even worth it? There will be other girls who aren't related to your friend.
posted by SkylitDrawl at 7:47 PM on November 5, 2009 [1 favorite]

This sisterdrama will go on for decades. Please don't feed it.
posted by marble at 7:51 PM on November 5, 2009 [3 favorites]

Ok, I'm the original poster, so I'm going to add some color.

Both women are irredeemably smoking hot, not that that should matter I guess, but it does.

I've had a crush on my friend for over a year, so it was very difficult for me when she said she didn't want that kind of relationship with me. I didn't and still don't know how to transition to the type of relationship she wants me with. I thought (and this is probably just little head thinking) that this would make it ok for me to just be friends with her, since that's what she wants.

My friend and her sister also have this weirdly competitive relationship, they're not super close.

I know I met her sister through her, but our (me and the sister) relationship really took off. She fantastic, beautiful, funny, smart, and she WANTS to be with me.

At this point, I think we're both at loggerheads, I will continue to see her sister (her sister comes up several times a year), and either she comes to grips with this or not. My friend has told me that her and her sister's relationship is fine, it's just me that she has a problem with.

I don't know what exactly I'm looking for with this question, validation maybe? I generally think of myself as a nice guy, but this kind of has me feeling slimy.
posted by aloysius at 7:54 PM on November 5, 2009

There's a phrase for this situation: Don't shit where you eat.

There are plenty of other women to get attracted to that don't come with weird, potentially job-threatening drama. Go find any of the number of them. It isn't as if you've invested emotionally in the sister.
posted by axiom at 7:57 PM on November 5, 2009 [1 favorite]

Do they look alike or something?

My friend and her sister also have this weirdly competitive relationship, they're not super close.

Seriously? Please stop it. They could be resentful of one another over this little incident for years to come. YEARS.

At this point, I think we're both at loggerheads, I will continue to see her sister (her sister comes up several times a year), and either she comes to grips with this or not.

Oh. Okay. Looks like you've made your decision. I can't exactly validate it, though. I think you're headed for a mess, but y'know, live yo' life, broseph.
posted by SkylitDrawl at 8:03 PM on November 5, 2009 [4 favorites]

I think based on that she told you before that it was ok, then it's ok. She'll get over it, either because it won't last with her sister, or because it will last with her sister.
posted by singingfish at 8:04 PM on November 5, 2009 [1 favorite]

I would be totally creeped out if someone I used to make out with started hooking up with or sleeping with my sister, even if I wasn't friends with that person.

I agree with marble that this sounds like a big ole pot of drama, and maybe that's part of the attraction for you. I'd guess that her problems with it stem from her relationship with her sister and don't really have anything to do with you. But I'd recommend that you avoid stirring the drama pot.
posted by emd3737 at 8:04 PM on November 5, 2009 [1 favorite]

Relationships between siblings can be very complicated. And if they are competitive, as you said, your best friend probably feels like she's going to "lose" you to the sister, or that you'll become closer, etc. You are supposed to be her friend, not her sister's.

It doesn't sound like your best friend is really your best friend in your mind. From what you've written it sounds like you wanted her to be a girlfriend, so you've been biding your time hoping something will change. And perhaps this situation with her sister feels like a bit of "see what you passed up?" Have you really analyzed your motivations in this little domestic drama?

It seems to me that if you really were best friends 1) you would put her feelings first over getting laid and 2) you'd be able to talk about this situation, even though it's uncomfortable.
posted by witchstone at 8:06 PM on November 5, 2009 [9 favorites]

I'm going to be contrary here, but this:

and I talked to my friend, and she said that I could see her sister,

stands out to me. You talked to your friend. She said she was okay with you seeing her sister. Exactly what did she think that might mean?

Personally I think that you're fine. Friend has made it clear she doesn't want that kind of relationship with you, and she's said she's okay with you seeing her sister.

Regardless of whether you're technically on the up and up, it seems your friend has changed her mind about being okay with it, and it's up to you to decide what you value more -- as others have said.
posted by aclevername at 8:09 PM on November 5, 2009

My friend and her sister also have this weirdly competitive relationship, they're not super close.
And you're still thinking of doing it because she's smoking hot? You feel slimy for a reason. This is not healthy for anyone involved. If you have a shred of compassion for either of these women in your life, get the hell out of the picture.
posted by june made him a gemini at 8:12 PM on November 5, 2009 [10 favorites]

You know the horrendous saying "bros before hoes" (and its counterpart, "chicks before dicks")? It was invented for situations like yours. You do not place casual sex above your friendships. You don't leave your buddy stranded in a bar so you can go home with the cocktail waitress; you don't stand up your friends because some random chick called you; and you do not, not, not shag your best friend's sister.
posted by DarlingBri at 8:39 PM on November 5, 2009 [1 favorite]

I would also be so so so so so freaked out if an ex fling of mine started hooking up with my sister, either because of jealousy (which is rarely rational) or because I knew the guy wasn't good enough for her. Maybe she's trying to protect her sister.
posted by oinopaponton at 8:46 PM on November 5, 2009 [3 favorites]

[b]If you have a shred of compassion for either of these women in your life, get the hell out of the picture.[/b]

What the hell? The sister wants to date him, may be legitimately interested in him long-term, and he's supposed to stop seeing her out of "compassion" for her? Sorry, she's an adult and gets to make her own decisions. That said, it sounds like you think of the first girl as not so much a 'friend' (certainly not a 'best friend') as 'someone who you like spending time with and might get to sleep with someday'. So I'm not surprised you feel slimy. You should at least try to talk to her about it. Maybe she was OK with you and her sister going on a few dates but is less comfortable now that something's developing out of it - I probably wouldn't want to be looking at a potential brother-in-law who I'd been in a relationship with before either.
posted by Lady Li at 8:47 PM on November 5, 2009

this thread is crazy. she told you she wasn't interested in you, which she's probably not. she continues to fool around with you because she knows you're into her and even though she's not really emotionally invested, she likes that attention and will feed it by making out with you once in a while. and she gave you permission to see her sister. see the sister!

sisterdrama is (1) not your problem, (2) would exist with or with you, and (3) so isn't your problem.

and girl #1 is messing with your head for kicks, that jumps out from your post.
posted by anthropomorphic at 9:16 PM on November 5, 2009 [7 favorites]

Based on what you have written so far, I don't see any reason why you should stop seeing the sister.
posted by Silvertree at 9:17 PM on November 5, 2009

I don't think you have any serious ethical obligations here, other than those you'd have in any relationship (is that what you're asking about?). You should continue to sleep with the sister if it's working out, if it's fun, if it feels to you worth it and she likes it too.
posted by grobstein at 9:32 PM on November 5, 2009

This situation has probably triggered a set of feelings that are only partly about you. Sisters may love each other to bits but can still be competitive and angsty. Real or imagined 'pillow talk' for one, is enough to create conflict, trust issues and jealousy.

Our relationships with our family members are complex enough. Leave your colleague and her sister alone.
posted by honey-barbara at 9:32 PM on November 5, 2009

I think you should figure out why you feel slimy.
posted by salvia at 10:03 PM on November 5, 2009 [1 favorite]

"rodgerd" and "anthropomorphic" are right on. This girl introduced you to her sister ( with her and booze mixed in no less), told you it was fine to see her, then freaks out that your seeing her? Whats that all about? It sounds as though the first girl has a problem. Perhaps with you seeing another other girl ( any), especially her sister.

I think this is sibling jealousy at its worst.

See her if you want to, but there will definitely be some ice between the sisters.
posted by Taurid at 10:41 PM on November 5, 2009

Let's see. If you'd never met the sister, your relationship with your best-friend would still be messed-up, and it sounds like the relationship between the sisters would also still be messed-up. But you did meet the sister, and got on great, which has revealed new facets of what's not right about your relationship with your "best friend."

At this point it seems like you are unlikely to have a decent relationship with your best friend unless you have a come-to-jesus with her and manage to put your relationship on a good footing. I have no idea what will come of your relationship with the sister. Where do you see it going, besides back to bed? Even if it leads to marriage and living happily ever after, it's probably going to feed the existing drama. Is it worth it?
posted by Good Brain at 11:00 PM on November 5, 2009

I keep thinking the most relevant factor is that your friend basically passed on you; to the degree that the two of you are friends, rather than lovers, I don't see what the problem is.
posted by darth_tedious at 11:44 PM on November 5, 2009

for those that "don't see the problem" - did you notice that he still makes out with coworker/"best"friend/exlover? and "makes out" can mean anything from a slight peck, to fucking on the couch - and then he started banging her sister.

when i told my boyfriend about this question and i got to the part where the coworker said "it's ok" he said "that's because she wanted to see if he was really that shitty of a person".

yes, coworker is messing with your head. all the more reason to cut off all nonwork related ties to her, which includes DON'T FUCK HER SISTER.
posted by nadawi at 12:20 AM on November 6, 2009

I'm not quite sure why you keep calling sister #1 your friend. I think that bridge has been burnt.
posted by benzenedream at 1:32 AM on November 6, 2009 [1 favorite]

For better or for worse siblings don't get to choose who their other siblings date.-although they would like to.

I would only follow through with this if it is something more than a 'lark' for you. I put friendship one level below love. A real friendship should be worth more than a roll in the hay.
posted by psycho-alchemy at 1:38 AM on November 6, 2009

There are two rules in life

You're gonna have to cite from the Big Rule Book of Life here. I'd do it for you but I've mislaid my copy.
posted by fire&wings at 3:30 AM on November 6, 2009 [1 favorite]

Someone who doesn't even want a relationship with you doesn't get the privilege of telling you (or their own sibling) who you can and can't date. Do as thou wilt.

Various people are going to flip out to various degrees, yes. But if the only person who disapproves is someone who isn't your boss, mom, wife, or girlfriend, well, feel free to note their disapproval and carry on.
posted by majick at 4:05 AM on November 6, 2009 [1 favorite]

I'm very interested in the sister, and I think, my friend should be OK with it, because she DOESN'T want that kind of relationship with me.

Yes, you should see the sister. Tell the friend if she's really your friend she would be more understanding of the situation.
posted by the_ancient_mariner at 5:37 AM on November 6, 2009

My friend and her sister also have this weirdly competitive relationship, they're not super close.

I know I met her sister through her, but our (me and the sister) relationship really took off. She fantastic, beautiful, funny, smart, and she WANTS to be with me.

Read what you just wrote. Maybe she wants to be with you to spite her sister.

Cool it with both women. You don't want to wade into that shit. Find some other smoking hot, fantastic, beautiful, funny, smart woman who sincerely wants you and isn't trying to one-up her estranged sibling.
posted by LuckySeven~ at 6:16 AM on November 6, 2009 [2 favorites]

for those that "don't see the problem" - did you notice that he still makes out with coworker/"best"friend/exlover? and "makes out" can mean anything from a slight peck, to fucking on the couch - and then he started banging her sister

We can't notice something that isn't there. He never said that he still "makes out" with the coworker. He said they used to occasionally kiss when they were drunk. Unless you think he's a liar, there's no way in hell that his wording means they were fucking on couches. No way. At all.

Furthermore, when he said that he wanted to see the sister, they stopped occasionally kissing when drunk. He's not STILL doing that.

To answer the AskMe: I've always thought that "Don't date a friend's sister" was right up there with "Don't date a friend's ex": some people believe it's a rule and others don't, but there doesn't seem to be any good reason for the rule if all the people involved are decent human beings who aren't players or psychos.

Having said that, this seems like it may be more hassle than it's worth. It'd be one thing if you could compartmentalize the relationship with the sister from the relationship with the best friend. But if she lives in another state, and only visits a couple times a year, and if you actually might want more than just a sex thing, it seems like when the Sister comes to visit, there's going to be situations where you and Sister and BestFriendCoworker are all going to have to hang out, and that shit is going to be uncomfortable.

I think your choices are 1) see the sister in secret (which if they're as competitive as you say is TOTALLY not going to happen), 2) tell the BestFriendCoworker that you understand she's upset and try and work on making her less upset about you having a relationship with her sister, 3) keep seeing the sister when she comes to town without trying to make the BestFriendCoworker happy about it (which may lead to not being friends with BestFriendCoworker anymore), 4) tell the Sister that it's not worth the drama. I think you should try for #2.
posted by 23skidoo at 6:45 AM on November 6, 2009

Don't listen to all these people man, go for it. You say she's just a friend, and she wasn't interested. You can date whoever you want. True love knows no bounds!
posted by OuttaHere at 6:58 AM on November 6, 2009 [1 favorite]

Your friend is Jealous, so dont mind her, if you want to see her go for it......Even if you lose your soo called friend I dont think you need someone who is so "wishy washy" in your life....
posted by The1andonly at 7:25 AM on November 6, 2009

I know I met her sister through her, but our (me and the sister) relationship really took off. She fantastic, beautiful, funny, smart, and she WANTS to be with me.

At this point, I think we're both at loggerheads, I will continue to see her sister (her sister comes up several times a year), and either she comes to grips with this or not. My friend has told me that her and her sister's relationship is fine, it's just me that she has a problem with.

I don't know what exactly I'm looking for with this question, validation maybe? I generally think of myself as a nice guy, but this kind of has me feeling slimy.

It doesn't matter that they're smoking hot. Sorry, it doesn't.

The only way you should continue perusing this is if you can see a real future with the sister--dating, a meaningful relationship. I don't get that sense at all form your post or follow-up. I get the sense that you're enjoying fucking one smoking hot girl while another wrings her hands about it. I imagine that that makes you feel really good and wanted, but it's a shitty thing to do to someone you hooked up with.

Unless you could see, I don't know, marrying the sister. Unless there is real potential there. In which case, all of those "bros before hoes" type rules fly right out the window. But I really don't get the feeling that that's the case, and instead suspect that you're being pretty slimy.
posted by PhoBWanKenobi at 7:39 AM on November 6, 2009 [4 favorites]

This is pretty borderline in my book.

On the one hand, she dumped you. So I think she has even less say about who date.

On the other hand, it's her sister.

And you have no long term potential with the sister. You basically really upset your friend over some casual sex, not over what could be a real relationship.

She also made it known that she didn't want you sleeping with the sister.

Now if it was just a friend and not her sister. I think I would be siding with you, but I think people are allowed to make sort of ridiculous rules about their family members. And this is just about a fling. I actually think the sister is at a lot more fault than you are, but yeah friends don't put friendships at risk over a little casual sex. This is a helluva lot of drama so you could have a fling. I have to believe that on some level (whether you can recognize it or not) you're getting revenge on your friend for dumping you.

And I'll give it to you, as revenge goes, sleeping with her sister is about as good as it gets...
posted by whoaali at 9:12 AM on November 6, 2009

I don’t think this has much, if anything, to do with the sister. I think the heart of the problem is that you have a lot of unresolved feelings for your “best friend”.

I've had a crush on my friend for over a year, so it was very difficult for me when she said she didn't want that kind of relationship with me. I didn't and still don't know how to transition to the type of relationship she wants me with. I thought...that this would make it ok for me to just be friends with her

So, the sister is your rebound girl. Maybe you didn’t plan it, but you essentially used her to help yourself feel better about being rejected by your friend. And as whoali mentioned, it also helped you exact a little “revenge” on your friend. I’m sorry this sounds harsh, but that’s really how it looks. Rebound relationships are generally bound to crash and burn anyway; you’ve added tons of extra drama because of the sister angle. I don’t think you should see the sister anymore. I think you should work on getting over your friend in a way that doesn’t involve further drama.

By the way, she’s not your friend and really never was. You always saw her as someone you wanted to date.
posted by yawper at 9:55 AM on November 6, 2009 [1 favorite]

You don't want drama at work. Decide if this relationship is worth finding another job.
posted by notned at 10:07 AM on November 6, 2009

Here's the thing.

You can date the sister, or be friends with the friend. You can't have both.

And the thing is that the sister is probably only going for you because she knows it's going to bug her sister to death. So enjoy being a prop in their interpersonal drama until she gets tired of it.
posted by Sidhedevil at 10:26 AM on November 6, 2009 [1 favorite]

Here's a little anecdote that I hope will help you.

Many years ago, before my father became my father, he was a single dude with your standard single dude set of priorities. One summer on vacation, he met a couple of sisters who were likewise on vacation. Although he has spared me the details, the implication that he has given me is that he hooked up with one of them.

Upon returning home, he began writing to this girl, and was pleased to find her interested in writing back. Their letters and (less frequently, because it was long distance) phone calls became a regular and treasured part of their lives. It wasn't until several months had passed and they'd become quite smitten with one another that she sent him a picture of herself with one of letters that he realized that he'd been in communication with the other sister. He'd been in contact with the wrong woman, and now he was totally into her. Needless to say, it was kind of awkward.

Well, that "wrong" woman married him, and she became my mother, and the two of them have been very happy together for 30+ years now. And that first sister (my aunt)? She got over it. Way over it. She thinks it's funny. Why? Because she's a grown-up, and that's what adults do. They realize that sometimes the happiness of others is more important than maintaining control of a guy with whom they weren't interested in having a relationship in the first place.

If what you've written here is accurate (and I know from personal experience that RelationshipFilter posters seldom give full and accurate information), then you've done nothing wrong. You presented this woman with a chance for a relationship with you, and she declined it. You discussed seeing her sister, and she gave you permission. It seems clear to me that she's having a stronger reaction now that it's happening than she'd anticipated. This is not uncommon, and there's nothing wrong with it, but that shouldn't dictate your behavior. A few years ago a friend of mine became (what I considered at the time to be) overly familiar with my extremely recent ex-girlfriend. I cut off contact with both of them, which sucked, but then I got over it because it frankly wasn't any of my business who my ex was dating. Now I'm friends with both of them again.

Your friend has every right to be upset and angry and not to talk to you. You have every right to continue seeing her sister. I suspect that your friend will probably need some time away from the both of you, and then she'll eventually get over it. If she can't do that, then she's probably not the right sort of person to be either your lover or your friend.
posted by Parasite Unseen at 10:37 AM on November 6, 2009 [6 favorites]

You know, fuck her, she made her decision, it's her problem. Sleep with the sister, have a good time, and be open an up front about it. Other people's drama is their problem.

(I am assuming I have all the info and everything is legal *ahem*) I also realized I just nthed what Parasite Unseen just said.
posted by Xoebe at 11:17 AM on November 6, 2009 [1 favorite]

But we'd exchanged phone numbers, and I talked to my friend, and she said that I could see her sister, but that any of the tomfoolery that we had been doing (I'm assuming the occasional kissing) would have to stop, which I was fine with.

Your friend (who you kiss when drinking) said she was ok with you hanging out with her sister but asked you not to kiss her. You acted like you were ok with this but then proceed to do the nasty with her sister and think she's totally in the wrong for being mad. You want to keep having sex with your friend's sister knowing that it bothers her but she should take the high road and be fine with you and her competitive sister (who might be doing you to score points against your friend ) being FWB. This is not going to happen.

You'd be on a lot firmer ground if you'd said something about this not being fair/rational before having sex with the sister. Acting like you were ok with a platonic friendship with the sister and then having sex with her is where you crossed a line for me.

Do you have a brother/male cousin/etc? you have a competitive relationship with. How would you feel if she started seeing one for sex? Someone who comes to visit you but then goes over to have sex with your friend (the one you've drunkenly made out with). It would probably be pretty uncomfortable for you. It's probably pretty uncomfortable for your friend. She can't easily end her relationship with her sister but she can end her relationship with you which sounds exactly like what's she's doing.
posted by stray thoughts at 5:20 PM on November 6, 2009

But we'd exchanged phone numbers, and I talked to my friend, and she said that I could see her sister, but that any of the tomfoolery that we had been doing (I'm assuming the occasional kissing) would have to stop, which I was fine with.

Your friend (who you kiss when drinking) said she was ok with you hanging out with her sister but asked you not to kiss her.

I think you're misreading the OP. The BestFriendCoworker said that any occasional kissing between HERSELF and Anon would have to stop.
posted by 23skidoo at 6:37 AM on November 7, 2009

In that case, I apologize to Anon. I thought he meant the occasional kissing that he and the sister did the first night they all went out drinking. If he asked his friend if she was ok with it and got the green light, then I think he's ethically alright .
I'd also say pass because the odds are high for tons of drama you don't want in your work place and would it be worth it for someone you're only planning to see whenever she comes to town. I'd still be wonder if the sister is trying to score against the friend. That's not something that's good to be in the middle of.
posted by stray thoughts at 10:43 PM on November 7, 2009

Ok, not that anyone is reading anymore, this situation has come to a conclusion, well, as least a direction.

I've never felt lower in my life than how I felt after I slept with my friend's sister.
I severely underestimated how much I'd enjoyed our friendship.
How much of dirtbag I felt like.

I didn't want to feel that way, and I don't think of myself as that type of person.

So I wrote my friend an apology letter.

And we talked (and cried) the next day.
She asked me not to see her sister anymore (The sister and I had plans to see each other).

And I agreed, I'd missed her being my friend so much more than I would have thought.
I took her for granted because she wasn't offering what I wanted.

Nothing is fixed or repaired, but maybe it's starting to mend a little.
I can't stand to see my friend hurt.

She is my friend and I have to respect that.
posted by aloysius at 12:52 PM on November 10, 2009 [3 favorites]

That was brave. Good luck to you both.
posted by LuckySeven~ at 12:36 PM on November 11, 2009

Some of us are still reading this. Try and not be too hard on yourself. Your friend as well. A lot of our answers might have had something to do with your actions. Mine included. Thats the danger of answering questions like yours on a site like this. While we may think we have all the facts for the situation in question, we don't always do.
posted by Taurid at 11:53 PM on November 11, 2009