How to preserve my friendship with an ex now that I'm involved with a new person?

June 12, 2012 11:30 AM

We dated for quite a while, but it didn't work out and we've ended up as good friends. But now I'm entering a serious relationship for the first time since it ended, and the shift in my attention seems to be rattling her. How can I handle this gracefully?

Sorry, this is going to be long. But because I'm submitting anonymously and can't clarify things later, I'm trying to be complete up front.

I was emerging from the shadow of a painful divorce when I met A(nn). It was far enough behind me that I felt past the rebound stage and ready for a real relationship, but I hadn't been in one yet. We started dating and I liked Ann. I enjoyed her company, we shared interests, we had a good time together, and we were affectionate and supportive of each other. But my feelings never developed into real love. Nonetheless, we dated for almost a year.

I stayed that long because I wasn't sure I trusted that lack of stronger feeling given what I'd been through. I liked her. She was good to me and I needed that in my life. And I thought my feelings might grow if I was patient with my rebooting heart. Eventually I realized that it wasn't happening. I also knew her feelings for me were stronger, and I wasn't doing her any favors by letting her get more deeply involved when I knew it wasn't going further. So I broke up with her, saying that I thought we had a really good friendship and we should keep that even if that was all it was. This would be a little over a year ago.

And we have become really good friends since then. We talk often, do things together, grab dinner, and so on. It does sound kind of like dating, actually, but has stayed purely platonic. I'd estimate we see each other two, maybe three times a month. I value her friendship for myself, but I think part of it for me is also guilt about effectively stringing her along for a year. She's also in a sort of chronic career/financial crisis, perpetually a couple months from finally finishing a doctoral thesis that's always stressing her out, has faced family medical crises, and lives in a city where she doesn't really have that much of a support network. Basically, she needs a good friend and I want to be there for her. It's not like I can't use a good friend too.

About six months after we broke up, I dipped my toe in the dating pool again. What's followed has been a lot of first dates, and a few subsequent ones, but nothing's gotten serious. Ann is aware of this, and has been quite supportive, even taking it upon herself to overhaul my wardrobe. She herself has not been dating, though she keeps saying she's going to as soon as the thesis is done, and occasionally mentions that some guy flirted with her.

So that was the status quo, until B(eth) came along. Beth and I have been seeing each other for about a month now. Other people I was in that first date stage with sort of faded away and I haven't looked for others. It's still a new thing and I don't know where it will go, but I've hidden my online profile and we've started talking exclusivity. Basically, this looks like my first real relationship since Ann.

Ann's been generally aware of this dating ebb and flow, mainly in a "what'd you do this weekend?" "went to a show," "oh, with X?" "yeah," kind of way. I don't specifically inform her of my dating schedule. But as she's noticed that X increasingly equals Beth, she seems to be a bit rattled. She's mentioned a couple times that what I ought to be doing is keeping three dating partners in rotation. I ignored that, but then came something that was harder to ignore.

Ann called to ask if I was free for an outing on Saturday. I wouldn't mind doing something with her, but I wanted to check with Beth first and see what our weekend plans were, so my answer was that I didn't know yet. She asked if I actually had something on the calendar and I admitted I didn't. She was definitely put out by this. Her response was along the lines of "so some temporary woman is more important than me." Where we left it was that I'd get back to her within a day and let her know. But the exchange has me worried.

I'm getting the sense that Ann still has proprietary feelings toward me. She could play along with me dating other people as long as it was casual, and didn't threaten her share of my attention. But now that Beth has come along, with whom my goal is to not be "temporary," she's having issues. I'm moving into a place where I feel Beth has first claim on my time now, and that hasn't happened before.

I don't want to hurt Ann, and I do value her friendship and want to maintain it. But part of me worries that, by sticking around and being such a close friend, by effectively maintaining pretty much everything about our relationship except the romantic and physical parts, I've sort of enabled her to never quite completely break it off with me.

So my basic question is how do I handle this transition with some modicum of grace? And I guess the deeper one is, by trying to be a good friend to Ann, am I actually keeping her from moving on and ultimately hurting her more than I'm helping?

posted by anonymous to human relations (39 answers total)

Ask mefi are strong proponents of severing ties when breaking up with someone who might still have feelings for you. You didn't do that, and it sounds like it was a fine decision for both of you at the time, but it means some of the mourning the relationship has been bumped out to now.

The best way to be gracious would be to treat Ann gently - if she says something about Beth being temporary, you could say that things are getting serious, yes, but you still value her friendship. Ask if she can do something another time. You can't change how she feels, but you can be kind and honest - and it sounds like you're well on the way, so good luck!
posted by ldthomps at 11:42 AM on June 12, 2012 [1 favorite]

To paraphrase Radiohead, Ann doesn't want to be your friend-- she wants to be your lover. She is acting like this because as long as you were single you could be her pseudoboyfriend (and she was probably hoping she could win you back.)

If you want to be with Beth, be with Beth and make it very explicitly clear to Ann that she needs to respect your relationship with her (B) or that you cannot be friends. When you say, "I do value her friendship and want to maintain it," you have it a little backwards; Ann needs to be the one to want maintain your friendship right now, if you are truly friends. Friends don't refer to (potential) significant others as "temporary women" unless they are jealous.

Oh, and for god's sake, please be honest with Beth because there is nothing worse than feeling like the other woman in your own relationship.
posted by Flamingo at 11:43 AM on June 12, 2012 [8 favorites]

Transition by being honest with Ann when necessary (don't call just to say you have a date with Beth), and maybe cutting down on the dinners and other date-like events.

To your deeper question, yes, most likely. Your worry that your relationship is continuing is spot on; there was no real break-up. This platonic dating has taken priority over your non-platonic relationships, giving her the hope that you might add romance/physicality into the mix at some point in the future. She needs to develop a support network in her city outside of you, her non-partner partner.
posted by RainyJay at 11:45 AM on June 12, 2012

I recently got broken up with, and the person who did the breaking up is somebody whom I value and want to keep as a friend going forwards. Nevertheless, I am taking a three month break from all communication with her simply so that I can let go of my romantic feelings completely.

Obviously this approach is challenging - it requires people to prioritize the rational analysis of their head over what their heart wants. Nevertheless, it's the best thing in the long run. You may not have implemented that process when you broke up with Ann but it's not too late to do so now. (Although I recommend explaining your intent to her so that she doesn't feel that your sudden lack of contact is a breach of friendship.)
posted by wolfdreams01 at 11:47 AM on June 12, 2012

The only person who could answer this question is Ann. The best thing to do would be to ask her if she's all right with all this, etc. So that's what you should do.

But if I were called upon to speculate, I would say this: Ann is basically over you and over your relationship, but at the same time, she hasn't previously had to deal with the sense of finality that she is now coming up against. There are stages of ending a relationship, and she has been more or less okay with the previous ones, but now comes one of the last stages when the door is well and truly closed - even if she never actually wanted to go through that door again - and it's bugging her. She might not even really understand why, or be able to put it in terms so concrete, so if you ask her why she's being like this, she might not know for certain.

This happens. I've felt antipathy towards the new significant others of exes of mine that I would never actually want to date again. Call it jealousy if you like, and you might even be right, but jealousy doesn't mean she wants you back. Doesn't mean she doesn't, either.

But the only way to know - and the smart thing to do here - is just to figure out a no-stress, no-pressure way to ask her.
posted by FAMOUS MONSTER at 11:49 AM on June 12, 2012 [3 favorites]

But now that Beth has come along, with whom my goal is to not be "temporary,"

This is the message that you need to politely get across to A. My script would be "Ann, you are a good friend of mine and I value our friendship considerably. However my plan has always been for us to be friends and for me to find someone who I could date and have it be a long-term thing. This seems to be a little difficult for you, but I need us to be friends which means I need you to be supportive of my deepening relationship here or I need us to spend less time together."

No apologies, no "you're being weird" just some explanation. Then I'd ask if she has questions and I'd move forward trying to do the right thing [i.e. fewer datelike interactions with Ann, full explanation to Beth who may or may not sense some odd friction there] and let Ann decide what she'd like moving forward. it may be a temporary adjustment or it may be that she's not really up for being your single friend as you move closer to being part of a couple.

But one thing needs to be clear, and you seem to be clear on it, you don't have extended "But what about our relationship?" conversations with Ann. She is not your significant other even if she is a significant friend. She will have to find her own comfortable place with your changing relationship just as you do. It's not your job to shepherd her through this. I'd let yourself off the hook for the year of dating that didn't turn into anything. It's really a no-harm-no-foul situation and should not be parlayed into any increased responsibility at this point.
posted by jessamyn at 11:53 AM on June 12, 2012 [14 favorites]

Yeah, you're telling the story, but it sounds to me like you're spot-on in your analysis. Good friends don't refer to their good friends' significant (moving-towards-serious) others as "some temporary woman."

It's really hard to say if your continuing friendship is holding her back from moving on, or if you're hurting her by continuing to be friends. I kind of think that needs to be her call, unless she makes you so uncomfortable that you need to stop being friends for your own sake. If the friendship turns bad for you, of course, you should walk away, and not stay out of some obligation of guilt.

If she makes a comment like that, I would be direct and say something like: "Things are going well and my intent is not for this to be temporary. Of course our friendship is important to me, but my relationship with Beth is important to me, too." Challenge Ann if she talks shit about your woman, but don't rub her nose in it, essentially.

There's a pretty decent chance that your increasingly serious relationship with Beth will be the same kind of shock to Ann's system that cutting off contact would have been, so at this point the issue of cutting ties might be moot.
posted by J. Wilson at 11:56 AM on June 12, 2012 [1 favorite]

I actually have been Ann with three different guys. Based on that experience, and on the three different ways that those three guys handled it:

1. Maintaining a platonic relationship with her, provided it's something you wanted to do anyway, is not keeping her from moving on. That is, if she's using it as an excuse to keep from moving on, that is entirely on her, and not any fault of yours.

2. The fact that you kept it platonic is a good thing, as well as the fact that you were open about your dating. You didn't try to keep anything from her, and she was going into it with eyes open. Thus any kind of "residual feelings" she might have for you are entirely coming from her as opposed to you having lead her on.

3. Yes, there is the possibility Ann may have some type of feelings for you. But it isn't necessarily as simple as "she still is in love with you" kind of feelings. She may have accepted that you are now platonic friends, but still likes being the center of your attention. That kind of giving-up-of attention can be a bit difficult to process. But -- again, nothing you have done has exacerbated that.

I would have a conversation with Ann about all of this -- giving her the heads-up that Beth is kind of turning into something you want to pursue a bit more seriously. It doesn't have to mean that you'll never see Ann again, but - that does depend on Ann, and make sure she knows that. You want to keep Ann as a friend, and you do want to keep doing things with her, but Ann has to respect that Beth is now a priority for you. And right now, you're concerned Ann is having some trouble with that, and how can you both work through that? This is pretty close to what the guy who handled our post-breakup transition best did - he was honest and up-front about how New Girl was important, but he still did things with me; he was patient with me occasionally acting a little weird, and accepted my setting a boundary early on of "okay, look, I accept that you're happy with her, but you just broke up with ME two months ago so I'd really rather you not gush about how awesome she is QUITE so much right now". But he in turn set some boundaries of "okay, that's fair, but then YOU have to please not call me at 11 at night when there's a chance she might be over becuase, um, awkward."

Things were only kind of tense for a couple months, but then they sorted themselves out after that, and that was all ten years ago and he's still with that girl and I recently apologized for not being able to listen to him gush about her (he said "what? Oh, that, yeah, no, I totally understood and it's cool"). Be honest with her, like you have been; be patient with her, because she may be processing some weird stuff; but be firm about your own boundaries. It is possible. Good luck.
posted by EmpressCallipygos at 11:56 AM on June 12, 2012 [3 favorites]

Are you being a good friend to her, though? You didn't have plans for Saturday and you told Ann, in effect, that she is secondary to plans you didn't have yet with Beth. That doesn't make me feel valued as a friend, romantic backstory or not.

She was out of line with her response, though, so I'd sit down and have a talk with her to see where her head is at. I'd apologize for what you did and tell her that you were hurt by her response. That Beth is someone who means something to you right now and you'd hope she'd be happy for you as you'd be if she found someone.
posted by inturnaround at 11:56 AM on June 12, 2012 [7 favorites]

Ann has spent the months since you broke up hoping that if she just gives you the space you need, you'll eventually come back to her. That's not to say that her friendship isn't genuine; I'm sure it is. But she's been hoping for more, consciously or subconsciously, and Beth's arrival is her first real proof that it's not going to happen.

Be prepared for her to behave like you're breaking up with her all over again, because in her mind, you are. Be prepared for her to feel like she played every role you asked her to play--girlfriend, supportive best friend, confidant, wingman--cheerfully, and now she's getting the shaft when she should be getting the happy ending. Be prepared for her to feel like she did everything right, and now she's left in the dust as you use the dating and friendship skills you developed with her on someone else. It won't seem fair to her, and it might never seem fair.

All you can do is treat Ann like you'd treat any other friend-you've-never-dated. Do you have any other purely platonic friends whose place in your life is non-negotiable no matter who you're dating at the time? Ann can be that person. You can dedicate time to her (a standing Thursday night dinner? Monday drinks? A weekly phone call if in-person time isn't possible?) that it sacrosanct and is always you-and-Ann time that Beth never gets to upend or interrupt, while still giving Beth the rest of your attention. If you value Ann's friendship, make a point of keeping that commitment of time to her, being very consistent, as proof that her presence in your life isn't disposable when a new girl comes along.

I know it's hard when you're in the limerance stage and can't imagine committing time to anyone else because what if Beth wants to hang out that night and will she still like you if you say you're busy, etc. But if you truly value Ann's friendship and want her to feel welcome in your life despite your new relationship, you must commit consistent time and space in your life to Ann and only Ann.
posted by jesourie at 11:57 AM on June 12, 2012 [5 favorites]

Oh, and a p.s. from me about my own friend and his "Beth" of ten years -- I even love Beth now too. He's visibly crazy for her, and I'm happy for him.
posted by EmpressCallipygos at 12:02 PM on June 12, 2012

The good news is that you may be overreading this a little bit. I get the concern, but maybe, a little, you may be overreading it because you feel guilty and you've always secretly kind of assumed she's still into you.

As much as you have every right in the world to prioritize your relationship with Beth, when Ann is saying, "Hey, can we do something Saturday?" and you're saying, basically, "I have to ask Beth," that's not necessarily a great feeling whether she still "wants more" or not, because ... it's not like Ann is asking for your whole weekend. If you don't have any plans, she might reasonably wonder why you can't make plans for one day when you could always, you know, see Beth the rest of the time.

I'm not saying your intuition isn't right, but as much as friends have to be respectful of new relationships, somebody you started dating a month ago should, I think, be okay with you saying, "I actually have plans with a friend on Saturday; how about Sunday?" You're not doing anything wrong, but there's a certain "I am putting you on hold not for other plans but for the opportunity to potentially MAKE other plans" feeling that she is probably getting that might or might not have anything to do with the fact that you dated. I mean, as the friend, this really does feel like "I guess we could hang out if I don't wind up getting a better offer," and that doesn't require romantic complications to feel unpleasant.
posted by Linda_Holmes at 12:04 PM on June 12, 2012 [12 favorites]

Her response was along the lines of "so some temporary woman is more important than me."

What did you say when she said that? Because that was fucking bizarre. It wasn't like you were breaking plans with her to go on a date*--you were hoping a date would materialize, so you were hesitant to make plans with a friend. She is not getting that she is your friend and that, like every other friend in your life, sometimes you are going to pass on a chance for friend-socializing in order to go on a date.

If she doesn't get that, perhaps she's not doing well with being your friend. I agree that it sounds like she's "hovering" and waiting for you two to get back together, but I also think that being cordially honest with her could put the friendship back on a tenable track.

*which is almost never OK with friends of any gender, except in some totally exceptional circumstance like "She's leaving Tuesday for six months in the space station, and this is the only time we can see each other!"
posted by Sidhedevil at 12:05 PM on June 12, 2012 [1 favorite]

Mr. Sidhedevil has a former girlfriend who is a dear friend of both of us now who did a bit of this after their breakup. (He was not clear enough about his boundaries, which was a huge piece of the problem, something that it sounds like you're doing very mindfully.) He and she worked it out, and we have all been delightful friends ever since. Seconding EmpressCallipygos that this is a situation that can be resolved if everyone is honest and candid.
posted by Sidhedevil at 12:08 PM on June 12, 2012

You are spot on when you say:
But part of me worries that, by sticking around and being such a close friend, by effectively maintaining pretty much everything about our relationship except the romantic and physical parts, I've sort of enabled her to never quite completely break it off with me.

She doesn't want to be friends she wants to get back together.
Have a come to Jesus meeting with her. It's up to her to maintain the relationship if she wants to with Beth now in the picture. You've been clear to her that you DO want to remain friends.
Oh, and the call for Saturday night plans was her big test to see how serious you really are with Beth. Most of us don't get put out if a truly platonic friend may have other plans for Saturday night.
posted by Snazzy67 at 12:08 PM on June 12, 2012

Her?

To be serious, I think you should just do what you'd like with this new woman, and if Ann has a real problem she'll clearly let you know. Her remark might just be her semi-serious way of dealing with something she's already accepted, namely that you are looking for a romantic relationship with someone. It might also be a sign that she's totally into you and wants you for herself, but it's hard to tell from that one data point.

You can't always avoid hurting people, because we tend to pin our hopes on the future actions of others without their knowledge sometimes. You're not responsible for living up to a script she has in her head. It sounds like you've been more than fair and open about what you want.
posted by clockzero at 12:14 PM on June 12, 2012

Upon closer review:

Oh, and the call for Saturday night plans was her big test to see how serious you really are with Beth. Most of us don't get put out if a truly platonic friend may have other plans for Saturday night.

Yeah, but I think most of us would get a little miffed if a platonic friend said "I don't know if I want to do anything with you yet because I may make plans with so-and-so, I just haven't decided yet." No one likes to know quite so nakedly that they're a plan "b".

This is what the white lie of "I may have tentative plans, let me double-check and get back to you" is for.
posted by EmpressCallipygos at 12:18 PM on June 12, 2012 [16 favorites]

Exactly -- and if you're in the phase of a relationship where the expectation is that you'll be doing something but you haven't nailed down what, it isn't even really that much of a lie.
posted by MCMikeNamara at 12:21 PM on June 12, 2012

if one of my friends told me they didn't have any plans yet with their SO but wouldn't commit to me until they figured out if they did have plans, i'd be kind of pissed too. fortunately, i have friends who do make plans with their friends independently of their SO, first come, first served. so regardless of what her underlying feelings are for you, that was kind of a dick thing to tell her. or at least tell her you'll have to get back to her.
posted by violetk at 12:24 PM on June 12, 2012 [4 favorites]

Yeah, but I think most of us would get a little miffed if a platonic friend said "I don't know if I want to do anything with you yet because I may make plans with so-and-so, I just haven't decided yet."

"Sounds good, but I don't know if I'll be free Saturday; does Friday work for you? Or maybe the following Saturday?" covers a lot of ground. Agree that "I'll have to see if I'm doing something with Beth" is unnecessarily rude.
posted by Sidhedevil at 12:30 PM on June 12, 2012 [4 favorites]

In other words, if you started off by saying "I don't know if I'm free that night" and Ann kept pushing you on it, she was the one who was being rude. It's not like people get to call "dibs" on each other's schedules.
posted by Sidhedevil at 12:32 PM on June 12, 2012

You didn't mention whether Ann and Beth have met yet. If not, maybe it's time to orchestrate a group gathering that can include them both, perhaps with some other friends. Without any firsthand experience of Beth, Ann's imagination is free to run wild and prey on any shred of regret still floating around in her brain.

But once they meet, Beth becomes a real person to Ann and hopefully someone she likes. In a similar vein, there's also a possibility that Beth is worrying about Ann's role in your life. Both Ann and Beth can truthfully be told that you're eager to introduce them to each other because they both play important, albeit different, roles in your life. Yes there may be some flouncing of tailfeathers--either with Ann trying to demonstrate her longer history with you to Beth or Beth playing up her intimacy with you to Ann--that could be momentarily uncomfortable, but it's the first step on the road to the sort of long-term friendship EmpressCallipygos described above.

Just watch yourself for any self-serving ego-gratifying things you might be doing to stir the pot with either Ann or Beth, especially if it's "Let's You and She Fight" or some scenario where you're essentially saying "Now Girls, Calm Down." I'm not saying your post suggests this is happening, but it might be just a little bit tempting and so you should police yourself for it.
posted by carmicha at 12:34 PM on June 12, 2012

On further reflection, check it out:

I'm moving into a place where I feel Beth has first claim on my time now, and that hasn't happened before.

I mean, she's being shuffled down the list so Beth can take priority. She knows you're doing this. You know you're doing this. As you can see from the above responses, some people would be bothered by this regardless of whether or not jealousy is in play.

So, like I say, talk to her about it, but don't frame it in terms of whether or not you think this is because Ann still wants to be with you. Frame this as, "What's up?" as opposed to "I think that what's up is that you still have proprietary feelings toward me, am I right or wrong about that?"

This could be nothing, it could be something, it could be jealousy or simple crossed mental wires, but until you've talked to Ann about it, the only thing you or we can offer is speculation.
posted by FAMOUS MONSTER at 12:38 PM on June 12, 2012

I don't think it's rude at all for someone in a couple to say "let me check with Beth to see if we've got something going on." It happens with pretty much every couple I know. "Gotta check with the boss first," the guy will say. Or "Dude's had a long week, let me see if he wants to do something first." The difference is, it sounds like you've gone from dating to exclusive without letting your friend in on the secret.

So you broke it off, but for the most part you've been pretty much exclusive and always available up to now, even when dating other people. You say she's been leaning on you socially, but it sounds like you've been leaning on her socially too. Two single people, being each other's wingman/support. Other comments have praised you for being clear but have you been clear that this one's different? From the exchange you relate, it sounds like you were seriously giving out information on a strictly need-to-know basis.


Ann's been generally aware of this dating ebb and flow, mainly in a "what'd you do this weekend?" "went to a show," "oh, with X?" "yeah," kind of way.

That's pretty passive on your part. She asks, you hedge. She asks again, you admit the truth as though there's something secretive about what you're doing. If Ann is carrying a torch, then I agree that you shouldn't rub a new woman in her face. But if you're truly friends, then what friends do is say "hey, I think I may have met someone with potential" and "I am thinking about this new girl a lot" and straight-up "let me check with Beth to see if we've got something going on before I make plans." Or even, "I'd like you to meet Beth."


She's mentioned a couple times that what I ought to be doing is keeping three dating partners in rotation. I ignored that, but then came something that was harder to ignore.

Why would you ignore something your friend offered by way of dating advice? If it was another friend, wouldn't you have responded with "yeah but this woman is really interesting..." Ann's trying to communicate with you and your refusal to respond is not fair.


Ann called to ask if I was free for an outing on Saturday. I wouldn't mind doing something with her, but I wanted to check with Beth first and see what our weekend plans were, so my answer was that I didn't know yet. She asked if I actually had something on the calendar and I admitted I didn't. ... Where we left it was that I'd get back to her within a day and let her know.

So she asks, you hedge. She asks again, you "admit" the truth. Then you leave her hanging.

I think you are not being fair to Ann.
posted by headnsouth at 12:52 PM on June 12, 2012 [3 favorites]

I've been Ann. It's painful and there is no way you can frame anything that won't have her realizing that she is losing you, even as a readily available platonic friend to hang out with. She's losing you and that's going to be sad for her. There's nothing you can can do about it, really. Go and be with Beth, and Ann will work it out somehow.
posted by ThatCanadianGirl at 12:55 PM on June 12, 2012 [1 favorite]

How to preserve my friendship with an ex now that I'm involved with a new person?

Is this really your question? Because nothing in your post suggests that this is your concern. You don't sound fond of Ann; you're portraying her as a PITA. You sound like you're done with the friendship now that Beth is in the picture. If you do want to preserve your friendship, give her Ann a call and make plans to have coffee. Tell her that you're really into Beth and you hope that it will become serious, but that you really still value your friendship and that you still want to hang out. Problem solved, if this really is the problem.
posted by Wordwoman at 1:36 PM on June 12, 2012 [7 favorites]

Why would you ignore something your friend offered by way of dating advice? If it was another friend, wouldn't you have responded with "yeah but this woman is really interesting..." Ann's trying to communicate with you and your refusal to respond is not fair.


Yeah. I mean, I think it's totally possible that Ann /does/ still have feelings for you, but maybe not. It looks like in some ways, you haven't been ready to let go of your connection with Ann either. You haven't been clear about things getting serious with Beth, and you've only been dating casually before - so it does seem like some "casual date" is getting in the way of your friendship.

If I had a friend who seemed only interested in "bits of fluff", and he started to prioritize one of his "bits of fluff" over our friendship, without telling me "Hey, this one's different," I'd be monstrously insulted. I'd think of it as, "Oh, I see, random casual sex is more important than our friendship."

You may have been concealing this so as not to hurt Ann, but for whatever reason, you've been concealing it and being shady - and this is what Ann is reacting to.

Sit her down and tell her the full score. Don't worry about easing into it.
posted by corb at 1:38 PM on June 12, 2012 [3 favorites]

[Folks maybe stick to answering the OPs questions please? Thank you.]
posted by jessamyn at 2:35 PM on June 12, 2012

There is a hidden, dark truth here, a subtext to all this of which she is probably painfully aware but you've pushed back because it's hard to face.

You used her. Not consciously, or maliciously, but you used her in the way that a lot of us use people without realizing it.

You used her to reboot your heart after your divorce, and then when once your confidence had been recharged by her validation of you, you let her go. I think on some level you kept her way past the point where you knew you weren't in love because having a girlfriend felt good and you were lonely.

It sounds like when you guys met up you were both in bad places, but her giving nature helped you get out of your funk. Unfortunately, her giving without receiving in return has probably left her in a deeper hole than she was before. I'm sure she feels abandoned.

Every time you guys meet up she is reminded of this feeling. It must be torture. If she had any self esteem she would cut contact with you. But she is probably so desperate right now for any kind of connection given how little support she has in her life, that the pain of seeing you date other people seems like a better alternative to being totally alone.

The kindest thing you could do for her would be to stop seeing her at all. But you have to approach this conversation in the right way, so she knows that it's not another rejection of her. Honestly I would tell her that you feel like you kind of used her for the reasons I wrote above, and that you're really sorry for that. And that you feel like the only way you can make things better now is to do what's best for her...which is to stop seeing her. Tell her that it's painful for you and it's not what *you* want but you know it's what would be best for her. Really emphasize this point.
posted by timsneezed at 2:44 PM on June 12, 2012 [3 favorites]

Is this really your question? Because nothing in your post suggests that this is your concern. You don't sound fond of Ann; you're portraying her as a PITA. You sound like you're done with the friendship now that Beth is in the picture. If you do want to preserve your friendship, give her Ann a call and make plans to have coffee. Tell her that you're really into Beth and you hope that it will become serious, but that you really still value your friendship and that you still want to hang out. Problem solved, if this really is the problem.

Right. It's clear you don't even value Ann much as a friend. You're continuing to use her. Before it was as an antidote to loneliness, now it's to assuage your feelings of guilt.
posted by timsneezed at 2:48 PM on June 12, 2012 [1 favorite]

And I guess the deeper one is, by trying to be a good friend to Ann, am I actually keeping her from moving on and ultimately hurting her more than I'm helping?

I think you've hit the nail on the head here. She's very obviously been hoping that your friendship re-evolves into something more romantic and... that hasn't happened.

You can't protect her feelings. If she's jealous of Beth, that's not your problem. There's no reason to be rude or cruel, but a simple straightforward conversation that you lay it out that you're with someone else now and you really find it hard to continue hanging out with her when she's being difficult about it isn't being mean - it's doing the right thing to keep from stringing her along.

There's a concept in Buddhism called "Idiot Compassion" that you might find useful here. The main point is that often, we go so far out of our way to avoid hurting someone else that we're actually hurting them by not letting them experience what's really going on and being able to learn from it. Your heart is in the right place, but you're absolutely right that this isn't doing her any favors.

Best of luck.
posted by sonika at 2:48 PM on June 12, 2012 [4 favorites]

Like timsneezed, I also popped in here to point out that you used Ann as a placeholder, whether you meant to or not. You also make her out to be your "Pity Friend." No one likes that role.

Please just break up with Ann. For good.

She doesn't need your pity, she can't get back the time and attention she wasted on you since you broke up romantically, and the adjustment of shuffling her to the outer reaches of the "friend zone" just means drama for you both at this point.

Next time, don't use your ex-girlfriend like a pseudo-relationship-type bookmark, and you'll avoid creating this type of drama.
posted by jbenben at 3:00 PM on June 12, 2012 [5 favorites]

I wouldn't assume Ann is interested in you. And saying something to Ann in a way that assumes that is 1) egotistical (unless you are confident you are actually that awesome and irresistable) 2) insulting and 3) likely to piss her off and frustrate her. IN regard to 3, the problem is that from there on out, whatever she does will put her in a situation of looking like she does like you. If she protests and gets mad, you will assume she likes you. If she is quiet and doesn't say anything, you will assume she is processing her deep feelings for you. Honestly, it is pretty likely that after this long, she actually doesn't like you and may actually be too busy with her thesis to date. Take a look at what FAMOUS MONSTER said. I think he/she is right.

As for what you should do, I personally think it's kinda crappy that you won't make plans with a friend when you don't have plans because you are hoping you will have plans. Unless you and Beth are committed to always doing something on X day and Ann requests your time on X day, I don't know why you would say you are waiting to see if something better comes along. That's called being a poor friend and she has a right to be upset. I wouldn't have used the term "temporary" if I were her, but it is kind of a rude thing to do to someone that sounds like she has been nothing but a friend to you since you all decided to put an end to the romantic aspect of your relationship.
posted by superfille at 3:15 PM on June 12, 2012

I don't think it's horribly rude to tell a friend, hey, let me get back to you about Saturday tomorrow, I want to check in with my new love interest about Saturday first. I feel like that's pretty common -- people fall off the face of the map when they are in new relationships.

That, combined with her reaction that specifically took a shot at Beth's permanence in your life, says to me that this bothered her more than it would have coming from an ordinary friend. This doesn't mean that she necessarily wants you back (although that is possible), but it says to me that at least, she enjoys being the center your attention and doesn't want to give that up. I don't think there's anything to do -- time will tell whether she can deal with being bumped down below "girlfriend" in your priority list.
posted by J. Wilson at 3:28 PM on June 12, 2012 [2 favorites]

I would remove any concerns about her still having feelings for you. They might exist, but that is on her to resolve, and you trying to tell her about how in love she is with you will not go over well.

But I've had a few times in my life where I was very much in No Dating Territory. And it's easy to start treating a close friend like your Significant Other. And it's hard to sort it out when they start actually dating someone. Or you start dating someone, and suddenly change the boundaries of the relationship without warning.

Ann is used to having your undivided attention every other week. And now you've gone from making time for her to be close friend to fitting her in to the free spaces. It's bruising, even if it's a normal part of being so lovestruck you're hoping Beth wants to spend her Saturday night with you.

Remind her that this is part of dating. Apologize that limerance makes a dick out of most people. But also figure out if you want to be a decent friend and make the time for her. I'll agree it sounds a bit ambivalent about whether or not you want this friendship. It sounds like you think your friendship is a second place trophy you owe her because you didn't want to keep dating her.
posted by politikitty at 3:45 PM on June 12, 2012

I was in the Beth position once. The You was afraid of hurting Ann's feelings and wasn't as direct with her as he could have been. Ann became increasingly controlling, territorial and aggressive. Ultimately, she was extremely rude to me when we finally met, which ruined their friendship and almost ruined our budding relationship.

Do be VERY clear with Ann and set the necessary boundaries. If Ann is unable to accept those boundaries, you can't be friends with her and seek a romantic relationship with Beth or anyone else. It will likely not be easy for Beth (or future Beths) to trust you if you persists in indulging Ann's childish feelings. No one wants to be with someone whose "best friend" thinks that you are a "temporary woman" and that she is the most important relationship. Do not allow Ann to disrespect Beth-- an unsuspecting, innocent party-- like that.
posted by lalalana at 5:32 PM on June 12, 2012 [5 favorites]

Another thing: If Ann does not accept your boundaries, It doesn't matter WHY-- whether she is jealous or just miffed because you are being flaky. She needs to let you set them.
posted by lalalana at 5:41 PM on June 12, 2012

I don't think you did anything wrong with Ann. Relationships are tricky. You were as honest as you could be throughout, including keeping Phase Two platonic. You need to move on now, and let Ann process this new development however she will.
posted by ThatCanadianGirl at 6:43 PM on June 12, 2012

You have a new love interest you want to be serious about and that's wonderful. You're doing the right thing in giving her importance in your life. You say you want to preserve your friendship with Ann. So ask yourself what your friendship is based on with Ann? Do you wish to one day introduce Ann to Beth? How do you see Ann integrating in the rest of your life? Do you just feel obligated to be her friend or has she become part of a support system for you?

I've been "Beth" and knowing that an "Ann" exists still trying to pursue my partner and my partner engaging it and not setting boundaries has caused a lot of heartache. Sometimes being polite can be interpreted as interest by a friend that has feelings for you, so as others have said make it clear to Ann and if she is a good friend she'll root you on. Be kind to your Beth. :)
posted by i_wear_boots at 12:01 PM on June 20, 2012