What a mess!
November 1, 2010 1:18 PM   Subscribe

I recently slept with an old flame. We've decided that we'd like to start dating, but this causes problems with the relationship I'm currently in and the friend who's obsessed with the old flame. Soap opera details inside...

I February of this year I had sex with a girl (Jane) that I'd been interested in. It was passionate, but I was in a place mentally where I didn't want to date anyone (I was depressed and living far away from my friends - the only time I could see anyone was on the weekends). We talked it over and agreed that it was a one time thing.

She was inside of my immediate circle of friends, and so a mutual guy friend (Henry) decided to try to date Jane. They spent some time together, but she decided that they weren't right for one another. She's had multiple conversations with him to call things off, but he's still very interested in her and it's gotten a little bit creepy.

I'd been dating another girl (Sarah) for about two months, but things haven't been clicking for me. She's incredibly dedicated to her job, spends pretty much all of her time with it, except for once or twice (if even that) a week that we can spend together, and even then it's all she talks about. This is no excuse for me cheating, but it does say that I was thinking about calling it off even before this happened.

Jane and I both got a little bit drunk, and I ended up going back to her place with some other friends, at first just to hang out, although at a certain point things began to build up steam and we had sex again. It was great, and we both talked about it the day after, realizing that we'd like to date.

I know what I did was wrong. I should've broken it off with my current relationship first, definitely, and knowing what I know about her and Henry I should've talked to him first. I didn't. Now I have to deal with my mistakes.

1.) I know that the right thing to do is to tell Sarah that I cheated on her, but is this really the kindest thing? Is it adding insult to injury to dump her and reveal that I'd cheated? My sense that I'd gotten from her (perhaps mistakenly) is that she wasn't entirely happy either.

2.) I haven't broken up with someone in a while. All things above considered, what's the best way to do this? Public place? My house?

3.) When I talk to Henry (I'm thinking over lunch in a public place) is it best to also have Jane there, or does that feel like an ambush? If you have any additional questions you can email me at mefiquestion112@yahoo.com

I realize that what I did was wrong. I feel terribly about it, and if I could then I wouldn't have gone back with her. But it's not like she was just some random person - we do have history together, and I think that we should've been dating the entire time. I'm really confused, and not entirely great with relationships. I hope I can figure something out that causes the least amount of harm all around.
posted by anonymous to Human Relations (29 answers total) 2 users marked this as a favorite
3. Do not have Jane there. Have it over coffee or a beer or something where Henry can opt for an easy escape.
posted by spec80 at 1:25 PM on November 1, 2010

I know that the right thing to do is to tell Sarah that I cheated on her, but is this really the kindest thing?

It is neither the right thing nor the nice thing to do. So don't do it. You're on the right track here, so if you're feeling guilty, ditch the "truth is always the answer" morality. It might sound capital-G Good in theory but, practically, it's not going to make things any easier on her, and it'll make you feel guiltier. And you're probably feeling guilty enough.

All things above considered, what's the best way to do this? Public place? My house?

Her place would probably be the best. Once it's over with, she can call some friends over for consolation (or just do whatever it is she does after breakups) immediately and won't have to worry about getting home in a wreck-y state.

When I talk to Henry...

You are not going to try to date Henry, so you do not need to talk to Henry. Jane is as active an agent as you are in all this and this part is Jane's responsibility. If she wants you there for comfort or support, that's fine, but you don't need to take the initiative on this. She's not a product you're exchanging, she's a grown woman who can handle herself or ask for help if she needs it.
posted by griphus at 1:26 PM on November 1, 2010 [21 favorites]

1) The right thing to do is to break things off immediately. If you slept with Sarah after sleeping with Jane, you need to tell her that. Otherwise, I'd argue you don't have to tell her the details. If my girlfriend cheated on me, but genuinely intended to date that person, and hadn't continued seeing me afterwards (eg, she's not conducting a deception), I'd rather she just tell me "it's over, it's not working," and leave out the details. That said, others may disagree with my ethics.

2) Do not do this in public. It's pretty awful to make someone be upset, or start crying, when there are others around. Her place is best, so you can leave and she won't have to make her way home upset, assuming she is.

3) If Henry can't get it through his head that he and Jane are over, "talking to him" probably won't work. Just go and date Jane, and either he'll figure it out, or he'll continue to be a problem and you'll deal with that in other ways. But "Sorry buddy, you're out of the picture, I've taken over" is not probably not going to change his behavior.
posted by Tomorrowful at 1:28 PM on November 1, 2010 [1 favorite]

...and won't have to worry about getting home in a wreck-y state.

This is worst-case-scenario, of course. She might just shrug and say "alright" and that'll be the end of it. Unless, of course, you tell her you cheated on her which will almost ensure the worst-case-scenario response.
posted by griphus at 1:28 PM on November 1, 2010

1) Break up with her. You made a huge mistake, but if you were really going to break up with her anyway eventually (whether or not you actually do), the kindest thing to do is to just end it without drawing her into your drama. If you guys are in the same circle of friends, it's going to be awkward enough without this. It's not the noblest thing, but that ship, to be honest, has sailed. And you can't get back on it.

2) The best way to do this is in person. I think the best place to do it is your house, so she can leave or stay as she feels comfortable. It's icky but do it quick.

3) I know Henry is your friend and that you wronged him. But really, this is Jane's responsibility. Honestly, I don't think it does anyone any good to tell him. But if you must, you should make sure that this is Jane's take on this too, or your new relationship may be a very short one.
posted by MCMikeNamara at 1:30 PM on November 1, 2010 [1 favorite]

1. Don't tell her you cheated, unless you think there is a good chance she will find out through mutual friends. If the Jane/Sarah social circles don't overlap at all, then its kinder to omit that fact when you break up. If she may find out from others, then it would be better to own up so she doesn't find out from a third party. If no-one but you and Jane know what happened then there is no need to confess.
2. Her place if possible, definitely not in public.
3. I can't comprehend the idea that you should talk to Henry. This is coming from a female perspective, so perhaps there is some bizarre set of guy ethics I'm blissfully unaware of, but I don't see that it is your place to talk to him. Its between Jane and Henry.
posted by Joh at 1:34 PM on November 1, 2010 [1 favorite]

i agree on the not telling - unless...

is sarah part of the same group of friends as jane? because if she is, when you and jane hooked up isn't going to stay a secret.

i can't think of any good, non-sexist reason to sit down with henry about jane.
posted by nadawi at 1:35 PM on November 1, 2010

1) I believe you should be honest about cheating if you plan to continue the relationship but if the relationship is over then the truth is hurtful to them and (selfishly) only makes you feel better - especially if you then plan to be with the cheater.

2) Miko had an excellent comment about how to break up with someone. Her place would be best.

3) Why are you talking to Henry (I mean, beisdes friendly chit-chat). Are you looking for his approval for your relationship? Because it isn't his to give. Is is about how he has treated Jane since they broke up? Because Jane needs to put on her big girl panties and have that conversation herself and decide how to act if he doesn't get the message. Do you want to rub her rejection in his face *oh I am happy jane choose meeeee!*? Because that is just mean.
posted by saucysault at 1:37 PM on November 1, 2010

A dispassionate answer:

Two months and you didn't click? Sure it was shitty to cheat on her, but where you really pay for such behaviour is in your own future relationships. I'd try for a clean break, just break up with her for your other real reasons without causing more grief than you need to on either person's part. A couple months of casual dating isn't a serious investment you need to make serious amends for.

As far as a place, if you are worried for your safety do it in public where you or her can make your own inconspicuous getaway after you deliver the message. I don't think there are any real rules other than a place where both of you will feel relatively safe and can leave alone on of your own accord.

I don't know why you're thinking about this Henry guy. By your description he and her gave it a shot, it didn't work out like things often don't, and she cleanly broke it off. The problem isn't Jane and your relationship but this guy's emotions overstepping boundaries independent of you or the girl. You have nothing to feel guilty of especially if he makes a scene, but if you think the best thing to do would be let him know discreetly ahead of time I wouldn't do it with the 'object of affection' in tow, that sounds a bit rough for anyone to deal with.

There is no '100% perfect score!' answer here, that's only in games not life. Chances are your relationship with Henry is toast but I wouldn't sweat that since you've already made your decision regarding that issue (and it's fair to say it is the right one).
posted by BurnMage at 1:38 PM on November 1, 2010

1) you were only dating sarah for two months, and it doesn't sound like it was especially hot and heavy so there's no need to tell her you cheated on her. it sounds like you were thinking of ending it at some point anyway, and getting together with jane just cemented your (non)feelings for sarah.

2) her place.

3) also in the camp wondering why you would need to tell henry. he dated jane; it didn't work out. it's not like they were hot and heavy. if you feel the need to say something and if he's more than a friendly acquaintance, then maybe next time you happen to see him (sans jane), you might want to casually mention that you and jane have started seeing each other since you know he'd been interested in her in the past. he'd probably have found out through your social circle by then.
posted by violetk at 1:43 PM on November 1, 2010

Don't tell her, nothing good (for her or you) comes with that. Do it quickly and kindly.

It depends on what kind of person she is. I'd prefer a public place, ideally not one of my favorite places or somewhere I've been dying to try, so if I never went there again I wouldn't care. I disagree with the do it at her place idea, I'd be kind of annoyed that you chose *my house* as the place to break up.

I'd tell Henry, after you break up with Sarah, and I wouldn't tell him you slept with her either. Don't bring Jane. I think it's nice to address it directly with him, right up front.
posted by mrs. taters at 1:43 PM on November 1, 2010

You are not going to try to date Henry, so you do not need to talk to Henry.
I can't comprehend the idea that you should talk to Henry.
i can't think of any good, non-sexist reason to sit down with henry about jane.

This your chance to say something like "hey, I want to start dating Jane again, but you know our friendship is really important to me..."

You're going to date her no matter what his reaction, but as a good friend you might at least give him the courtesy of having been listened to.
posted by esprit de l'escalier at 1:45 PM on November 1, 2010

As someone who dated a person that a friend was interested in, I say don't leave Henry in the dark. Don't ask his permission either. Just let him know that you'll be dating Jane. Don't be mean about it, but be sure not to give any hint that he can change things either.
posted by theichibun at 1:47 PM on November 1, 2010 [1 favorite]

I agree with mrs. taters on everything.
posted by esprit de l'escalier at 1:49 PM on November 1, 2010

Assuming you haven't had sex with Sarah after sex with Jane, I think you'd do her a favor by just breaking it off with out mentioning the cheating. Don't let her think things are going OK for another day. When you ask her to meet you, phrase it in fairly unambiguous terms that you need a serious-and-not-in-a-happy-way conversation. Break up at your or her house is probably a good idea for 2 months in—it'd let her save some face if she cries a bit or wants to yell at you a bit.

Do her a favor, remove her access to your social networks (like FB) so she won't see cutesy photos of you and Jane the day after you dump her.

With Henry, I'd say do it alone first. Phrase it in ways like "we're going to start dating, and I want to make sure things stay OK between us knowing you had dated for a short time in the past." You don't need to let him know that he's been creepily keeping a flame for Jane. Again, let him save some face. Go in with the assumption that Henry and Jane made a clean break, he's a good guy, and you want to stay right by him while starting to date an Ex. You're not asking permission, you're informing and apologizing for any discomfort.

If you and Jane both meet with Henry you'll put him of the position where the only thing he can reasonably say is "congrats to you both!" when he's probably thinking something more like "fuck you guys! I wasn't expecting this today."

Good luck, none of this will be fun or easy, but its the right thing to do. It sounds like you, and everyone else involved, are reasonable mature people, and can deal with things like this given some time and space.
posted by fontophilic at 1:52 PM on November 1, 2010

Go to Sarah's house. Do not make her go to any effort just to be dumped by you. This is also one of those rare cases where you don't really need to let her know about your indiscretion. It's just not working with her, and that's why you're ending it.

Why the hell does Henry have to be involved? It's Jane's life. She called it off, and if he doesn't get it, then it's her job to explain it to him again (without you there). If Henry is being truly creepy, it's also the police's job.
posted by katillathehun at 2:19 PM on November 1, 2010 [1 favorite]

Dude, hate to say it, but you're being creepy. Your job is to break it off with Sarah. Jane has to deal with Harry on her own.

Why you would opt for the extra drama of being involved with dealing with Harry is beyond me and should be a subject for therapy.
posted by Ironmouth at 4:19 PM on November 1, 2010 [3 favorites]

Plus ten million to what Ironmouth and katillathehun said. You do your relationship exit interview; let Jane do hers. If Harry gets angry with the two of you once you are officially dating, that's Harry's problem. You are not going to be able to negotiate Harry out of his anger.
posted by Sidhedevil at 4:46 PM on November 1, 2010

Did you guys read the part in the question where he's friends with Henry and Jane isn't talking to him?

Jane is not going to say anything. You think she's going to call him up and say "Hey, I know you've had a crush on me for a while, but I'm going to start dating your friend..."? Obviously not.

So, if you say nothing to your friend, then how is he going to find out? You go out for drinks with him or end up at the same party or whatever and you decide to avoid the subject altogether? You come across as conniving when he finds out. Or else he mentions how he hasn't seen her in a while and you say, "oh, by the way, I've been meaning to mention that...." You come across as secretive.

Also it's not misleading to phrase it in a way that suggests that you are balancing your friendship with your new relationship. Obviously, you're going to choose her, but you want to make it obvious to him that you care how he feels about it — even though it changes nothing. It's like when your manager asks you what you think about moving your group to a different location. He's actually telling you that you will be moved, like it or not. Asking is a polite way to make you feel listened to. Even if Henry misunderstands the subtext by demanding that you not date her — then you know where you stand with him, and you also know that he's not extremely bright.
posted by esprit de l'escalier at 5:13 PM on November 1, 2010 [2 favorites]

Only tell Sarah about the cheating if you slept with her after sleeping with Jane (as in, she might want to be concerned about sexual safety questions). Otherwise, follow Miko's advice in the link above, be kind, and move on. It wasn't the ideal order in which to do things, but that's life.
posted by Forktine at 5:23 PM on November 1, 2010

agreeing with the consensus here that you shouldn't really go into the details when breaking it off with Sarah, and that you don't really need to discuss it with Henry. I just wanted to add that it would also be a good idea to take it easy about how publicly you and Jane are about your relationship for a while. I'm not saying that it should be secret, but being very openly lovey-dovey will very likely cause hurt feelings and drama.
posted by 5_13_23_42_69_666 at 5:40 PM on November 1, 2010

Arrange for all four of you to attend something like a fancy art opening. Each invite a few friends from everyone's crowd, bonus points for ex's. Once you're the center of attention... never mind, everyone else was giving such good advice.... well there are options.
posted by sammyo at 6:04 PM on November 1, 2010

Did you guys read the part in the question where he's friends with Henry and Jane isn't talking to him?

No. Where did you see that? What I saw was that Henry and Jane dated, Jane says she told Henry it wasn't working out*, Henry is apparently still hoping it will work out, someone (either Jane or the OP or both) characterize the situation as "creepy".

I didn't see anything about Jane not talking to Henry.

*Which may or may not be accurate, and/or may or may not have been a message that was effectively conveyed to Henry. I say this as someone who once had a date with a guy she thought was divorced interrupted by the woman who thought she was still in a happy marriage with him; I don't know who was wrong in that situation, but it wasn't me.

The OP only knows what Jane said she said and what she said Henry said, and perhaps what Henry said he said and what he said Jane said, but not what actually happened, and my guess is that Jane and Henry have radically different stories of this.

If what Jane says is accurate, and Henry isn't respecting her boundaries after "several conversations" about breaking up, I would suggest that losing Henry's friendship is inevitable no matter what.
posted by Sidhedevil at 6:09 PM on November 1, 2010

Did you guys read the part in the question where he's friends with Henry and Jane isn't talking to him?

Er... no. I didn't. Where did you? Do you have inside knowledge or something? 'cuz the part about telling Henry sounds like the OP wants to rub it in Henry's face that he's got the girl now. It doesn't matter if Jane's not talking to Henry or not. The OP wasn't the one dating him, and if H is really causing problems, then why is the OP still friends with him?
posted by katillathehun at 6:38 PM on November 1, 2010

Here's the part about Henry being a friend:

She was inside of my immediate circle of friends, and so a mutual guy friend (Henry) decided to try to date Jane.

I don't know how close he is to this "common friend", but he's already assuming that he's going to talk to Henry, so I assumed that he is more than a passing acquaintance.

What matters in all of our actions is intent, and katilla is right that if the intent is to rub it in his face, then that's going to go badly no matter what. If the intent is to let him know that he values his friendship even as he steps over him, then I think that can go well in the long run.

I assumed that Jane was not talking to Henry if he was disrespecting her boundaries. How else can that work? It's not like they can have a regular chat about the SF Giants while she feels that he's being creepy. If she feels that way, she'll withdraw to give him the hint.
posted by esprit de l'escalier at 6:52 PM on November 1, 2010

Mod note: From the OP:
"Thanks for all of the responses so far. It's hard to talk about this to any friends, because I don't want to be spreading everyone's business all over the place, so getting outside opinions is terrific.

To clarify: Henry has continued to pursue Jane after she's said that she isn't interested. I've been friends with the guy for a while, and he's always been sort of unlucky in love, often going after girls who don't feel the same, and often putting a lot of effort into doing so. I think that, recently, he's gone beyond maladroit into creepy. It's hard to break off a friendship of 6 years, and I'm not sure how he's going to react when I tell him that Jane and I are dating. I'm going to tell him because with the nature of this group of friends he's going to find out. I'm not even sure what us not being friends would do to the friend group. I most definitely DON'T want to rub it in his face, but I don't see how I can go forward with the relationship if we don't talk."

posted by jessamyn (staff) at 6:52 PM on November 1, 2010

Wow, near-consensus here, not to be changed by me.
1) Don't tell her, just break up. I'm also in the "feel less guilty" camp, only because I'm feeling really old today, and so a lukewarm two-month relationship just doesn't seem to matter that much. If you do want to do a post-mortem on why you did it, that'd give you insight into yourself, which would be educational and potentially save you future mistakes. But it sounds like the other relationship wasn't working; this new relationship has always been meant to be; and after forty years of marriage and grandkids, who cares whether you hooked up with someone else one day before or one day after you broke up?
2) Let her choose. Say that you need to have a serious talk and ask whether she'd go out or stay in. After only two months, she might not care all that much, who knows.
3) You know your relationship with Henry best, but my initial reaction was "it's none of his business." If I was her and already feeling semi-stalked by the guy, I would actually appreciate your discretion. That said, it's your relationship to manage, and so maybe it'd be nice for him to hear it directly from you. I don't think I'd rush into it, though.
posted by salvia at 8:20 PM on November 1, 2010

1. After being cheated on with more than one guy, I can tell you, I would rather NOT know.
Some people disagree with this because she has the right to know and to get herself tested for STDs.
I personally get tested once a year and back when I used to date 4-5 guys a year, I would get tested after each one despite the use of condoms in many cases.

2. I am 99% the person that's dumped. I actually preferred it when it was online through an IM conversation if it wasn't a long-term relationship. I dislike confrontation. But that's just my opinion.

3. Don't talk to Henry. Let Jane figure that mess out. I mean, unless you guys are REALLY close. Then, well, you know him better than us.
posted by KogeLiz at 11:24 PM on November 1, 2010

OP, if Henry is being creepy to Jane, why do you want to be friends with him? I would think it would be awfully awkward at best.

I am presuming that you guys are all in your twenties or early thirties, just because eventually most people stop hanging out in these groups where everyone has dated or tried to date everyone else, but if Henry is really being inappropriate with Jane, shouldn't the rest of you have stuck up for Jane before now?

(This may be my own response to some past traumas speaking, so--I have been part of one of those friend-groups where there was the one sad sack guy who kept fixating on one or the other of the girls in the group, and the group dynamic was such that it was always about not hurting HIS feelings, no matter how uncomfortable the girl was made to feel or how inappropriately the guy behaved. Don't be that group.)
posted by Sidhedevil at 9:34 AM on November 2, 2010 [1 favorite]

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