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See this question for more context.

I plan on asking my friend Penny out. However, the tricky part of this situation is that Penny and my good friend Kyle dated for about a year. They broke up two months ago on good terms.

I developed romantic feelings for Penny around three months ago.

I don't want to ask Kyle's "permission" to ask Penny out because I believe that although they broke up on relatively good terms that Kyle could be spiteful and attempt to muddle things up. So instead, I plan on presenting him a fait accompli after asking Penny out if things work out with her. I want to ask for his "forgiveness" after the fact.

I don't want to hurt Kyle and I know that most likely this will hurt him in some way. I want to minimize the damage because I do consider him a very close friend.

My friendship with Kyle is casual in the sense that we never really talk about feelings/issues in our lives. It's mostly a friendship based on a mutual interest in technology and gaming, so conversations about relationships and especially something "dramatic" like this aren't something we're used to talking about.

How do I ask for his "forgiveness" if things go well with Penny?

I would appreciate knowing...

  • What tone to approach the conversation with
  • Phrases/words are helpful/detrimental to helping him understand/cope
  • How to deal with potential aggression/other emotional outbursts

I'm firm in my decision to use the "forgiveness" tactic. Also, I would expect Kyle to have the maturity level of an adult because he is one

Note: I have not asked Penny out yet. I just want to be prepared to have this conversation if/when the time comes.

EDIT: Although this isn't necessary, I'll try to provide a little more reasoning why I decided to go with the "forgiveness" route over the "permission" route. I'm a very anxious person. It's already hard enough for me to ask a girl out and I don't need someone potentially psyching me out of it. Kyle is my good friend, but given his feelings he might not be totally accepting of this situation which could easily make it impossible for me to ask her out. I know logically and emotionally that I want to ask her out, but in a way I have weak conviction. I want to set myself up for success with Penny and hearing my friend being upset about a decision that I personally find healthy and beneficial for me would make it a lot harder. I also have no idea if the feeling is mutual and would rather have my attempt go unheard if nothing happened.

EDIT2: A little more clarification. Although Kyle obviously could misinterpret things, Penny has told me exactly why they broke up (lack of communication, Kyle's apathy, and other such things) and he knows as well. In fact, I had suggested that they have a bit of a "postmortem" together to be honest and share more about what went wrong in a civil manner. They're both aware of why it happened and although it wasn't mutual they both ended up staying good friends. I understand Kyle may misinterpret my advances as "Wait, did we break up because of X, Y, Z or was it Steve?", but given how much honesty they've given each other, I doubt (although it could happen) he will think that I was involved (because I wasn't).

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Kyle, I am going to tell you something because I don't want you to be blindsided by it when you find out. Penny and I have begun dating.

You get the fact out there, you don't have to ask his permission, and you are being a good a friend as you can by making sure he hears it from you first and doesn't feel like you were keeping a secret about it.

If he asks when that started, I'd say however many days ago the date was. "Yesterday." I'd say a situation presented itself, she considered herself single, so you asked her, because you like her.

Don't make excuses or apologies, and don't discuss his relationship with Penny, and cut short any attempt by him to talk about that relationship. If there is anything he thinks is "wrong" with her, you'd rather find out for yourself.

You may lose his friendship anyway; some people will feel betrayed by this no matter how they find out. But this way, you avoid higher drama about keeping this a secret for months and basically lying to your friend.

  • 6
    If you don't want to tell him until after the fact, I think it's best to do it ASAP and like this. This minimizes the risk of him thinking you could've been a factor in his breakup with Penny... Otherwise if he finds out from another source, he could think "Wow, why didn't Kyle tell me... He must be hiding it for some reason??? Why???" and start looking for trouble. – Jess K. Feb 21 '18 at 19:34
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I highly recommend that you go and tell your friend before going out with his ex.

Even if you don't ask permission, at least let him know. This will be easier for you to explain as well as not creating any problems in the future.

If you are good friends, you need not worry. If you are not that good friends, just tell him that you like Penny and just wanted to let him know.

Though if you still want to tell him afterwards,

Hey man, I want to apologize to you... I have broken the Bro Code (be sad here, he will probably laugh at your seriousness). And it's serious, will you forgive me?

(he: oi no drama, stop acting serious, tell me the problem).

I went out with Penny on a date, yesterday. (pause, if he shouts at you and leave the room, trust me it is better, if only pause...) ...and I think i have developed feelings for her

(here he should ask how long has this been happening - downscale everything and tell him, it will be good--- But if he stays silent and tries to leave, tell him:) this all is a coincidence and has nothing to do with your fight. And trust me I am not being used against you, never will be used against you...

There can be silence or mild discussion or maybe heated argument at this point, you will have to figure out the rest by yourself. Only don't stress any point now.

The rest depends on the psychology of your friend. Try to spend more time with your friend circle than with Penny for the next week or so...

Hopefully he will get acquainted and it will go back to normal. Ask in comments if you want some more answers.

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Your friend is going to find out you're dating their ex sooner or later. You're going to be able to manage the message better of you are the one telling them instead of them finding out through a third party.

It's easier to keep it friendly if you "ask" in advance. If you say something like "How would you feel about me asking your ex out?" or "So I'm thinking of asking your ex out." you are explicitly not asking for permission but are still keeping your friend in the loop. One thing to consider is that you may be complicating things unnecessarily if their ex rejects you.

If you inform them after the fact. Framing it in a friendly manner becomes harder since you made this decision without talking to them. Remember you aren't asking, you are informing. Tell your friend "Yesterday I asked your ex out on a date. They said yes."

Your real concern should be how they will respond. Remember that there isn't a magic set of words that will guarantee a positive response. If they respond poorly be civil, respect the validity of their feelings, and remind them that while they may feel upset they don't have any claim on who their ex chooses to date.

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Good thinking to be prepared. If you've decided to tell him after the fact...

Do:

  • Be upfront
  • Be prepared for an angry reaction
  • Maintain your composure
  • Acknowledge and validate his feelings (you say he is a good friend, after all)

Don't:

  • Try to hide what's happening
  • Expect him to forgive you immediately (let alone be happy for you)
  • Tell him he's wrong to be upset

Find a time when the two of you can have a conversation. A quiet casual dinner wasn't the worst place to do it, but pick somewhere that you are free to leave whenever (so you/Kyle don't feel trapped, and can leave whenever the conversation indicates).

Give him the short version first: "Kyle, I wanted to let you know that Penny and I are dating." You want to sound respectful of his feelings, but not apologetic for your own actions (which would imply you did think you did something wrong).

Let his reaction guide whatever else you say. He may want more information (e.g. when did this start?) - he may not - he may storm out. Even if he reacts emotionally, stay calm yourself. Raising your voice or responding with anger will only feed into the feeling that this is an attack on him.

He may be concerned that you're going to learn intimate or otherwise private details about him via his relationship with Penny. If you and Penny have any ground rules regarding that, this is a good time to let him know and address those concerns.


My experience:

I was "Kyle" in a situation like this. "Steve" asked me to dinner, which was fairly unusual in the first place, and given how dodgy they'd been lately when "Penny" was mentioned, I had a good guess what was up. They waited until the end of dinner to actually spit it out though, after I started saying "well, good catching up, I should probably get going because work tomorrow..."

"Steve" finally told me then, and I was angry. My thought process was: I knew they had been hiding it from me, which meant they knew I'd be upset by it, which meant since they did it anyways without talking to me about it, they must not care about me. "Steve's" reaction was to berate me for being upset and remind me that I didn't get a say in who either of them dated. Technically true, yes, but only drove home the feeling that "Steve" didn't actually care how I felt.

I tried for months to talk it out with "Steve", thinking "maybe they just don't understand why this hurts me?" All I wanted was for them to actually reach out to me and acknowledge that I was hurt and upset by how they handled this. But they never did, and we are no longer on speaking terms. Don't be that Steve!


I realize this might sound a bit dire, but in the best-case scenario where he reacts fine, you can just breathe a sigh of relief and move on with your usual friendship. Just be mindful that - especially with the timelines - he may not have fully processed the breakup yet and may need some space and time to get used to the idea of you two dating.

  • I appreciate your anecdote. I really, really want to avoid making Kyle feel like he wasn't considered or that his feelings aren't valid and seeing it from the perspective of a "Kyle" is really helpful. Is there any kind of language you think would be helpful in particular to making sure Kyle feels acknowledged? At least, in your experience what would've been nice to hear? – Arthas Feb 21 '18 at 16:13
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    @Steve Hm, I don't know about exact wordings, I think the biggest problem for me was overall lack of empathy. Like I didn't expect "oh, I'm so sorry you're upset, we'll stop dating now", but I was hoping for at least "I'm sorry, I understand this is awkward, what can I do to make it less awkward for you?" - showing that my feelings were valid and not pretending this was a-ok normal and I was crazy.. even "ok, I see you're upset, I'm sorry for upsetting you" would have been better. – Em C Feb 21 '18 at 16:35
  • A lot of it is situational really.. my situation was more complicated and there were a lot of unanswered questions that "Steve" didn't address and/or got angry at me for asking. But in yours it may be more straightforward. – Em C Feb 21 '18 at 16:39
  • Thank you for sharing more. I suspect my situation is much more straightforward since there was no monkey business or romance going on before their breakup, but knowing how it must've felt from the perspective of a "Kyle" is REALLY helpful in preparing to talk to him about this. – Arthas Feb 21 '18 at 16:41
  • @Steve glad to help! It sounds like your heart is in the right place here and I wish you luck :) – Em C Feb 21 '18 at 16:43
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I might be off target here, but would it be fair to assume that Penny and Kyle are both adults (or, at least, old enough to make their own decisions)?

Kyle doesn't own Penny, and if she is happy to go out with you (you don't even know if she is interested in you, right?) than that is between you and her.

If the case is that Kyle and Penny announced their breakup publicly, and privately decided to try again in a few months, then it is up to Penny to explain this to you - if she shares your feelings.

Don't try to over-analyze the world, and don't assume that you have to do the thinking and decision-making for everyone you interact with.

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I think that some of the other answers cover the ground pretty well (particularly Amadeus').

But I wanted to point out something that I think hasn't gotten enough emphasis: I'm not sure that "forgiveness" for asking Penny out is really what you care about. After all, you are intending to do so whether or not Kyle would be OK with it (in your question you said that if Kyle reacted poorly, were you to talk to him about it first, you might not ask Penny out due to your nerves and not due to anything he thinks or feels). And no, no amount of bland assumptions that he probably would be OK with it because they broke up on good terms is a substitute for talking with him to learn how he actually feels.

It sounds more like you want there to not be conflict over you pursuing something you want, and that sounds reasonable to me. Kyle doesn't have any claim on Penny's dating life anymore and the relevant issues are probably more around how your group of friends interacts in the future.

You know yourself much better than I do, and if your anxiety is such that this is the only approach you can take then so be it. But if you try an apology (rather than an approach like the one suggested by Amadeus) the apology should maybe be focused on your disregard (necessary or otherwise) for Kyle's feelings in the face of something you want for yourself moreso than the simple fact of trying to date someone he's no longer with.

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Lots of good clean answers here and thought to add a different side not really talked about...

As with many things, there is usually an unwritten law between male friends that you just don't date another's ex... it's "bro code". But of course, there are always exceptions to that.

Most of the time it's a waiting period of a few months... (depending on how long they previously dated for), other times, when you are all hanging out, it just organically happens and the group accepts this new course in life (especially if they all remained friends after the break).

As many people said, it always comes down to honesty as the best policy. I found myself in this situation once and chose to ask my friend first which he replied that he didn't care and saw it coming anyway.

I understand your hesitation with asking your friend first. I too struggle with even getting the courage to ask someone to dinner, but here is where I may say something probably not popular but still needs to be thrown out there.

Due to your difficulty with women, you are presented with one who is now a known single, and better yet, you know what her issues with the breakup are. You have an easy checklist of what to avoid and how to "swoop" in being everything she complained about with her previous boyfriend. You are familiar with her and probably have hung out with her a bunch being the circle of friends situation. So she is "easier" for you to approach than in other situations.

What I am trying to get at is, the feelings may be formed for her for the wrong reasons and may just be trying to cause you think she is easier to obtain as a girlfriend due to you knowing the shortcomings of the past relationship and feeling that you can show that as your strengths. If a friend getting upset is enough to cause you not to chase after a single woman, then I would have to question if you truly cared for her enough or not.

From the way you have described your friend you said they are a good friend, but it sounds like your friendship is superficial in that it doesn't go deeper than playing video games together. At some point, you will need to decide if she is worth possibly losing a friend over or realizing that the situation is rooted in a deeper issue that should be addressed. My gut tells me it is the latter.

Whatever you end up doing good luck and I hope it turned out well! I know my answer is several months later but I felt like no one addressed an alternative viewpoint that the feelings could be drawn from other intentions.

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The one important thing is to tell him with the minimum necessary amount of details, because these are what stings. "Since when" is usually one of the necessary details - if the breakup is recent they will want to know if it started before or after. That's one reason why it's usually recommended to tell him before rather than after.

Also relevant: depending on the cultural context, 2 months after the breakup can be insultingly quick to find new love. This may or may not apply to the relevant subculture in your case, just keep your eyes and ears open to understand what the custom is.

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