I recently broke up with a guy (let's call him Tom) that I had only been casually dating for a couple months. During this time, I had what I thought was simply a crush on a co-worker for a while, but realized my feelings were stronger for the co-worker than Tom and decided to break things off. When Tom and I broke up, I simply told him that I lost feelings for him (which was true) without telling him I liked someone else just so I didn't hurt him more. But eventually, he asked if there was someone else and I wanted to be transparent and honest because I felt he deserved that much respect and told him about the feelings I had for this co-worker.

I still wanted to remain on good terms with Tom because we were friends before we dated. I understand that's difficult right after a break up so I gave him his space. Yesterday, he asked me if I was going to pursue a relationship with this co-worker. I was shocked that he asked and asked why it mattered to him. He didn't respond but told me if I dated this co-worker it would be as bad as cheating on him because I thought about him during our relationship. He also said he would not remain friendly with me unless I did not date said co-worker.


I feel bad for hurting Tom and don't want to hurt him more by dating this co-worker but at the same time, I really like this person and don't want to feel like I can't do something because my ex-boyfriend is telling me not to.

How do I tactfully communicate with Tom that what he's saying is out of line or that he cannot control the decisions I make?

  • 45
    Has your ex-boyfriend controlled you/your decisions in other aspects of your life before?
    – ElizB
    Commented Aug 2, 2018 at 15:44
  • 2
    Sometimes he would make what I thought were unreasonable demands, but we didn't date long enough for him to attempt anything too drastic such as I felt this was.
    – user19898
    Commented Aug 2, 2018 at 15:45
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    Please don't write answers in comments. it decreases the quality because there's less control on comments and this comment will likely be deleted. You're welcome to post an answer to this question and expand on what you want to say.
    – ElizB
    Commented Aug 2, 2018 at 15:55
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    Please add your expectations of "casual" dating concerning Tom, and also of what you define as a "crush" as opposed to "stronger" feelings, since you claim to have had had these "stronger" feelings for your co-worker prior to Tom being your "casual" dating partner, and only just understood. Note: I agree you should not be involved with Thomas any longer. He does not belong to you.
    – NOP
    Commented Aug 3, 2018 at 3:02
  • 2
    Was it made clear to Tom that this was 'casual' dating and not something serious?
    – Pharap
    Commented Aug 3, 2018 at 3:47

15 Answers 15


This is not a situation where tact is likely to help anything. Tom sounds hurt, maybe fairly, maybe not, and he has apparently decided that not only will he nurse that feeling but that you must tend to it as well.

Your relationship ended, and whether or not that was primarily because your feelings towards Tom changed or because you developed stronger feelings for someone else is less important than the fact that you didn't want the relationship to continue. Tom (seemingly) feels that your co-worker was in some way the cause but that's an irrelevant detail.

Tom, we dated for a while and it didn't work out. I didn't cheat on you, and when I thought our relationship had run its course instead of cheating on you I decided to end it.

He's not entitled to date you, nor to control what you do. But, at the same time, you are not entitled to Tom's friendship, nor to his feelings being what you would prefer them to be. You've already made all of the relevant decisions here, and now it's Tom's decision how to deal with his feelings. The most you can do is to be clear and to accept Tom's decisions.

  • 6
    Thank you for the advice. I agree that I cannot demand Tom feel a particular way or expect him to be friends with me because I did hurt him. However, I would like to be civil and explain that I don't think it's fair for him to treat me this way or put ultimatums on who I can date now that we've broken up in the most tactful way possible. I'll take into consideration your advice next time I talk to him. Thanks again!
    – user19898
    Commented Aug 3, 2018 at 15:23
  • A statement of the form "If you date X, then I will not be your friend any more" is different than "If you date X, then I will take your air supply away". Air is a right and so threatening to take it away is coercion. His friendship is not a right so threatening to take it away is not coercion. One way to look at this is that Tom has just notified you of his policy. Perhaps it's not intended as a punishment to shape your behavior, but just disclosure of the fact that he won't be able to be friends with you while you date the coworker. Commented Dec 2, 2019 at 19:40

You're going to have to just say it. There is nothing you should do to ease him into it. Hiding the fact that you are dating or something else like that would possibly hurt Tom even more than if you were honest, if he found out.

Tell him exactly what you said in your question. "What you are saying is out of line and that you cannot control the decisions I make." If he gets angry about it and won't talk to you, then that's his problem.

Speaking as someone who has once before been in Tom's place (albeit not as angry/emotional about the situation), if you were being ambiguous and didn't tell me the truth, I would have been more upset. I could get over the fact that you left for someone else, but not if you lied about it.

  • 8
    @MichaelRichardson The OP did leave because of feelings for another coworker (see the first paragraph) and the last sentence isn't referencing the OP specifically. It's referencing what I would say/think if the OP lied or was intentionally unclear about dating the other coworker. Commented Aug 2, 2018 at 18:43
  • How did OP lie exactly? Commented Aug 2, 2018 at 20:53
  • 12
    You might want to edit this to make it clear that you don't think the OP lied, but that lying to Tom in the future will make things more difficult. Your last sentence is referring to the hypothetical, but at least 2 people have been confused by that.
    – GreySage
    Commented Aug 2, 2018 at 21:54
  • 1
    People are stressing over the distinction between lying and purposely hiding the truth. Perhaps we should split the difference and call it "being deceptive" or "being less than honest", or perhaps "hiding the truth"? I think the point of this answer lies in the intent of it, not the letter of it and that point is that deception is often more hurtful than a painful truth.
    – Pharap
    Commented Aug 3, 2018 at 2:11

Setting and respecting boundaries is really important for healthy relationships. I think this is a good opportunity for you to set boundaries with Tom. As far as who you are dating in the future, simply tell him something like:

I value your friendship and hope we can remain friends, but who I date in the future is my decision and not yours.

As far as his concern over whether or not your attraction to someone else while you were dating is cheating - I don't know how invested you are or should be in convincing him otherwise. All you can do is tell him that nothing happened and attempt to help him see your point of view.

I don't believe that exes should be hostile to each other, but in my experience people rarely stay friends after dating because:

  1. When a relationship ends, both people usually aren't over it at the same time; in your case Tom isn't as past it as you are. Your friendship - for him - still includes a desire for a romantic relationship.
  2. As people move on and date new people, the new girlfriend or boyfriend usually isn't happy to see their counterpart hanging out with their past flame.
  3. In almost all cases the pre-dating friendship was heavily influenced by an interest in dating at some point, and in many cases there isn't much of a friendship left once the romantic interest has been taken out.

Short answer: Your friendship with Tom has ended. I would tell him this:

I really do want to pursue a relationship with my co-worker. I regret that we can't be friends anymore, but I've made my decision, and I'm going to stick to it.

Long answer: I can only speak for myself, but I'm sure many men and, presumably, Tom feel similarly. We make efforts to control our emotions. When we're in a relationship, we make an effort to focus our feelings and attention on the woman we love. So when a woman breaks up with us and the only reason is that her feelings have changed, it tells us that she has not made that same kind of effort and that she is not able to make serious commitments. Tom feels betrayed, because his primary expectation of you has been nullified.

I've been in a similar situation (though I did not react the same way), so I'll tell you what I think is going through Tom's head. Yes, it's entirely possible that he doesn't understand his own feelings, but I'll try to explain what he's doing anyway. I hate to pretend to be a mind-reader, but I think it's important to bring up these possibilities:

Yesterday, he asked me if I was going to pursue a relationship with this co-worker. ... He ... told me if I dated this co-worker it would be as bad as cheating on him because I thought about him during our relationship.

He probably brought this up, because it's the best explaination he could think of for why you can't be friends anymore. He probably never considered what would happen if you broke up with him so abruptly, so now he can't figure out why he doesn't trust you anymore.

He also said he would not remain friendly with me unless I did not date said co-worker.

This is certainly a mistake on his part, because he doesn't realize how difficult it will be for him to trust you again. He's trying to leave you an option that he thinks will make things better.

How do I tactfully communicate with Tom that what he's saying is out of line or that he cannot control the decisions I make?

The way to not be controlled is to be firm in your decisions and to realize that you can't always have it both ways. (See short answer for what to say.) You neither need, nor are entitled to his friendship. If you can let go of him, which you will need to do, then he has no hold over you.

Finally, I would avoid framing his actions as an ultimatum. It's likely that he's handling a tough situation in the best way that he knows how, and that he doesn't know that you're attached enough to think that ending the friendship is a punishment.


Making boundaries is your best bet. Depending on how resistant he is to criticism, you can approach this a few ways. From your answer to the comment, I am making an assumption (I may be wrong) that he may be an emotionally abusive person. Be cautious in your approach.

If he is resistant to criticism, it is best not to give him ammunition to control you any further. What you said in your question is an excellent statement.

Tom, what you said to me about not dating this co-worker was out of line. I can make decisions for myself. Don't tell me that I can't do this just because you wish it so.

Then walk away. If he persists in making demands, do not engage him. If he starts apologizing, simply and directly accept the apology and go date the co-worker, because there is absolutely nobody that can control your choices but YOU. He cannot do anything about that.

If he is more receptive to criticism, you can approach him a little "softer".

Tom, I know that you're hurting now, but this is my choice. Please be happy and know that I'm okay. I wish you all the best and please don't judge me on my choice of romantic mates.

It's better not to talk about the fact you are having feelings for the co-worker in front of him until his better reasoning kicks in, because when emotions kick in, it is reasonably hard to keep a steady logic for words and actions, increasing the likelihood of him saying something crazy or demanding, or hurtful because he is reacting to being hurt.

The overall goal here is to keep a steady stance on your decision, and make it firm that he won't sway you or make you cave in. It seems he may try to emotionally guilt-trip you, so watch out for that.


My first try would be to simply ignore Tom on this. People are often bitter after a break-up. I wouldn't hold this against Tom. He presumably had strong feelings for you and you hurt his feelings. But I wouldn't let it stop you from dating someone else, either.

If he persists, I'd politely say something like, "I'm sorry, Tom, I'm not your girlfriend any more, and I can date whoever I like."

It may well be that your friendship with Tom is over forever. It's pretty classic that when a girl dumps a guy, she says, "let's still be friends", but the guy doesn't want to be friends. He wants you to be his girlfriend or he doesn't want you in his life at all. If that's the case, you're not going to argue Tom into being your friend any more than he's going to argue you into not dating this other person.


How do I tactfully communicate with Tom that what he's saying is out of line or that he cannot control the decisions I make?

"I'm sorry to hurt you, but this is my life and my decision to make."

This will likely end your friendship, and that is his decision to make. The same way that he cannot control who you date, you cannot control who he is friends with.

Relationships are a dirty game and as a man, I honestly have no idea where women get this idea of "staying friends". To us men, that sounds and feels like any deeper feelings weren't real. Going back to friendship after a relationship attempt is something that sometimes happens by itself, but almost always depends on both parties realising that a relationship doesn't work and being friends was better.

If you break a man's heart, you don't get to keep the pieces.

My namesake doesn't mean what he says. What he really means is: "I still love you and this hurts me, so I'll go away and quietly cry in the corner."

You will not be able to have an ex-boyfriend-now-friend and a new boyfriend at the same time. Men don't work like that. Time might heal those wounds, but at this time, give him space, forget about the friendship, and if you are lucky, one day in a couple of months, he may come back, after he's dealt with his feelings.


Basically your Ex is accusing you of starting another relationship (To whatever degree) before terminating your current one.

Only you know whether you crossed any lines before terminating the relationship. (I.e. Things that would have either upset him, or you would know better than to do in front of him are Red Flags. Examples might be flirting in either direction, intimate conversations, etc.)

As others have said honesty is better than tact at this point. He's hurt, and feels that this other guy came onto at work (Likely knowing you had a boyfriend. Warning: If this guy came on to you knowing you had a boyfriend, that is a really bad sign.) Be strait, apologize for hurting him, apologize for any flirting / inappropriate behavior you did or failed to put a stop too.

The ultimatum, might simply be because he feels stepped on, but it sounds to me more like he's trying to control you, and if so, that won't change. It can happen in rare instances, but when you date friends they typically are not going to remain friends afterwards. Most people are simply too jealous.


This is a very tricky situation indeed. On the one hand you don't want to upset Tom further, but on the other hand you shouldn't give up on having a relationship because someone is giving you ultimatums.

It's quite likely that you will have to choose between Tom and your co-worker (let's call him Jerry).

Before you decide what to do, put yourself in Tom's shoes. (Please bear in mind that this is a partially hypothetical scenario.)

Presumably he thought the relationship was going well and perhaps didn't think it was as 'casual' as you did, perhaps he thought you two had a future. (Perhaps Tom doesn't even have a concept of 'casual' dating, some people don't.)

Then you broke up with him and you told him that this was because you had "lost feelings for him". You neglected to mention that you had found someone that you were more interested in because you believed this was somehow 'protecting him'. Tom is at this point probably very hurt.

He believes you have fallen out of love with him and he's most likely confused about why. He tries to find a reason for this, something to blame. Eventually he concludes that there must be someone that you're more interested in. He asks you about this and you admit that you concealed the truth from him.

Tom has just simultaneously discovered that not only was there someone that you were more interested in, but also that you concealed the truth from him (some might even class that as lying, either way it's a form of deception). Now Tom is even more hurt than before. You have hurt his trust by lying to him, and he now has an object on which to direct his hurt and hatred - Jerry.

Now that he knows you lied about it, his trust has been irreparably damaged. He's probably beginning to wonder whether you're still be hiding other things from him. He might even believe that there was more going on.

Like many people who feel wronged, he wants 'justice' - he wants those who he feels are responsible for his pain to be 'punished' for it. He is manifesting this with his ultimatum. He probably thinks that by preventing the relationship with Jerry from happening, it will make him feel better and will somehow provide him with 'justice'.

He is of course wrong to try to impose his will on other people, but when considering his point of view, it's understandable that he's letting his emotion get the better of him. Letting go of someone you like is hard.

Reluctance to let go of either person is the whole reason that you're asking this question. You don't want to let go of Tom or Jerry.

The fact of the matter is that there's nothing you can say here that will quell Tom's feelings. In his mind he's set you an ultimatum and he will enforce that ultimatum.

If you are sure that Jerry reciprocates your feelings then you absolutely should get together with Jerry. You should tell Tom that you want to remain friends but if he no longer wishes to remain friends then that's the way it will have to be.

The reason Tom sees his ultimatum as a tool is because he believes that "not being friends anymore" is a significant enough threat that you won't take that option. If you show him that you are willing to accept that condition, his threat is empty and his ultimatum backfires.

If Tom doesn't try to contact you to say that he regrets his ultimatum and wants to stay friends, then you must be prepared to let go of him. Perhaps someday you will reconnect, but until then you must try to forget about him and focus on your decision to be with Jerry.

If Jerry does not reciprocate your feelings then the objective changes somewhat. Forming a relationship with Jerry no longer becomes an option, and you're left facing a hurt possibly former friend who has forced an ultimatum upon you.

You must decide whether to try to reconcile and forgive his foolish threat, or to cut ties with him because of it. At this point you've both caused damage to your friendship, you by hiding your feelings for your co-worker, and him for threatening you with an ultimatum.

Either way you must make it clear to him that you aren't happy with his attempt to dictate your actions and that getting back together with him is out of the question even if you do remain friends.

He may end up deciding that if there's no hope of being 'together' with you (even when you aren't with someone else) then he might prefer to cut ties with you because it's less painful.

I'd ask that you make sure that Tom has someone who he can lean on for support after you've gone. The end of a relationship is a tough time that causes many people, men and women alike, to do stupid things that they regret. As many will readily predict, he might try to come back with a vengence (e.g. stalking, violence etc), but what many people forget is that he might alternatively fall into a deep depression and try to take his own life. Suicide is one of the biggest killers of young males.

Most likely he'll eventually get over it and move on with his life, but it pays to be aware of the less appealing alternatives. Good friends or a strong will/mind are imperative for preventing the negative outcomes.

Ultimately the thing to take away from all this is that secrets and lies are the best way to kill any relationship.

Be honest no matter how painful the truth is - if it's out in the open then you can deal with it openly and honestly.


This is a decision you have made for yourself. Just say that. There is no tact needed here. The more tact replies or explanations you give, the more emotional blackmail you would receive. You are not hurting Tom anymore. He is hurting you by putting you in a dilemma and trying to prove that you made an unethical choice.


In your shoes, I would:

1) Offer to have a conversation about Tom's feelings regarding the end of the relationship, in the interest of the platonic friendship we hope to establish. He sounds hurt and confused, and processing some of that with you might allow him some clarity & perspective. This might involve discussing your interest in the coworker before the relationship ended, and where exactly the line was drawn. I would probably include a sentiment along the lines of, "I believe it is human nature to become interested in people occasionally. In my mind, fidelity means not acting on those interests, rather than not having them in the first place - I don't think we can control these interests developing, just our actions. I thought I did well by you in recognizing that I wanted to end our relationship rather than trying to pursue those interests behind your back." He is free to disagree, of course, about whether or not that was the kind thing to do.

2) Tell him kindly that whatever happens between you and your coworker, or anyone else, is not up to him, and does not retroactively change anything about the way your relationship ended.

3) Offer him some space to process on his own. Tell him that his friendship is important to you, and you'll be available if he wants to reach out in the future, but you will not make any overtures until you hear from him.


To answer the immediate question... it's really none of his business what you do next, or who you do it with. He's out of your life.

When you break up with someone, discontinuing all contact is the easiest way for the other person to get over it - out of sight, out of mind. Since you did the parting, it might be easy to think you can be 'just friends', but to the person on the other end, that looks like you're leaving the door open.

A difficult thing to keep in mind - when you were together, you probably became accustomed to sharing common thoughts and moods. That's no longer the case: how he feels now is quite different from how you feel now, so you can't really gauge him like you once could.

He's not hanging around because you were the great love of his life - if you were, you'd still be together. He's probably doing it because his pride took a shot, and the simplest way to eliminate that pain is to get back together. Doesn't usually work, but that won't stop them from trying. I know... first time a girl tossed me off, it really smarted, and I made a fool out of myself. Only later did I realize that it was just hurt pride... we really weren't right for each other.

If you break up with a guy, you're going to hurt his feelings. Only time and distance will mend that. Maybe in a few years, after he has found someone else, you can resume being friends. Or, maybe never. Unfortunately, getting serious about a good friend often wrecks the friendship, if it doesn't work out. Those emotional scars don't heal quickly.

For now, tell him your dating habits are not something he should be concerned with. And, for his sake, fade to the background and discourage future meetings so he can move on and get over this. Out of sight, out of mind. Just because you can meet him with no romantic feelings doesn't mean that he can do the same.

It has been my experience that, with very rare exception, you really can't be friends with someone you recently broke up with. Just too many emotional conflicts... it will not end well.


I had a similar situation in which I tried to remain friends with my ex after a particularly messy break-up. At one point he said to me, and I quote: "If you do find another boyfriend, I'll stop being friends with you because I won't be able to bear that."

Moral of the story: he's just upset about you liking this other guy because he still has feelings for you. Even if you did "cheat" on him by getting together with this new dude, what the hell does that matter since you aren't together anymore? If anything, he should value that you respected him enough to break it off before you even tried something with this co-worker.


I am not sure, how I would communicate with him. However, I had a similar situation with my ex-girlfriend. And all I told her was in the vibe of: Whoever wins you over is the one who deserves you!

(They are a real sweet couple by now)

Maybe he needs his time to think about everything, but he is the one who is responsible to manage his feelings, not you. There is no need to make you feel guilty in his position. You where honest with him as soon as you realized it for yourself, that is all he could and should expect from you.

Keep that in mind, when communicating with him. :)


Let me start with a little background about myself.

I've been in a relationship with my ex for four years before I broke up with him. That is five years ago now, but the damage still lingers. I can see a lot of similarities between my situation and yours. I don't want you to go through the same.

In hindsight, my ex emotionally and sometimes physically abused me. I am an aspie and he would deliberately put me in situations that I have difficulty handling. He would then tell me I am an adult and should learn how to handle them. I don't think he did it on purpose, but he made me feel horrible about myself. I read uncertainty in your questions (I also read the previous one). Does Tom have a history of doing stuff that makes you feel bad about yourself, like making you admit cheating when you didn't?

I don't think my ex ever realized what he did. I think his motivations ranged from laziness to actually wanting to help me. I believe he really loved me. I didn't want to hurt him, so I allowed it to continue for four years. Three years in, I tried to break up with him, but he was so upset, I decided to stay with him for another year. I shouldn't have.

Please accept that you do not owe him anything. While you should not actively try to hurt him, you do not need to suffer to avoid hurting him either. His feelings are his feelings. You do not need to babysit them. I should have broken up with my ex when he refused to stay the night with me when I moved to a student flat in a big city (I'm from the countryside, and I was 17). I am glad you're not trying to make it work like I did, when it clearly doesn't.

When I finally broke up with him, he was really upset. He said things like "but I love you!". Remind yourself, it doesn't matter. An unbalanced relationship doesn't work.

While your coworker made you realize you needed to break up, I already broke up with my ex before I even met my new partner. I met him a week after breaking up with him. He started out as a really good friend. He listened to me being sad about the breakup. He helped me put my feelings straight.

He asked me to be his girlfriend a month after breaking up with my ex. That's when I received the message. "How long have you been cheating on me?". My ex wouldn't believe I did not cheat on him, even though I hadn't met my current partner until a week after I broke up with him.

That was 5 years ago. The friendship never returned to what it was before we started dating, but we are on friendly terms.

Before you have this conversation, reflect on your past relationship for a moment. You say you broke up with him because of a coworker. Is that really how it is? Think about that for a moment.

Imagine for a moment that your coworker does not exist, and forget about your ex's feelings about this. Imagine you are free to date whoever you like. Put the hurt aside for a moment (yes, that's very difficult). Are YOU happy you broke up with your ex? Your feelings, not your ex's. Be honest with yourself. Think about this for a moment before you continue reading. Maybe you don't have the answer yet. That's okay.

I am going to make a few assumptions here, but I have strong suspicion they are correct. In the end you broke up with your ex because your relationship with him didn't work out. Your coworker merely helped you realize it. Am I correct?

Now, on to your ex. What do you think he feels? I'm going to make a guess. He is upset because you broke up with him. He wasn't good enough for you. And even worse, someone else apparently is! He doesn't want it to be true, because that is easier. It hurts less.

Maybe he thought it would be even easier for him if you didn't break up with him and cheated on him instead. He is hurt. People who are hurt do things we do not expect. He had you as his partner for a few months. Losing that hurts. I assume it wasn't easy for you either. But you'll have to recover from that pain on your own and so does your ex.

You say

I feel bad for hurting Tom and don't want to hurt him more by dating this co-worker but at the same time, I really like this person and don't want to feel like I can't do something because my ex-boyfriend is telling me not to.

Don't let him manipulate you into admitting cheating. That is not good for your recovery process, nor for his. In fact, I think not hurting him more should not be your goal. If you were not cheating on him, but he wants you to admit you did, it sounds like he could use a wake-up call from his delusional stance. That will hurt him, but him believing you cheated or even left him for someone else is probably far worse for the future of your friendship.

Okay, super long backstory over. The answer is probably not what you want it to be. I'll try to summarize what I think.

  • Accept the possibility that your friendship is unrecoverable.
  • Not hurting him is almost impossible. He set up this awful situation by accusing you of cheating. You do not need to babysit his feelings now.
  • You do not need to please him, especially not at the cost of yourself.
  • Forget tact. He's long past that with his controlling behaviour.

I'd go for a clear message to him. Signal it is over and that it is because of him, your coworker is not relevant. Perhaps call him out on it.

Tom, it didn't work out between us. We should both move on and it is not fair on me if you try to control my life.