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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.