By Baila Sebrow



I dated a guy for a long time, but then I had second thoughts so I broke up with him. He asked me why, and I wasn’t really sure what to tell him so I said that we are not a good match. I thought he took it well, because he said that he agreed with me. I was so happy that it went well, because I didn’t want to hurt anyone. Then I found out that he didn’t take it well at all.

From the next day on, I started getting calls from everybody I know that I made a mistake breaking up with him and that I should marry him. I figured that maybe he is lonely and can’t find anyone else to date, so I tried to set him up with other girls I know. He said no when I sent him their information, and that he only wants me. He shows up everywhere I go. I’m not exaggerating. If I go to my friend’s house for Shabbos in a different community, he pops up. Things like that happen so often that I know I’m not imagining it.

When I complain about this to people who are trying to convince me to change my mind, they say that he is being romantic. My married friends have even told me that they wish their husbands chased them like this guy chases me.

Nobody gets it, and nobody wants to set me up with anyone because they think that we are still together and that I’m just playing hard to get, that I’m not ready to get married, or that I am crazy to pass up such a great guy.

He is a great guy, but I don’t want him anymore. Does that make any sense to you? Do you think I’m the crazy one here?


I can’t vouch for the status of anybody’s mental health, including yours, but why would you make contact with a guy you broke up with if you want nothing to do with him? Why are you trying to set him up with other girls? If this were a typical breakup where the decision to end the relationship was mutual and you both agreed to remain friends, introducing him to others would make sense. There are couples who broke up, yet ended up introducing each other to different people, and marriages have even resulted from such match-ups. Evidently, that is not the case here.

You broke up with a guy who did not want to break up with you. He made that clear, but you then reached out to him to set him up with others. Moreover, you are surprised that he declined your offer. How did you expect him to respond? By thanking you and going out with those people? Not likely!

It is possible that your reason for setting him up with others was to get him off your back. Yes, such things do happen. But, in most cases, the jilted party feels even more hurt by such an offer, or worse—it gives the false impression that you are still interested and that this is your attempt to keep the lines of communication open.

Whenever I have a case where a single man or woman who ended a relationship wants to set that person up with somebody, I always instruct them to get a neutral party to make the introduction. Again, unless you mutually decided to keep in touch and assist one another, you made a huge mistake. If you truly do not want this guy back in your life, you have say what you mean and also mean what you say.

If this guy is pursuing you relentlessly, even though you told other people that you are not interested in him, that is not romantic. Why people would even think otherwise probably has to do with romance novels and movies. In those stories, they reunite in the end, and everyone lives happily ever after. That’s not real life.

In this universe, no means no, unless stated otherwise. Encouraging a man to continue pursuing a woman is enabling a stalker. Yes, if your account is accurate, it sounds like he is stalking you, and that is not cool. Stalkers are never harmless, regardless of how charming they might appear. There is a dark side that will come out sooner or later if allowed to continue. However, there might be a remedy to this saga.

I don’t know how new you are to the dating scene, or perhaps if you are a seasoned dater you may have never come across this type of situation. Dating is similar to a job interview. At times, it can be a long interview. The way one ends a relationship will often be the determining factor of the outcome post-breakup.

You dated this guy and you felt that he was not a good match for you. How did you go about ending your relationship with him? Did you have him believe that everything is going well, and one day out of the blue you decided to end things? That can be shocking and traumatic. Trauma can bring out different sides in a person, especially denial. When something bad happens, chas v’shalom, the initial reaction is shock, oftentimes followed by denial. It is possible that this guy may not even be a typical stalker but instead is in denial.

According to what you disclosed, you dated him for a long time, and you never gave him a real reason as to why you decided to break up with him. If you have established some sort of relationship with the person—meaning you dated for a while—then terminating that relationship is best done in person. You say that you thought he took it well. How do you know for sure? He might have missed the cues that you were definite in your decision. He may be assuming there is a tiny sliver of hope that there is still a future with you, and maybe he conveyed that to those who are trying to convince you to give him another chance.

In his head, he might believe that since you never gave him a reason, it is just that you developed cold feet, and with time you will come around. It could be that is why he is reaching out to others, and why he keeps showing up wherever you are. He may be hoping that if you run into each other enough times, you will reconsider. If you meant to permanently end the relationship, then it was on you to give him proper closure. Closure means explaining why you need to end a relationship, avoiding any vague answers. In most cases where there is healthy closure, both parties move on, and with time the pain lessens.

I am in no way justifying that he is making you feel uncomfortable. I just want you to look at what has occurred from various angles so that this does not happen to you again.

You had the right to terminate a relationship that you felt was not for you. Both parties have the right to determine to either go forward with a relationship or not. When he appeared to agree with you, it is possible that part of him had the same opinion as you, and that’s why he seemed unhurt. His feelings may even be mutual. Either that or he hid it well so as not to cry in front of you. I am assuming that when you initially ended it, you did it in person rather than by text, e-mail, etc.

How exactly did you end your relationship with him? Did you leave him hanging with the hope that perhaps in the future you would pick up where you left off? Oftentimes, those who break up with someone do so in an ineffective way that works against them. Just as it is important to know how to make a relationship work, there is an art to breaking up with someone in a sensitive yet firm manner. In most cases, breakups are mutual more times than people realize. However, it is how the breakup took place that will determine its aftermath.

If you have done everything right with regard to ending the relationship, (I’m still not happy that you tried to set him up with others) and he is unable to get on with his life, that is a serious issue. You need to concentrate on the people who are rooting for him to reconcile with you. Instead of making it seem that it’s about you, turn to them to help the guy. These people need to understand that it is harmful to him if they continue to encourage a union that will never be possible.

If that does not help you, or if he finds new people to reach out to, then make them understand that you are being placed in an uncomfortable position by having pressure placed on you. If you are 100% certain that you will never want to date him again, you need to sound sure of yourself when you tell them that no matter how hard they try to persuade you, you will never change your mind, and that you find their intrusion offensive. You also do not owe anyone an explanation should they ask you why you broke up with him.

Until now, this lovelorn guy was being validated and encouraged by do-gooders who felt that pushing you to go out again would help his wish come true. Hopefully, as soon as he sees that no one else will back his chase of you, he’ll weaken in his pursuit.

He needs to understand that following you around and showing up to places you go is not a good thing. If necessary, where you feel your safety is at stake, contact law enforcement. They might give him a warning, but if he persists, you may have to go the extra step of filing a petition for an Order of Protection.

You have the right to date other guys. I recommend that you find new social circles, specifically with people who don’t know about your relationship with that guy. Within those circles, find matchmakers who can introduce you to somebody. However, do not bring up the story about the guy you broke up with when talking to people who have no prior knowledge about that relationship. We live in a small world, and the frum world is even smaller. When you open a can of worms, you cannot control how many will spill out.

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. She can be reached at Questions and comments for the Dating Forum can be submitted to


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