Dating
By: Baila Sebrow
Question
I hope you can help me with my problem and advise me on what to do. My roommate and I used to be besties. We’re both frum, we came from out-of-town, and really looked out for one another. We trusted each other with everything, and we always had such fun. I truly trusted that she always had my best interest at heart until a recent incident. I dated a guy very seriously and we were on the verge of getting engaged. We already even went ring shopping. From the very beginning of when we started dating, my roommate used to make it clear that she doesn’t like him, but I never understood why. She claimed that his jokes were corny and that he’s a flirt. One day she told me that he’s cheating on me with other girls and that he has that sort of reputation, and I would be crazy to marry him. It’s true that he does have a flirtatious personality, but I believed that he was true to me. She convinced me that he was cheating on me behind my back and that people were laughing at me. I ended up breaking up with him.
No sooner did we break up than she started dating him. I didn’t know about it right away, but she suddenly moved out and then I heard she’s now engaged to him! I feel so betrayed and hurt. I want to say something to him, to let him know the truth, because I still love him, but I don’t know how to go about it. I never would have broken up with him if not for my roommate.
Response
I’m very sorry for what was so unfairly done to you. What happened to you was not merely a breakup. It was the collapse of two relationships at once—an almost engaged one and a friendship that you believed was rooted in loyalty, trust, and sisterhood. In many ways, the betrayal of the friend may cut even deeper than the loss of the man, because when you made the decision to break up with him, you believed you did that with clarity.
You started off as two young ladies far from home, navigating the frum dating world together, confiding in each other, protecting each other—sharing secrets, dreams, and fears. In that kind of environment, roommates often become family. They see the tears after dates, hear the excitement after phone calls, know the vulnerabilities that no one else sees. You trusted her not only with information, but with influence. You believed she wanted what was best for you. That is why this hurts so profoundly. Your roommate positioned herself as someone protecting you while simultaneously usurping your place. That combination can leave a person questioning their judgment, their memories, and the ability to ever trust people again.
When your roommate voiced her concerns about the guy, you did not hear jealousy or hidden motives. You heard the warning of someone who cared about you. She told you he was flirtatious, unfaithful, dishonest, and embarrassing you behind your back. She painted a picture of a girl being fooled while others laughed in the background. Under those circumstances, many people would have done exactly what you did. Yes, anyone else would have panicked, questioned their judgment, and stepped away from the relationship.
But then came the devastating twist. Shortly after convincing you to break up with him, she began dating him herself. It doesn’t matter at which point she moved out, whether it was when she first started dating him or when her relationship with him got serious. This is a nauseating fiasco at best.
Of course, you feel shattered. Of course you are replaying every conversation in your head, wondering which moments were sincere and which were manipulation. You are likely asking yourself whether she sabotaged your relationship intentionally, whether he was involved emotionally before the breakup, whether people around you knew more than you did, and whether your entire reality during that period was built on falsehoods. Those questions are natural. But realistically, they may never all be answered.
The hardest part of betrayal is that it forces someone to realize that the person they trusted was capable of acting against their interests while pretending to protect them. This gets into the kishkas of a person and creates a kind of emotional vertigo. You have experienced trauma. I imagine where you’re holding now emotionally is that you begin revisiting old memories with new eyes, questioning everything anyone has ever told you. Compliments feel suspicious, advice feels strategic and manipulative. You wonder whether you missed signs that now seem obvious in hindsight. Please understand that whatever you’re feeling is normal considering what you’ve experienced.
Your roommate did a very bad thing, something she will one day have to answer to a Higher Authority. But before you place the entire blame on her, you must also be honest about the guy involved. You acknowledge that he did have a flirtatious personality. While that does not prove he cheated, it does suggest that your roommate’s concerns were not completely invented out of thin air. More importantly, whatever the exact timeline was, he ultimately chose to pursue and to become engaged to the close friend and roommate of the woman he had nearly married. In the scheme of things, all that matters. A man with good middos and exceptional sensitivity and integrity generally recognizes the emotional devastation that such a situation creates. Even if he believed the relationship between you and him was fully over, he still knew the history, the closeness, and pain this likely would cause. I imagine he also knew the reason you broke up with him. Yet he moved forward anyway. This is important because right now your heart is trying to simplify the story into one central idea: “If she had not interfered, we would still be together.” Perhaps that is true. But perhaps not.
Relationships that are strong enough for marriage generally survive outside opinions, rumors, and interference because both people communicate openly and directly with each other. If accusations from a third party were enough to end the relationship, then maybe there were already weaknesses beneath the surface, especially regarding trust, communication, and emotional security. That does not mean your grief is invalid. It means the story is more complicated than simply thinking she stole your future.
Now you’re considering contacting him to tell him the “truth,” but before you do, ask yourself honestly what outcome you are hoping for. Do you want him to break off the engagement? Do you want him to apologize? Do you want validation that you were manipulated? Do you want him to admit she deceived you both? Or do you simply want him to understand how deeply you were hurt? These are very different goals, and some are far more realistic than others.
What you must understand is that once two people are engaged, the frum world becomes very protective of the couple, regardless of how the engagement came to be. That said, they often become emotionally united against outside threats to the relationship. If you approach him now in a highly emotional or accusatory way, there is a serious risk that your pain will be interpreted not as heartbreak, but as jealousy. Fair or unfair, that is how these situations are frequently viewed. And there is another painful possibility you must consider: even if he acknowledges that your roommate manipulated you, it does not necessarily mean he will choose you instead. He did make the decision to get engaged to her, so as much as it hurts you to hear this, he must have deep feelings for her. I totally understand how that realization hurts you, but it is essential for protecting your dignity.
Sometimes when people are wounded, they chase not the actual person, but the imagined future they lost. You were emotionally preparing for engagement, marriage, stability, and the life you believed was unfolding before you. The abrupt loss of that dream created a kind of panic. Your mind is desperate to undo the moment when everything changed. You might be convincing yourself that if only the “truth” came out, time will reverse itself. But life rarely works that way.
If you are seeking closure, that is also often misunderstood. Many people believe closure comes from one final conversation, one confession, one explanation that suddenly makes everything make sense. In reality, closure usually comes much later, when enough time has passed that you no longer need the answers in order to breathe peacefully again.
Please do not let this experience harden you completely. One betrayal can make a person suspicious of every friendship, every shidduch, every act of concern. It can make you believe that everyone is secretly competitive and self-serving. Resist that temptation. There are loyal friends in the world. There are decent men in the world. But going forward, trust should be balanced with discernment. Never again allow another person’s certainty to override your own direct experience without deeper conversation and verification. You made a decision based on someone you trusted. That’s human nature.
As for whether you should contact him at all, if you truly feel you cannot move forward without expressing yourself, then do so calmly, briefly, and with dignity, not to win him back or destroy their engagement. Simply state your truth and release it. But understand that the most powerful response to betrayal is not chasing after the people who hurt you. It’s rebuilding yourself so completely that their choices no longer define your worth, your future, or your peace. One day, this story may no longer feel like the ending of your life, but the painful lesson that taught you to trust more wisely, love more carefully, and value yourself more deeply. n
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. Baila also produces and hosts The Definitive Rap podcast for 5townscentral.com, vinnews.com, Israel News Talk Radio, and WNEW FM 102.7 FM HD3, listenline & talklinenetwork.com. She can be reached at [email protected].
