I started dating someone about two months ago and he recently brought up a touchy subject that has me questioning. I’m in my last year of medical school and he’s been working for the past five to six years. He’s about six years older than me. The past two months have been great. He’s been reliable, attentive, and consistent in his communication. He recently brought up the subject of how I’m paying for medical school, whether student loans or my parents, and he asked for specific amounts. These questions made me uncomfortable and felt invasive because we are still in the early stages of our relationship, still getting to know each other, and finances is a loaded discussion.

Around the same time, I’ve opened up to him about some insecurities I have regarding my physical appearance, and I mentioned going for consultations regarding plastic surgery. As expected, these procedures can be costly. He was taken aback by this because he didn’t consider me the type of person to get cosmetic surgery when the cost of education is so high. He felt it was indulgent and also financially irresponsible to pay for both, and he insinuated that my values were not in line with his. He expressed concern that my values regarding money reflect a certain financial irresponsibility that can affect a marriage.

He is now seriously questioning whether we should continue to see each other. I tried to clarify that I confided in him from a place of vulnerability, and the consultations were merely a fact-checking measure to get a better idea about price, not necessarily to schedule the procedure. I told him I take my student debt very seriously and I wouldn’t make an irresponsible decision given the situation I’m in.

He left me feeling hurt and confused, questioning my decisions about my own life, and reeling because he judged me so harshly. I told him that he was jumping the gun about the relationship by asking so many detailed questions regarding finances, and that we were not up to that discussion yet. While he did apologize for criticizing me and making me feel uncomfortable by asking such personal questions, the truth is, I’m not sure I want to be married to such a critical, judgmental, controlling person.

In addition, I suspect he was trying to fast-track vetting me out for marriage by asking loaded questions early on, seeing if I had healthy boundaries or not, and making misguided assumptions about me. The fact that he put so much weight on these misguided assumptions is concerning to me, especially in a long-term partner. No relationship is without problems or conflicts, but I’m not sure if this is a problem that can or should be worked through. What do you think?


Let me phrase it to you like this: All unhealthy relationships have problems. In fact, not only do these problems remain and fester, they get worse over time, and the pile of problems grows and grows until it becomes a veritable mountain. This is the typical scenario of a toxic relationship. In contrast to a healthy relationship where both partners support each other in life decisions, the problems and challenges they do encounter are resolved because both parties are willing to do the work and make it successful. At this juncture, you must ascertain if the relationship you are in is healthy enough to work towards a resolution, or if it a ticking time bomb.

In almost every conflict that arises between a couple, it is always their prior history that comes into play. That’s why I always stress to single men and women that before they get involved with someone, they do a thorough research into that person’s background. That doesn’t mean you should call every Tom, Dick, and Harry and gossip with them about that person and his/her family. It means you should listen to what the person is saying during the crucial first two to three meetings. You get lots of information that way, particularly their dating history, manipulating tendencies, and how they view finances. This is the period where it is mandatory to take apart every sentence they say that sticks out in your mind, but it is also when you are emotionally still able to do so.

Once you get infatuated with a person, you are emotionally entrenched and it is usually way too late to make an educated decision. At this juncture, the question you need to ask yourself is: Does this relationship involve open communication, trust, honesty, and respect? Additionally, is this guy the type of person who would be willing to compromise, or is he a “my way or the highway” type of person?

Here are my concerns. Though you say that his communication and attentiveness were great, that doesn’t seem to be the case anymore. The moment you start second-guessing somebody’s intentions or actions, that demonstrates a lack of trust. His second guessing of your ability to manage finances or hinting at your ability to be economically responsible demonstrates a lack of trust. The aspect of trust is now missing from your relationship. Not only that, but based on what you are saying, you feel that there is a miscommunication between how he views you and the way you truly are. That said, there is poor communication between the two of you, and I don’t think it has anything to do with the way you are expressing yourself. Rather, he chooses to see things his way and judge people harshly who live another way. That tells you that you are no longer equal partners in the relationship.

Moreover, he doesn’t respect what is important to you, so how can you even begin to think you can be yourself with him? You can no longer have the normal fun that comes with dating somebody, the spontaneity that comes from enjoying yourself in this type of setting. You will always be guarded and cautious, afraid of his wrath. This relationship as it stands now has all the future makings of causing you to feel like you are constantly walking on eggshells. There are unfortunate cases in marriage where a woman wants to purchase something that is important to her or the family, and she must do it behind her husband’s back because he will either forbid her from buying it or give her a hard time if she does. That’s a tragic way to live.

If you are thinking that I’m being overly cautious about your well-being in the relationship, just look at his detailed line of questioning concerning your wanting to finance a cosmetic procedure. It is none of his business. He does not have the license to be taken aback by any cosmetic procedure you think you need, nor does he have the right to judge you. It is impertinent. Nor should you have been in the position where you had to defend your vulnerabilities because he is not entitled to that. You are not yet husband and wife. You do not have a ring on your finger that gives him any sort of carte blanche to become your money manager. It does not sound like you are expecting him to pay for your luxuries and debts, so in layman’s terms, he is being controlling and nosy.

You are correct to think he is trying to fast track vetting you for marriage. Going even deeper into that possibility is that he might be looking for a reason to nix the possibility of committing to you by creating a false narrative about you. And if you need proof of that, you said so in your own words, “He already stated that he felt that my values are not in line with his.” He further cemented his comment when he expressed concern that your mentality about money reflects a certain financial irresponsibility on your part. Do you really think that if he is so fixated on that opinion, that you will somehow magically make that disappear from his brain? This is commonly seen when a person who is looking for a way out of a relationship creates a “problem” (real or perceived) with the other person’s character. Do you need more proof? You wrote: “He is now seriously questioning whether we should continue to see each other.”

I am not impressed with his apology for criticizing you and making you feel uncomfortable. He still wants to conduct himself as a gentleman, and whether he was right or wrong according to his perception, he did not want to leave you feeling that he was the bad guy here. I am sorry to say that based on all the information you shared, he will one day exit the relationship, maintaining the excuse that as wonderful a lady as you are, you are both at different places in life.

So, where do you go from here? You are undoubtedly rewinding your mind back to the early days of dating, when everything was rosy. Erase those thoughts. Early dating is rarely the true depiction of an individual. His true character is on full display at the present and reflects who he genuinely is. That is the real him. Can you live with that?


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,, Israel News Talk Radio, and WNEW FM 102.7, FM HD3, listenline, & She can be reached at


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