By Baila Sebrow

By Baila Sebrow


I’m new to dating even though it’s second time around for me. I read your column and I save your articles in case I (or one of my friends) need some advice about dating. I’ve read all kinds of stories, but nothing like what is happening in my relationship.

I have been dating a  guy for five months already. The first few times he took me out to eat in restaurants—nothing fancy or expensive, but decent places. Maybe it was a red flag (that’s what my friends say), but he would always take home the leftovers. I did think it was kind of cheap, but I let it go because we were so into each other. As time went on, he stopped picking me up for dates and would make me meet him. Since we don’t live that close to each other, it got expensive for me. Most of the time he drives me home, but sometimes he’s not in the mood, so I go home myself even though it is really late at night.

Also, he has gotten very cheap with food in another way in that we don’t go to restaurants anymore. He brings food that he cooks. I didn’t really mind it at first because he’s a good cook. But the last time, he brought one small steak and divided it between us, and he added lots of lettuce, and that creeped me out.

What’s ironic is that he always talks about how generous he was with other girlfriends. For example, he says that he used to pay for babysitters for the kids of one of one of the women he was dating, and that he bought a thousand-dollar necklace for another woman. Meanwhile, he never bought me anything in all the months we have been dating.

I did tell him how I feel, but he doesn’t really have an answer that makes me happy. What do you think about all this?


There could be lots of possibilities why treats you in ways that are disturbing to you. I will delve into some of the things that could be going on, but the entire truth of what is really happening is something that only he can confirm. What I find troubling about this relationship is that according to what you say, you did express to him that you are bothered by the way he treats you, yet he makes no effort to change. And since the dating period is when one shows his best side, there is much left to the imagination about what his not-so-good side might be, specifically as it relates to how you believe that you ought to be treated by a man.

Before we explore dating styles, there is one thing that can never be compromised, and that is safety. How can he place you in a position of traveling home by yourself at night when you made a point of telling him that you are not OK with it? Even if you would not mind, a gentleman never places a woman in a situation that is not safe. This aspect of his indifference to your well-being is concerning. My strong recommendation is that you should not tolerate such behavior in anyone. Unless he is willing to come up with a solution or date earlier in the day, since for whatever reason he cannot drive you home, you should not continue dating him.

People have different styles when it comes to dating, and when things are mutually acceptable, the relationship coasts along with few complaints. The traditional role is that whoever issues the invite is the one who pays for the meal and should also take responsibility in the arrival and departure of the woman. So, for example, if the man invites the woman out for an evening date at what would be considered mealtime, then unless he tells her that she should eat before the date, the respectful thing for him to do would be to offer her food. Figuring out how she gets to the destination should also be his concern.

As the relationship progresses, and people get more comfortable with one another, formality typically relaxes, and there is nothing wrong when the man does not consistently pay for restaurant meals, particularly if the couple gets together several times a week. In fact, married people do not go out to eat every day either. It is possible that the guy you are dating may be having financial issues, and although he spent money on restaurants early in the relationship, now that he feels at ease with you, he might think you won’t mind if he does his own cooking for the date. If his financial situation is the problem, you will have to decide whether you are able to handle whatever is going on in his life. However, if it turns out that frugality is the reason, this is the lifestyle you will have to become accustomed to living should you marry him one day.

I am wondering about the gifts that he has bestowed on his previous relationships—paying for babysitters and a pricey necklace. Why is he even sharing this information with you when he has no intention of doing anything similar for you? If his finances have changed since those periods in his life, telling you what he did for other women is insensitive and hurtful. You must be feeling as though he is taking advantage of your time, even if he might be giving you indication that he wants a future with you. Actions do speak louder than words. And besides, gifts do not have to be expensive. There are less costly gifts than thousand-dollar necklaces to show that he is thinking about you. So this follows along the same lines of his apathy about your safety. Based on what you are describing, this does not sound like a healthy relationship. The question is if you really want to work with him on this relationship, despite the issues that you are disclosing.

If the answer is yes, then I advise you to sit down with this guy for a serious discussion, not hit-and-run type of comments that you might have tried previously, which did not get you anywhere satisfying. Before you talk to him, make a list of all the things that are of major concern to you, and come up with a few options of solutions to each of them. I will help guide you based on what you have mentioned.

If going out to a restaurant is important to you, and he cannot or does not want to finance it, then if you don’t mind splitting the check, suggest that to him. Or maybe you can offer to bring sandwiches or cook something for him every so often. This relationship does not sound brand-new, so it is reasonable to make such offers. Again, this has to be something about which you are fully agreeable, and you should never feel that it is a pressure of any sort. Nobody is forcing you to remain in a relationship with him. You always have the option of saying that this does not work for you.

People in exclusive relationships want to feel special. It is fair to expect a little something occasionally from your significant other. Tell him in clear terms that you would appreciate that from him. If he comes up with reasons why he cannot or will not do that for you, then you will know exactly what you are dealing with. I have a hunch he will not refuse, but do not expect anything expensive. It sounds like you care enough about him to accept that it is the thought that counts. It would also be a good idea for you to reciprocate and to pick up an inexpensive trinket once in a while, too. Showing care works both ways.

I will conclude my response to you by reiterating the safety factor that concerns me, and I will tell you that lately this has come to be considered normal in frum dating. There are men for whom it has become the accepted mode of behavior that the woman needs to find her own way back and forth. I will never agree with that concept. (The only exception is if the date is arranged for an afternoon and will end while it is still daylight.) It does not matter if the woman is driving her own car, relies on public transportation, or takes an Uber. Traveling home alone late at night can place a woman in harm’s way. No decent man would insist on that. It demonstrates a lack of concern and respect for another human being, and such a person is not capable of being a selfless, devoted spouse. That said, tell him that you are willing to meet him during the day if he cannot personally see you home safely, and that there is no room for debate on this issue. 

Kindness, sensitivity, compassion, respect, and decency are never negotiable in any type of relationship, and no person should ever feel compelled to make concessions in those areas just to not be alone. It is better to be alone than to feel lonely while being with someone.

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 Read more of Baila Sebrow’s articles at


Please enter your comment!
Please enter your name here