By Baila Sebrow



I don’t see it, but I am told that I am a “handsome young man” by all the ladies who meet me — except the ones that I date. I struggle with finding a girl. I am an only child born to much older parents, and they are not at all connected to anyone who can help me. Their friends have grandchildren almost my age, so they are of no help to me either. As you can imagine, getting dates does not come easily to me.

When a girl finally agrees to go out with me, the answer is always the same: “Nice guy but not for me.” When I try to find out what it is exactly that they don’t like about me, they never tell me. I wish I knew so that I could work on it and maybe improve myself. But if they don’t tell me, how can I fix what I don’t know about?

I know that I am not a “cool guy” and I get along best with girls who are not cool, but even those girls don’t like me. So how can I get a girl to go crazy over me, and where should I go to meet such a girl?


If you are looking for someone to wave a magic wand and you will suddenly be transformed into a Don Juan, there is no such thing. And I will share something else with you: no man has every girl go crazy over him, in the same way that no girl has every guy crazy over her. That’s not how these things work.

Whether it is physical, emotional, or spiritual, what attracts one to another varies from person to person. And that’s not just in romantic situations, but in friendships, too. Oftentimes, there is no rhyme or reason why you feel an attraction or a connection to someone and not to another. And you cannot force it or make it happen either.

There is no mention about your age, other than that you are a “young man.” That doesn’t tell me much, because age is relative. I sense your desperation to find somebody who will love you and whom you will love. That is a basic human need. What I think might be going on here is that the type of girl you would like to meet and form a relationship with does not seem to work for you. When people first start to date, they form an image in their mind about the person they hope to marry one day. If it materializes exactly to their specifications, that’s great. However, in many cases it doesn’t; hence, all the unhappily single people in our midst.

You make mention of the fact that you are not “cool,” but do you realize that it is a particular type of girl who seeks that “cool” guy? And if you are on the quiet or reserved side, why are you looking for the girl who makes it clear that she seeks a man who is the opposite of you?

There is nothing wrong with being the way you are and who you are, and there is also no reason to change that aspect about yourself. Not everyone can be the life of the party, and not everyone even wants to be around such a person.

Your problem is not that you are not cool enough. I think your biggest problem is that you are not in the right circles to meet the type of girl who will one day “go crazy” over you. You say that your parents are older people, so it stands to reason that they are completely unfamiliar with how to assist or even advise you. Dating in their days was vastly different than it is today.

I wonder what type of community you live in. Are there enough young people similar to you, or have your parents settled and remained in the same place since their youth? That makes a huge difference. If you live in an area where the people are much older, then your social life is limited and you are relying on meeting girls whenever you get introduced to someone or if you happen to meet them by chance. That said, your options thus far are narrow. Again, I don’t know where you are holding in other areas of your life regarding your age and if you are working and able to support yourself by moving on your own to a different city or neighborhood. And even if you do, you might still be facing the same problem if you are looking for something that may not be available to you.

Though not always the case, people who are more on the reserved side tend to spend a lot of time to think things through carefully. In light of your situation, that will serve to benefit you now. When singles experience challenges in dating, and they sincerely seek a solution rather than just vent and complain, here is what I recommend.

I don’t know how introspective you are. If you feel you can do this on your own, that’s fine. However, it still wouldn’t hurt to reach out to somebody to assist you with the following exercise. Take three sheets of paper and number them. On the first sheet, write down all the qualities you seek in the type of girl you feel will make you happy. On the second sheet of paper, write the names of the girls you had dated, but who then rejected you. On the third sheet of paper you will write the names of the girls you rejected (yes, I do believe you have done your share of rejecting, too!). After you finish, study sheets number one and two carefully. I predict that of the girls who declined you, you will discover that at least many, if not most, in retrospect, would not have worked out for you in the long run. Now, for the last part of this exercise, take the last sheet and study the names of the girls you declined and try to remember why you made that decision. Whatever your reasons may have been at the time, if it happened a while ago, it would not surprise me if you discover here that perhaps your decision may have been made too hastily, and that at least one of the girls should have been given more of a chance.

After you complete the exercise, I believe that you will have more clarity about the type of girl you should be looking for. At that point, you will be ready to reevaluate your priorities. This will be the time to reach out to matchmakers and meet with them to explain who you are, where you are coming from, and what you seek in a potential spouse.

Getting that first date is only half the objective, as it appears that’s where you previously failed most. Let’s talk a bit about the impression you make on your dates. Before leaving your home to go on a date, take a long look in the mirror and ask yourself, “Would I want to be seen on a date with this person?” If you are not sure of the answer, ask someone for an opinion and listen so that you are certain that you are appropriately put together for a date.

Once you have already met the girl, there is dating etiquette that applies to all ages and hashkafahs. Be chivalrous by opening the door and allowing your date to walk ahead. Do not monopolize the conversation with stories about your life. People do that sometimes because they are nervous, but it can easily bore somebody. If the girl is not too talkative, ask her questions about herself. That shows interest in wanting to get to know the person you are with on a date. There is also nothing wrong with complimenting someone on an accomplishment or perhaps even on a piece of jewelry. I know that in some circles that is considered a faux pas, but an appropriate and sincere compliment will make you appear genuine and kind.

Whatever you talk about while on the date, please do not complain about anything in your life. Nobody wants to be around a complainer or a negative person. It’s also a good idea to familiarize yourself ahead of time with what the girl does with her days—school or work—and try to come up with something to say or ask about it beforehand. Also, a trick that many motivational speakers use to immediately ingratiate themselves to the listening audience is to tell a suitable joke where it doesn’t take too long to get to the punchline. It helps to put people at ease and in a good mood.

The ideas that I am giving you are only tips to get your foot in the door, so to speak. Ultimately, you need to be yourself, and you will, b’ezras Hashem, meet the girl who will recognize your qualities and the value you bring to her life.

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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