Dear Matchmaker: Harassing behavior, photo shoots & multiple setups

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Virtual relationships, online dating and social networking concept - woman sending kisses with computer monitor (photo credit: INGIMAGE)
Virtual relationships, online dating and social networking concept - woman sending kisses with computer monitor
(photo credit: INGIMAGE)
Navigating the dating world can be exciting, but it can also be frustrating and confusing. Who can I turn to with my questions? How do I handle different situations? How can I put my best foot forward? There are so many questions. We hope to be able to help you with the answers and provide guidance on how to navigate situations that confuse YOU.
We welcome you to submit your questions about dating, online profiles, dating etiquette, relationships and more. Real matchmakers will answer your questions, providing their perspectives (which may sometimes differ greatly) on the dating process.
Dear Matchmaker,
I went on what I thought was a nice date with someone and she said she enjoyed it too. But since then I’ve been trying to text her, and she hasn’t responded. I must have sent her 15 messages in the last week, but nothing. How do I get her to answer me?
Confused in Jerusalem
Dear Confused in Jerusalem,
You don’t. Fifteen texts... wow. Just stop. People say things to be polite sometimes. Your over-eagerness or certainty may have caused her to lie in the first place – she didn’t want to burst your bubble in your face. And asking “how do I get her to... ” tells me you should stop dating and get some social skills training. You clearly don’t understand relationships.
– Rabbi Yisroel Bernath, known as “The Love Rabbi,” has extensive experience with counseling couples. Starring in the CBC documentary Kosher Love, he is a matchmaker with and founder of
It sounds like she didn’t have the heart to tell you that she did not want to continue. Do not try to contact her again and move on.
– Chana Glikin is based in Minneapolis but works with Lubavitch and hassidic singles around the world. She dedicates countless hours as a matchmaker with
I think she has answered you already, she is not interested. Plus, even if she was interested, she does not have good middot (character traits). A nice girl with good manners would have said, on the first text, you are a very nice guy but not for me. A nice girl would NEVER ignore your 15 texts. I would get her out of your head and move on.
– Dr. Tova Weinberg has been making matches for 40 years and is the founding matchmaker on She has over 300 marriages to her credit.
Dear Matchmaker,
I am putting up a profile on an online dating site. Someone told me I need to get formal pictures from a photo shoot. What if the formal pictures don’t represent the real me? Isn’t it better to be me?
Chaya, New York
Dear Chaya,
I hear your argument with regard to uploading photographs to online dating sites. And when you scroll through profiles there can be a wide range of photographs from elaborate photo shoots to selfies. How do we determine which photographs are going to present the most authentic version of ourselves?
Whether we agree with the reasoning or not, when we scroll through profiles, it is the photograph that is more likely to determine whether we continue to look at the profile. After all, your profile on your dating site is your product, your marketing tool, the only hard copy of you that you can offer to the virtual population perusing the site. And for that reason, every aspect of the profile should be fresh, current, dynamic and attractive. Including the photograph, which should shine and radiate above the rest.
Once your profile has been approved by the man, then you are correct in claiming that when you meet in person, you do not want the man to think you have misrepresented yourself. But although photo shoots are elaborate and may not be a living representation of you when you meet, they are still you. Just a different representation of yourself.
Dating sites also have space for more than one photo. You may want to keep the main photograph for the photo shoot and the second or third photo to show yourself in your more regular attire. This will show the diversity of you as a person, someone who enjoys getting dressed up as well as a person who can enjoy chilling in jeans and a T-shirt.
A formal picture from a photo shoot may also help in attracting a like-minded man who also took the time to invest in making his profile look above the average. Rather than see it is a misleading addition to your profile, see it is an asset, and one that may pay dividends.
– Suzi Zettel has a master’s degree in social work and has been a matchmaker on and for over 15 years.
I know that the idea of taking pictures for dating is so frustrating and demoralizing. But there was an interesting article in The New York Times a few years ago, when Tinder was launched, about the science behind the app and what you can really learn about someone from a picture that would make you to want to go on a date based on a picture alone. For example, if you saw a picture of someone with a dog and you hate pets, you would probably not want to go out with that person. If you saw a picture of someone outdoors in the warm sunshine smiling and happy, you would probably feel drawn to the general happiness of the photo but you might react differently to a photo of someone in a dark setting who was not smiling.
I would suggest taking pictures that represent the best version of you. Nowadays people have access to so many photo-taking tools on smart phones, portrait mode, filters etc. So many people make their photos look like they’re professionally done, you may as well too. This does not mean you need to put on the gown you wore to your sister’s wedding. You can do this in normal clothing.
Just think about lighting, outdoor lighting or at least lighting where you have light on your face opposed to your eyes being in the dark. Also, think about what you can do in the photo to represent you. If you love volunteering with kids, then make take a picture doing that, if you love the beach, maybe take a picture walking in the sand.
But also, and equally important, think about that time you saw a really cute guy when you were just running to the market and you regretted leaving the house in your pajamas without brushing your hair because he didn’t even notice you when you smiled and waved. Put yourself together the way you would want to look when you run into that cute guy again.
– Lori Salkin is a dating coach who focuses on the needs of traditional to Orthodox clients. She volunteers as a matchmaker on and maintains a dating advice blog The Matchmaker Diaries.
Dear Matchmaker,
I have agreed to go out with someone, but I haven’t heard from him yet. And now someone else is looking to set me up with someone else. Should I accept both setups?
Abby, Toronto
Dear Abby,
I would be very interested to know just how long you have been waiting for the first man to call. If we are only talking about a day or two, it would seem ethical and correct to wait at least another day or two, as after all, you did make an agreement.
I estimate that an average and reasonable time to wait for a call is around three days. After that, it is unreasonable to think that you are going to hang around and wait until he is finally ready to call. If you have a matchmaker or friend who can act as a go-between, you might be able to find out his exact intentions with regard to the match. Then it will be easier for you to know how to proceed.
If you cannot get hold of this man and the match is dragging on, I would recommend accepting the second match. If the second man responds right away, and you set a date to meet, at least you are on the right path. Should the first man subsequently get back to you with apologies and excuses and still want to meet, put him on hold. The first man who responds will probably prove to be the most reliable and dependable, which are two very important, if not crucial, aspects of a relationship.
The dating world requires direct and clear communication, including prompt replies even if they are to apologize for delaying a date due to unforeseen circumstances. Each person who is involved in a “set-up” needs to approach the prospective date with an ethical mindset, and remember that no matter how burned out or overwhelmed you may be from an endless stream of bad dates, you need to treat the person you have been set up with in a courteous and respectful manner.
Dating is hard enough without having to be kept waiting for the second party to respond. A person who disregards the importance of prompt, clear and direct communication can actually disrupt the equilibrium of this delicate dating world!
Now it is up to you to make sure that your intentions are just and considerate for both men concerned! I wish you the best of luck.
– Suzi Zettel
I get this question every single day!
It’s so frustrating to go weeks at a time in a dating drought and then to feel like everyone wants to go out with you at the same time, and then if you turn one down, of course, this one will be a one-and-done when he finally gets back to you, and the other person will be busy with someone else by then. It is also so frustrating when you only take one at a time and it can take two weeks to set up that one date.
I always say, do whatever you feel comfortable with. There are as many people who take multiple first and second dates at a time as there are those who only date one person at a time.
If you do date multiple people at once, just be careful to focus on each one and make sure you give each a full chance, and narrow it down to one person as quickly as you can.
– Lori Salkin 
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The writer is a professional matchmaker, coaching matchmakers from a variety of organizations.