Dear Dr. Chani,

I recently met a guy who I would like to date, but I am not sure how to proceed. The truth is we did not actually meet each other. I was out walking with a married friend of mine, and two guys walked by. One of them knew my friend, so he stopped to say hello. During their two-minute conversation, I had a good vibe from the second guy, although we didn’t speak to each other. After we continued walking, I asked my friend if she knew the second guy. She said she knew both guys but didn’t think that either was right for me. I pressed her for a reason why, and she said she couldn’t explain.

My instinct tells me that she doesn’t want to try to set me up with the guy I want to date because she thinks he wouldn’t be interested. I’m kind of insulted. Since she is my good friend, I would have expected her to go the extra mile and advocate for me. I also do not understand why she is unwilling to suggest the idea to him. What’s the big deal if he ends up saying no?

This is not the first time I’ve found myself in this situation. In my circles, it isn’t the norm to ask a person out directly, so I rely on people to think of ideas and set me up. When I see or hear about someone who seems like what I am looking for and I try to find someone to suggest the idea, it usually goes nowhere.

I feel really hopeless and frustrated with the whole process of shidduch dating. Should I just give up and resign myself to my fate?

Dear Shevy,

You are understandably frustrated with the dating process. It sounds like you feel that in your social culture there are gatekeepers who hold the keys to your dating future. Since you rely on certain people to set you up, they are the ones who can determine whom you could possibly date. You are disappointed in your friend because you feel she is holding you back from dating someone who you feel has the potential to be good for you.

It might be helpful to think about your friend’s refusal in a different way. Imagine for a minute that you were in a different social milieu, where you could ask this guy out directly. Would you feel comfortable asking him out yourself if that was the norm? It is not easy to put yourself out there and be told no. Rejection is never easy. It can also create a feeling of awkwardness between you and the guy. As you imagine what that might feel like, think about being in your friend’s shoes. You are asking her to put herself out there on your behalf and for her to be prepared to feel awkward if the guy balks at her suggestion.

Furthermore, if she does not think this is a good match and you want her to present it as her own idea, she will be misrepresenting herself. If she knows the guy and she does not think you are what he is looking for, she will be placing both him and her in an uncomfortable situation. Also, she might relinquish her credibility with him in the future. He might not continue to trust her opinion. You might feel that if she is a true friend, she should be willing to take those risks. I understand your perspective. At the same time, it might be helpful to balance it by looking at the situation from your friend’s perspective.

This way of thinking is still based on your assumption that the reason your friend said he was not for you was that she thought that he would not be interested in you. Yet, it is equally plausible that your friend knew that the guy you asked her about has a certain problem or issue and she was protecting you from getting affected or hurt in some way. She might not have wanted to explain because she did not want to reveal to you something personal about him, but she hoped that you would trust her to act in your best interests as your good friend.

Either way, it is best for you not to pressure your friend or make her feel guilty about not setting you up. Let’s explore some alternative approaches.

So far, it sounds like you saw him and had a good feeling about him. That is a nice start, but it is worth your while to explore what is beneath the surface. You could find out more about him through mutual friends and see if he really has the qualities you are looking for. As you go through your vetting process, listen to the way people respond to your interest in him. Do they sound excited to tell you about him? Does anyone say they think that he is a good idea for you? If you find someone who sounds positive, ask that person if they would feel comfortable suggesting the idea to him. On the other hand, if people sound hesitant when you ask about him, you need to reconsider pursuing him.

In general, if you find yourself repeatedly asking others to set you up with specific people and they decline, reflect on why that might be. We all have blind spots about ourselves that other people see but we do not recognize. Rather than give up, seek a competent professional you can confide in to discuss your personal thoughts and feelings. Look for someone who can help you increase your self-awareness, build upon your strengths and deal with your challenges. You can discover new realizations about yourself, new ways of considering guys who are interested in you (rather than the other way around) and new strategies to approach dating effectively.

Regardless of how many times you have hit bumps or blocks on your dating journey, you can find a path that will lead you to success. Keep going and allow yourself the opportunity to discover the person who is waiting for you.

Wishing you much success,

Chani Maybruch is a social psychologist and relationship coach specializing in teaching emotional connection and communication skills for over two decades. She coaches individuals and couples, teaches courses on how to become a master of relationships and provides free relationship resources at chanimaybruch.com. Learn a step-by-step method to improve your ability to emotionally connect with her online course: The RELATE Technique™—Seven Steps to Emotionally Connect Through Conversation. Reach out to her at [email protected]