Accompanying your children through the maze that is dating can be a nail-biting experience. As mothers, we are caught up in a range of conflicting emotions. On the one hand, we are hopeful that our child will find their life partner and start off on their own. At the same time, we are concerned not to interfere in what is their most personal and important decision. At times, we may feel strongly that they are not thinking clearly or making poor choices and feel compelled to say something, but are afraid that this may harm trust or cause a rift. As mothers, we are expected to be an empathetic listener and act as a good sounding board, rather than proffer advice that is not always welcomed. Being a mother to a dating child requires maturity and wisdom, patience and resilience.

Hopefully, things go well. Your child meets someone, you breathe a sigh of relief and then gleefully welcome a new person into your family. But sometimes, dating gets messy. Your child may be conflicted or confused about their prospects with the person he or she is dating. You watch them torture themselves, struggling with the choice of persisting or calling it quits. Finally, after what seems like an eternity, the dating fizzles out and your child—dazed and beaten—is back on the lookout.

Your child may find they are meeting few people, and few relevant options are coming their way. Alternatively, they may find that they quickly lose interest in the people they are dating. It is painful to watch your child experience a string of rejections or dating failures, in many cases for seemingly no reason at all. Years go by, and your child appears no closer to marriage. As a mother, you wonder if there is anything you could or should do.

After watching your child go through all those ups and downs, you may believe that it would not hurt to share some home truths. You may feel that they are being too “picky” or “commitment-phobic” and would benefit by having those things pointed out to them. But you are also aware that, sadly, this kind of advice, whether true or false, is rarely accepted and often resented. Many of us take a vow of silence, opting to display saintly patience and provide unrelenting validation, keeping your views to yourself. If they blame matchmakers, dating sites and other singles, you don’t dare question those sentiments lest you appear unsympathetic. When they are gripped by self-doubt and despair, you offer vain encouragement that “there must be someone out there” and urge your child to soldier on.

Sometimes, your resolve weakens and you offer “constructive advice,” only to feel guilty when it did not result in the hoped-for success. After you are told for the umpteenth time “Mum, you don't understand ... ,” you start to think you really don’t.

Did I mention that it is tough being the mother of a dating child?

My husband, Yossi, is an expert on relationships, and together we have been blessed to see two two daughters marry. Here is what I have learned. When your child is having a hard time dating, there probably are few answers that you will have to offer. Your role is to ask the right questions.

Often, young people take time figuring out what they really need in a relationship, and if that means a few bumps along the way, that’s just “life.” But when dating is proving to be a prolonged drama, it’s time to ask some questions—really just variations of a single question.

Is Something Getting in the Way?

For many singles who are struggling to form or secure a lasting relationship, there is some internal obstacle impeding their way. They are, in some way, misreading something about themselves or the experience. That’s the bad news. The good news is that in most cases, a small amount of self-awareness is all that is needed to turn things around. It’s not necessary to change anything fundamental about the person, just to recognize what those perceptions and reactions are. With improved clarity, most singles are able to make the modest adjustments to break the cycle of failure and frustration.

Here are some common, potential problems:

  • Your child may have skewed expectations about what dating and relationships should be like. Or perhaps your child has poorly calibrated responses to the dating and relationship-building process.
  • Your child may be entirely unaware that he or she has an in-built tendency to magnify faults in a potential spouse, especially as this tendency is not manifest with regards to their other relationships. It would never occur to them to question that this could be happening. Their judgment in relation to others things is usually spot on.
  • Your child may struggle with an avoidant attachment orientation—a well-documented mindset that greatly exaggerates the normal fear associated with a life-long commitment. Your child is normally quite decisive and confident, and the notion that this could be happening seems counterintuitive.
  • Your child may be regularly conflicted about their dates, always finding something about them deeply dissatisfying; it would not occur to you that he or she has a somewhat bifurcated personality. Looking at other aspects of their life would show no real indication that they have two quite distinct aspects of their personality. This is not a problem in other aspects of their lives, and they learned to manage their complex character effectively. Only during the dating process—where he or she is being pressed to choose a single person that is going to be more suited to one side of their personality—does this flower into a full-blown crisis.

These types of issues are common in singles who are not having it easy on the dating scene. They’re not serious psychological conditions and usually they can be overcome without long-term therapy. But left to take their natural course with no intervention, these tendencies can lead to years of unnecessary heartache.

Our role as mothers is to ask this question: “Could there be something getting in the way?” Take a leaf out of the book of the biblical Joseph. He was languishing in an Egyptian jail with two of Pharaoh’s ministers when one morning he notices they are in a foul mood. Rather than give them advice, he decides instead to ask them a question: “Why are you sad today?”

Your child is smart, attractive, capable and desirable as a life partner; all this drama shouldn’t be happening. Unfortunately, though, these minor hurdles remain unexplored and unaddressed. In most cases, the challenges are not truly significant, and the suffering can be avoidable through appropriate guidance.

As a parent, the most valuable thing you can do when your child is having a hard time with dating is to ask them to consider whether there is something internal (almost certainly minor) that is tripping them up. It is often the lack of self-awareness that’s at the root of so much of the hardship, and that small dose of clarity is enough to be a real game-changer.

As parents, we may not always have the answers. But it’s vital that we have the right questions.