When Love Feels Hard: Compassionate Conversations for the Dating Journey

Dating can be brutal. The process alone is enough to break even the strongest of us. But it’s the letdown, time and time again, that serves as the dominant narrative in the lives of so many. These ongoing perceived failures often serve to reinforce one’s own lack of self-confidence. Furthermore, it impacts energy levels during dating and one’s investment into dating itself. Unfortunately, it creates the perfect storm that can lead to self-fulfilling prophecies and real obstacles in the dating process.

As with all healthy communication, the articulation of ideas and emotions is essential for better understanding and effective problem solving.[i] While this might sound basic to some, it is anything but. I always share with clients and those who confer with me about particular relationship issues, that the clearer things are expressed in relationships, the less ambiguity there is and ultimately the better the prospects are for working through issues together. To this end, we need to address an issue that is both real and debilitating in the lives of so many. I am speaking about dating apathy, or more specifically, the relentless cycle of disappointment in dating that results in a numbing sense of indifference, where individuals become emotionally detached and less invested in the process, ultimately hindering their ability to form meaningful connections or even have the will to start the process from scratch each time.

To be clear, the purpose of articulating the issue is as important as the solutions I will provide. The first step to all healthy resolutions is a clear understanding of the presenting problem. The problems here are an outgrowth of the specific negative experiences throughout the dating process.  I would like to outline the three major contributors to dating apathy and how we can work to deal with them effectively, offering a new lease on relationship prospects with energy and vigor, albeit cautious optimism.

1. Lack of self-confidence and self-worth
2. Emotional exhaustion and burnout
3. Fear of vulnerability

Dating is fraught with a whole slew of potential negative ramifications when it is “unsuccessful”. Repeated rejection and unmet expectations (either due to unrealistic expectations or unmanaged expectations) can wear away at a person’s self-confidence thereby positioning itself as the dominant narrative in a story of perceived inadequacy.[ii] This will impact on the way a person approaches future dates in general and more specifically it may create disengagement or defensiveness. It may also cause overthinking, which can diminish one’s ability to be emotionally available thus negatively affecting a person’s ability to build a genuine connection.[iii]

Any solution must look to reinforce self-esteem and promote an attitude that encourages moving forward and embracing the future with confidence.  One way to do this is through self-reflection, self-compassion and self-acceptance. I would like to draw the readers attention to the fact that each facet of the solution for the aforementioned challenge includes the word “self”. The reason for this is because the negation of oneself due to self-criticism is detrimental to growth.[iv] Emerging from difficult situations unscathed and undeterred is virtually impossible. However, evolving from tough places while remaining healthy and intact builds strength and resolve, not to mention the drive to continue pursuing one’s respective goal. Techniques that have been found to be effective, utilize strategies that promote self-awareness and self-compassion, such as mindfulness or journaling. Reframing negative thoughts is also highly effective by way of recognizing that rejection doesn’t define personal worth.[v] Another path that can be highly effective in impacting and helping to reinforce self-esteem is by focusing on one’s own personal growth. Investing time in developing skills, interests, and emotional resilience will help to ensure that we are more fulfilled and confident outside of dating. This in turn makes it easier to approach dating from a place of strength and self-confidence.

It is crucial to remember that we are more than the dates we go on and the success of those said dates! The most terrible thing for me to hear is when someone asks “what’s wrong” with a specific person due to his or her lack of success in dating. As if to say that success in dating or lack thereof, is an indication of some sort of deficiency in the individual. There are plenty of people with inadequacies both successful in dating and not! On the flip side, fully functional and successful people may struggle in the dating process, and it is not an indication of something sinister. It usually just requires a little work, encouragement, reframing and some skill learning and building. Sometimes, it may require reframing negative patterns, especially if past rejection triggers deeper issues around self-worth. It certainly should not be an open door for judgmental comments or skewed thinking due to a limited understanding of the underpinnings of theories in building and maintaining healthy relationships.

In addition to multiple breakups or general dating woes becoming a source of negative self-perception and a lack of self-confidence, they also lead to another significant issue that I am increasingly observing in my practice and more broadly, namely emotional exhaustion and burnout in the dating process. Dating can be an emotionally draining process, especially when there’s a familiar cycle of hope and disappointment. This exhaustion can lead to a lack of investment in the process, creating apathy and disengagement. Setting up healthy boundaries can be an effective way of dealing with this ennui. It gives room for a person who is feeling overwhelmed, to take breaks when necessary and get the small emotional recharge that they may need. The key, I believe, is to date with a sense of balance as opposed to a sense of urgency.

Another important technique to avoid “burnout” and the accompanying lethargy is to appreciate the time spent getting to know new people. Nowhere does it say that one is not allowed to enjoy having a conversation with someone, even if it doesn’t lead to marriage. The idea is that if one dates with the intention of appreciating the experience, the date no longer feels like a task or a burden, but rather an exciting new opportunity. For all the naysayers who are thinking in their heads, easier said than done, I would say that while it can definitely feel discouraging after dating for a while without seeing the results one wants, the key is to keep shifting the focus from the outcome to the experience.

Lastly, one of the cornerstone facets to healthy relationships is the ability to be emotionally vulnerable.[vi] Without this, it becomes extremely difficult for people to connect on a level that fosters trust and safety. These are necessary components to everything from healthy communication to conflict resolution.  However, as dating trudges on and there are continued disappointments or a well-founded fear of future rejection, it can lead to emotional guardedness. The fear of showing one’s true self or being emotionally vulnerable can sabotage potential connections, leading to superficial engagements or creating an invisible wall between oneself and potential partners. The unfortunate consequence is an inability to form healthy and meaningful connections. This lonely cycle feeds on itself and sucks in family and friends with astonishing speed. As people begin to reinforce one another’s frustrations, things are seen in the context of the presented situation and without an eye toward the future.

There are times that emotional vulnerability needs to be practiced and relearned, especially in the event that there has been some sort of emotional injury due to a potentially difficult breakup. This can be done with friends and family whom one can trust. This way there can be small incremental steps to build confidence and share feelings and thoughts. It breaks the stigma, if you will, and allows one to reacquaint themselves with the fear and discomfort of being vulnerable. However, like all vulnerabilities, the more people gradually practice expressing their true selves, the more they build the fortitude to reenter the dating scene. This is important because vulnerability is not just a strength in a relationship, it is essential for deeper connections, meaningful relationships, and effective communication. When individuals embrace vulnerability, they create space for authenticity, trust, and emotional intimacy to flourish.

One of the ways to relearn emotional vulnerability is by engaging in conversations that promote emotional connection rather than just surface-level exchanges. Asking questions and sharing personal insights helps to build trust and can lead to meaningful relationships. I would not suggest that this be stage one of the dating process. Trying to create an emotional connection too early in the courtship process will undoubtedly lead to emotional confusion and a more complicated path forward.

In my practice I have developed a much more streamlined dating process, based on research and experience that takes the emotionality out of dating when it is too early on. Rather, the focus should be on identifying objective standards in the beginning. This creates the necessary foundation upon which it is easier to create trust, safety and ultimately emotional vulnerability. This being said, emotional vulnerability is as fragile as it is essential and people who have been dating for a while with little success may resort to self-protecting. This needs to be respected and validated. At the same time, it needs to be understood in context whereby it is possible to navigate these emotions in a healthier way and not serve as a catalyst for emotional paralysis. Once this happens, dating can move forward with confidence, creating a more positive and fulfilling experience.

One powerful technique I love using with my clients to help them reframe potential risks with a more proactive mindset is the “If-Then” reframe. This approach encourages individuals to complete a sentence that presents a vulnerable situation while also identifying a positive resolution, even if things don’t go as planned. For example: “If I share my feelings and it doesn’t go well, then I can still be okay by _______.” This reframe creates a built-in safety net, reinforcing the idea that they can handle discomfort and navigate challenges with resilience. This shift helps to reframe vulnerability as a risk that can be dealt with rather than a danger, allowing them to open up with greater confidence. Ultimately, the fear of vulnerability is real and potentially debilitating, but it is an essential facet to the development of healthy relationships.

Each of these issues is rooted in fear and the emotional weight of past experiences. This is not to be taken for granted as it can weigh heavy on individuals. As with all concerns, there needs to be validation and for each person to feel safe to share without being nervous about being judged. However, by addressing these issues with a proactive and mindful approach, it is possible to shift the narrative and approach dating with a healthier mindset, fostering genuine connections that align with one’s authentic self. This shift enables wounded daters to transform future dating experiences into ones filled with excitement and hope.

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[i] Salovey, P., & Mayer, J. D. (1990). Emotional Intelligence. Imagination, Cognition and Personality, 9(3), 185-211

[ii] Pelcovitz, D., & Pelcovitz, E. (2016). Life in the Balance: Torah Perspectives on Positive Psychology. Maggid Books.

[iii] Nolen-Hoeksema, S. (2000). The role of rumination in depressive disorders and mixed anxiety/depressive symptoms. Journal of Abnormal Psychology, 109(3), 504-511.

[iv] Muris P., & Otgaar, H. (2023) Self-Esteem and Self-Compassion: A Narrative Review and Meta-Analysis on Their Links to Psychological Problems and Well-Being. Psychology Research and Behavior Management,16, 2961-2975.

[v] Leary, M. R., & Baumeister, R. F. (2000). The nature and function of self-esteem: Sociometer theory. In M. P. Zanna (Ed.), Advances in experimental social psychology, Vol. 32, pp. 1–62

[vi] Gottman, J. M., & Silver, N. (2015). The Seven Principles for Making Marriage Work: A Practical Guide from the Country’s Foremost Relationship Expert. Harmony Books.