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Overcoming “Dating Despair”

By Gabriella Aratow


If there’s one thing I’ve learned in my years working with singles as a professional matchmaker, and being single, it’s that dating can sure get people down. I don’t know if there’s anyone looking for love who doesn’t sometimes go through what I call “dating despair.” We can feel angry about those who mistreated us as we sought connection and confused as to why others land what appears to be a perfect love story when we did not. Who wouldn’t be frustrated by the ineffectual actions of others, and hurt by the rejections, and scared about how bleak a solitary future may become?

A four-part process to empowerment

Gabrilla Aratow a professional matchmakerSingle people can also be ashamed of ways we may think we failed to achieve a normal life, so we’re not only handling the challenges we go through emotionally (and, by definition, lacking a partner to support us) but also carrying a concern about how we may appear as mis-wired misfits. Do you recognize this spinning wheel of negative notions? Are you exhausted by the seemingly inescapable repetition of it all? Then you have stepped through the door of dating despair. Here’s the thing: The very fact that I can call this cluster by name should tell you something—it’s normal. Yes, it’s natural to work yourself into this dark place about your romantic predicament. You’re human. Ultimately, no matter what happens in one’s dating life, we serve ourselves to find the upside in our struggle. With the preciousness of each day your inner being wants to be expanding your sense of equanimity, not depravity. I’ve observed that dating can be the very process by which we come to higher levels of self-actualization and fulfill on our ability to uplift not only ourselves but others. With my clients I do a four-part process I developed to move them out of dating despair and to empowerment. It’s modeled on the functions of the four chambers of the heart. My program is extensive, featuring explanations, stories, and dozens of exercises. But here is a mini version, a quick formula, if right now you need to pull yourself out of an abyss.



Since in the first chamber of the heart blood enters depleted of oxygen. In this opening action of my method my clients face what caused their despair. Break-ups? Discrimination? Fraudulence? We acknowledge these things arise and we take inventory of the ways we got cut down. One exercise from this chamber I call “Share the Solution.” Picture yourself breathing IN all your despondency, then envision your body as a container of transformation in which pain morphs to calmness. Now breathe OUT the new energy, giving it to the world.


The second chamber of the heart sends depleted blood to the body to gather oxygen. In my program, it’s where we ready ourselves to date again. Internally, we examine ways our narratives have gotten stuck and nudge ourselves away from victim-hood. Externally, we polish our presentation. For exercises here, pick three of these five internal shifts: 1) See stand-up comedy or anything that makes you laugh. 2)
Spend time catching up with your most content friends. 3) Visit an art museum. 4) Volunteer at a charity. 5) Exercise in nature. Then pick three of these external shifts: 1) Ask a stylish friend to re-organize your wardrobe. 2) Deep clean your home. 3) Update your haircut. 4) Have your teeth whitened. 5) Follow the ‘Whole 30’ eating program for a month.


Where the heart receives back newly-revitalized blood. In my process we focus on self-examination as we start to date, viewing ourselves under the inquiry of showing up with wonder. We examine if our behavior is coming from wounds or organic spontaneity. Begin a dating journal. Take 30 minutes after a date to ask yourself: Did you say or do anything you regretted? Why? Was anything said that made you feel inadequate? Can you trace those feelings back? Did you sense yourself as closed or open in the person’s presence? Were you having thoughts different from what you were outwardly projecting? What prevented you from being vocal about your truth? What could help you achieve what you want to be different on your next date?


This chamber pumps out re-oxygenated blood to nourish the whole body. In your fresh mental space here you discover the power you hold to uplift others, no matter the outcome of the dates. What becomes important is the strength you possess in how you impact people, even if it’s only in a 45 minute exchange. At last, you claim agency for your dating life as a method to intentionally support the value within yourself and all humanity. At this point you are ready for the “Complete Date” exercise. Create a personal vision for the Utopian world in which you long to live, and develop pre- and post-date mantras that allow your dates to exist as entities supporting your vision. I hope this method has been of help to you.



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