The Art of Playful Communication in Dating Apps

Dating, Part 1 Navigating the Dreaded (But Sometimes Needed) Dating Apps! Today we started a series on one of my favorite topics: dating. When I was in clinical practice in Philadelphia, a large proportion of my patients self-identified as single, without partner, so this was one of my favorite problems to help people with, and why I wrote the book, Intimate Connections, which included my some of my personal experiences learning about dating during my medical school days at Stanford. Our special guests include our own TEAM CBT expert, Jacob Towery, MD, who presents the free annual two-day marathon on shyness called “Finding Humans Less Scary.” He will be presenting this program at Esalen as well from September 8 – 12, 2025. Check out the September 8 - 12 shyness workshop at the beautiful and dramatic Esalen in the Big Sur! We are also joined by two wonderful young ladies: Sydney, who graduated in 2024 from University of Santa Cruz, and Sophie, who recently graduated from UC Berkely. They will give us some first-hand experiences and suggestions in the navigation of dating apps. Jacob said that after his divorce in 2012, until 2020, he went on a lot of dating apps and met nearly 200 women this way, exploring both short and long-term types of dating. He said it is sometimes difficult to figure out what someone is really looking for on an app, whereas in person it is easier. The group described the tendency to treat people as objects and ghost them when you decide you’re not interested. He recommended, instead, to treat people with dignity and care, even if you’re not romantically interested in them. He said that whether you’ve been on one or many dates, don’t just ghost someone. Instead, you can let someone down gently if you aren’t interested. For example, at the end of a first date in which you don’t find yourself attracted to the other person, you could say “I didn’t feel a spark but I enjoyed our time together. Thanks for hanging out with me.” This will make it clear to the other person you won’t be asking for another date, but in a kind way, and prevents them wondering for days if you will ask them out again. In addition, he advised that initially, don’t just text people back and forth endlessly. Instead, get into real life ASAP. Meet them for coffee or ice cream or whatever would be fun. That way you can find out whether or not there’s a spark of interest. Jacob also recommended using a recent photo of yourself. If you use an older photo of yourself, the other person may be disappointed when they meet you! Jacob recommended being honest about what your interests are, and what you are looking for. Are you just looking for casual dating? Are you only looking for something that may evolve into a long term relationship? Are you interested in having children? What are your interests or hobbies? The group discussed many topics, like is it okay for a woman to take the initiative and ask people out they are interested in? It’s easy to get overwhelmed by having too many offers, too many to select from. And the whole process can be incredibly exhausting. How do you make conversation in a way that will turn the other person on and make them interested in you? What’s the secret? How do you overcome the fear of rejection? And what if you protect yourself from the fear of rejection by hiding personal information about yourself. For example, you may think that if you didn’t really open up to the other person, their rejection will be less painful because they didn’t see your so-called “real” self. Jacob emphasized the importance of being playful and creative when dating. People really like to have fun. Being overly serious or heavy can be a turn-off. Thanks for listening today! Future topics will include how to flirt, how to change the way you think when you’re rejected, making people chase you, how to get close, and more! Rhonda, Jacob, Sydney, Sophie, and David