In the Dating World, Crafting the Perfect Message Is Its Own Art Form

Ms. Wonderlin, who had been offering dating courses since fall 2021 but began catering specifically to texting issues starting in September, is one of the multiple dating coaches attempting to provide clients with the written communication skills necessary to take matches offline and into the real world — and then keep them going. Among the questions they attempt to help their clients answer: What’s a great first message to send on a dating app? How do you flirt in a way that’s not too creepy? What if they simply don’t respond?

With almost 180,000 Instagram followers, Blaine Anderson, a dating coach in Austin, Texas, has always found that her videos about texting have been a hit with her mostly male audience. This, in addition to her personal experiences receiving weird or too many messages on dating apps, inspired her to launch a course called Texting Operating System in August, “to eliminate guys’ stress and anxiety from communicating with women via messages or text,” Ms. Anderson, 33, said.

According to Damona Hoffman, a dating coach based in Los Angeles and New York and a host of the Dates & Mates Podcast, many people get stuck in what she calls “textationships.” Texting has become its own phase of dating, she said, and her program, “Healthy Communication and the Texting Trap,” which costs $1,297 and combines live coaching sessions and video lessons, teaches people how to avoid it.

Despite the widespread use of dating apps, experts like Ms. Hoffman, Ms. Wonderlin, and Ms. Anderson believe that our society as a whole still significantly lacks digital communication skills. The reason, according to Ms. Wonderlin, is that there isn’t one place where people can go to learn how to start and maintain a healthy relationship. Instead, many are forced to figure things out on their own.

After all, texting is still a relatively new communication medium. “Our brains aren’t wired to think in” 100-plus character messages, Ms. Anderson said. While texting is convenient, it lacks the texture and depth of in-person conversations. “Distilling our complex and nuanced feelings into crisp S.M.S. messages is hard, which makes it easy to inadvertently say the wrong thing.”