Best Texting Advice for Mature Daters

Learn the best texting advice for singles who are re-entering the dating world at 50, 60, and beyond. Discover when to text, what to text, and more.

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Peggy and Richard Wolman are matchmakers and dating coaches for mature daters. I interviewed them on Last First Date Radio, where they shared their best texting advice for women and men re-entering the dating scene later in life. Texting is a whole new world of communication, and many mature daters have no idea how to navigate this confusing aspect of the dating scene. When to text? What to text? When NOT to text? I will share highlights of our show in a moment, but first, a little more about my guests. 

Richard is an experienced clinician, author, researcher, teacher and faculty member of Harvard Medical School. He has helped countless individuals navigate their relationships through troubled waters. He recently joined Peggy to coach men and women in their search for love as an organic extension of his career. “Many of our clients have endured extraordinarily difficult life experiences. Hope survives and can generate new, loving connections.”

Peggy is a nationally recognized matchmaker, dating and relationship, workshop leader and speaker, with a Masters in Social Work, Peggy’s professional background is rooted in helping people find their own voices. She knows how to motivate and inspire confidence to help single men and women find love. Match.com and YourTango.com regard Peggy as one of the country’s leading relationship experts. Appearances with her husband, Dr. Richard Wolman, include the The New York Times, The Boston Globe, CBS, This Morning and CBS.com. Most recently, Peggy and Dr. John Gray, (Men Are From Mars, Women Are From Venus) shared a podcast about older adults looking for love. 

How does texting impact mature daters who don’t have the experience or confidence about how to write or interpret texts?

Peggy: Older adults who are re-entering the dating world may have the advantage. For younger daters, texting is their world. They have developed their texting skills. But for older adults, the advantage is that you have to discuss how you view texting and what you use it for. On the date, you can say, “One of the features of re-entering the dating world is texting”. Then, see how your date feels about texting. It’s important to bring up the topic of texting, because you’ll learn about communication styles early on. 

Richard: For older adults, texting is an acquired taste. They have to learn about texting. If they have children, they’ve texted with their kids, and it’s been useful and convenient as a way to communicate. In dating, you don’t text in the same way you’d text your kids. There are different rules and expectations. 

With your kids, you have an intimate relationship. But you don’t have that same relationship with someone you just met. Texting can give the impression of intimacy that’s not yet earned. So you can’t use the same quality of texting with your dates. 

What kind of texts work and don’t work?

Peggy: Texts work for logistics. For example, ‘The train is running late’ or  ‘I couldn’t find the restaurant, and I’m down the street.’ Logistic texting is thoughtful. Also, after a date, if you haven’t talked about it on the date and you want to communicate that you had a lovely evening, try to do it over the phone or email, but you can also text. If he writes to you first, respond in kind. If he writes one sentence, you write one sentence. 

What about emojis? Yay or nay?

Peggy: Women tend to use them more than men. My inclination is that if you’re so inclined, use one, not many. 

Richard: Emojis can also bring emotional context to a text. [You need to bring your emotional self to dating.] The goal of dating is reciprocity. You give to someone, they give to you in a mutual growth-inducting format. 

Peggy: With texting, it has so many variations and the style with which you text becomes your language. If you don’t speak the same texting language, one of you will probably get upset. There’s so much misinterpretation. Don’t take his texting as a sign of who he is and a reason not to see him again. Meet face to face, and get to know him. 

What final words do you have for our audience about texting?

Richard: Texting can be fun and it can be dangerous. Be careful and learn how to use it in an effective way.

Peggy: Even though it may feel awkward, try to find a way to have a conversation about texting. It will likely grow your relationship.