Navigating The Wild World Of Online Dating

There are unclear rules and expectations.

Pixelated red heart on a teal background
Pixelated red heart on a teal background
Dan Saelinger/Trunk Archive

“Good-looking guys come a dime a dozen / Try to find you one who’s gonna give you true lovin’ / Before you take a man and say I do, now / Make sure he’s in love with you, now / My mama told me / You better shop around / You better shop around …”

– From “Shop Around” version recorded by Captain & Tennille

Lisa was excited to meet a new man. They had talked on the phone and had a good conversation. When they met he was kind and interesting. She checked in with her feelings, and found herself to be comfortable and attracted. But when two days went by with no word from him, Lisa sank into despair. She didn’t know what to make of his behavior. She sent me this note:

Dear Joan,

I met Karl last Friday. It was a lovely dinner, I felt very comfortable with him. Sunday in the morning I sent a link about a movie we had been talking about. He answered me late at night,“I really liked your company, but I felt that you had no interest in me.

His message surprised me a lot, I answered that I enjoyed his company, too, and if he could explain what I did to make him think that I had not liked him. He wrote to me early this morning that he was sleepy, and later he wrote telling me that today he has a long day traveling.

These messages created a lot of anxiety in me. I am working to recognize my feelings and my thoughts and to calm myself down. Thanks for helping me to move forward wisely.

I responded:

Lisa, this is the uncertainty of online dating. By its nature, dating can lead to disappointment and anxiety, because you don’t know this person and you don’t know how they are going to respond. I remember the first online date I went on. He was a very nice man, and I was very surprised when he didn’t follow up. So, I sent him a message. He was honest, and replied that he was not that interested in me. It was a shock to me as we had had a nice conversation. What I have learned since then is that some men are attracted to you and others aren’t. There is no way to know why a man is “into you” or not. Remember this to maintain your sanity while you meet many new men on the path to finding the one who will be crazy about you!

Welcome to the brave new world of online dating: a world with unclear rules and expectations. A world you will have to learn to navigate. But no matter how daunting this world may seem to you, odds are that this is where your soul mate is.

How can the generation that came late to the technology and social media party keep up with the mores and practices of this new world? You will need to learn to face the many challenges of online dating, including: How do you create a profile that represents you well? What to do if you don’t get responses? How do you sustain yourself in the face of rejections?

And how do you get confidence presenting yourself when you don’t look like you did in your younger days? What do you do about these extra lines on your face, or extra pounds on your hips? You may be plagued with questions including: Will a man ever want me? Don’t men only want younger women? Don’t men only want sex?

You would love to have the companionship of a compatible man, but do you have to meet so many losers or be rejected by so many potential partners to find him? If you are not sure if you can do this, you are not alone. Women who are dating online are finding that they need a lot of help and support to get through this maze.

And help is available. There is an entire industry built around providing advice for online dating. There are sites, coaches and newsletters. Start doing your research. If you needed to find a job, you would learn how to navigate the world of online job searching. And you would be persistent in the face of failure or rejection. You need to apply the same kind of commitment to your love life. It is just as important.

Another woman, Sue, shared with me what it was like to be divorced at age 60 after a 38-year marriage to someone she had met in high school. She told me, “I didn’t know how to date!” Through activities like singles groups, she met a few people. And she went online for a year, but it was hard: People she liked didn’t respond to her. People who responded to her weren’t great matches. One guy who she went out with for a few dates wrote her to say they weren’t compatible. She said, “That hurt!”

But she was determined, saying, “I really did want someone in my life to grow old with.” With coaching, she learned how to set up a good profile and how to reach out to men online. She learned that for every five people she wrote to, maybe one would respond. She learned: It doesn’t mean anything if a man doesn’t respond. Don’t take every rejection personally. Meet many new people and stay open-minded.

She went on coffee dates to meet a variety of new men, and met almost 30 people over a two-year period. It wasn’t easy, she says: “I wanted to quit at certain moments.”

The coaching encouraged her to keep going. Her coach told her, “You’re doing well, you’ve caught a few (that you tossed back). Keep fishing!”

Shortly afterward Sue met someone who shares not only her values, but also a common set of friends from their youth. They are now into their fifth year of happily loving each other. You have a lot of love and energy you want to give someone. If you want a partner to share this precious time of life, “Don’t give up! Keep fishing!”

Joan Bragar is a certified Calling in “The One” coach and the author of Never Too Late for Love: The Successful Woman’s Guide to Online Dating in the Second Half of Life. She holds a doctorate from Harvard University. And she happily remarried a man she met on Match.com when she was 62.