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Dating Tips for Mature Women: 7 Signs He’s Bad for You (and 7 He’s Got it Bad for You!)

By Shirley Goldberg March 09, 2022 Dating

If a guy really likes you, he wants to be with you. Common sense. But what about in the beginning, before it’s a relationship. How do you know a man is interested then?

At our age, it’s not like you’ll see him in fourth period English, and you’re not thrown together on the dance committee after school. Interaction is more random.

Plus, nowadays, we’re hyper-aware everyone’s busy with work, projects, and grandchildren, so we text rather than phone. And with the pandemic, things got even worse.

We’re particularly reluctant to bother someone we don’t know well, for fear of overstepping boundaries before a relationship gets going.

When it Comes to Mature Dating, Beginnings Aren’t Easy

When it comes to dating, there are certain signs that show a man’s interested. Even if he calls only once a week to ask you out, if he keeps in contact, it’s a sign of interest.

If a man asks questions designed to get to know you better, that’s a start. If he asks follow-up questions to something you told him a few weeks earlier, that’s even better.

My friend Diane says she knew Bob really liked her when he took her to the symphony. “When we’d been dating a bit longer, he told me he hated the symphony. That’s when I knew he liked me.”

Forget the words, go by the actions. Another friend swears by what she calls the “little niceties,” meaning, opening the car door, taking her out for a bite when she’s had a difficult day at work, or taking her grocery shopping.

“On our third date, he brought me home and walked me to the door. I sort of groaned that I’d forgotten to drag the trash can to the curb. ‘Open the garage door and I’ll do it,’ he said. He endeared himself to me with that small, thoughtful gesture. And he hasn’t stopped doing little things to make my life easier.”

The Beginning of a Relationship Is an Important Marker

People don’t change. A man will show you from the first who he is. Based on whether you have an easy or a difficult start, it’s for you to decide if you want to get to know him better.

“I went out with Doug once and had a great time,” says a close friend who’s a teacher. “But when he called for a second date, I had already made plans. ‘I can’t cancel on Peter,’ I’d told Doug. ‘He’s my friend and it’s his birthday.’”

“‘You’re taking him out for dinner when I’m asking you out?’ Doug said, his tone so demanding I almost hung up on him.”

Should You See Him Again?

My friend continued going out with Doug for several months. “Now that I look back on our time together,” she says, “I knew who he was from the beginning. I ignored my gut feeling partly because he made me laugh and he was a great dancer. But he had moods and demands, and in the end, he was bad for me. I broke up with him.”

Time will tell. Sometimes, a short time will tell you what you need to know, and that will save you the anguish of a nasty breakup down the road.

Should you see this guy again? We’re older and we know more. “Listen to your own smarts,” I tell my friends when they ask for advice.

Listen to your gut, too, and use your experience in dealing with people to avoid making mistakes that cost you time lost with a toxic man.

Here’s how to tell if you’re special in his life. (Although I’ll bet you already know.)

7 Signs He’s Got it Bad for You

  • He calls you. If he can’t, there’s an email or text message because he’s thinking of you and likes to keep in touch. He’s not constantly on his device when you are together.
  • He wants to see you two or three times a week. More if he can. It doesn’t have to be a big production every time you get together. He enjoys picking you up and going for a simple after dinner walk to the park, for example.
  • He talks real purty and his actions match his poetry. He is affectionate and likes to be close to you.
  • He doesn’t promise anything without following through.
  • He talks about stuff you’ll do in the future – wine tasting, hanging that gigantic painting you’ve had propped in your living room for five months – and you actually do it. Together.
  • He likes planning the next get-together early in the week, even before he’s left on a Sunday evening.
  • He’ll root for the Yankees with your 93-year-old mom, and he hasn’t told her he’s a Red Sox man.

7 Signs He’s BAD for You

  • You’re down to getting together once every other week. Or less.
  • He texts. Sometimes. The phone calls, though, are all business plans for the one-night coupling.
  • The pretty talk occurs either before or during sex. He doesn’t show affection or touching outside of sex.
  • Chew and Screw takes on an all-too-literal meaning since there’s not much in the way of activity other than sex.
  • He talks about stuff you’ll do in the future. The future becomes the past.
  • He doesn’t make plans ahead of time. He likes to be spontaneous. He’s also spontaneous about cancelling.
  • Your mom? He isn’t aware she’s alive and well and loves baseball.

If you have to ask yourself whether he likes you and is interested in being in your life, he probably isn’t. A man who truly likes you will show you that he cares and will not leave you confused and wondering.

Beginnings aren’t easy. Neither are endings, and unhappy endings are the worst. If you’re looking back at several past relationships as a waste of your time, consider going more slowly in future ones.

Better not to go exclusive with one man too soon. Take your time getting to know him in different circumstances. Meet his friends. Let him meet yours. Hold off on the intimacy.

Reread the seven warning signs above. Have you been in any of these situations? What did you do about it? How did you know he was interested? Did he say or do something that clinched it for you? What senior dating tips would you like to offer? Please share your experiences, the good, the bad, and the ugly!

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The Author

Shirley Goldberg is the author of Middle Ageish and Eat Your Heart Out, both romantic women’s fiction with seasoned characters. Her website,, offers a humorous look at living single and dating in mid life. Shirley’s friends nag her to tell them which stories are true in her novels.

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