7 Clever Dating Tips I Learned From 30 Years Of Playing The Field

Stop wondering why he didn't call and whether he likes your body.

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I dated for three decades. Yes, that’s 30 years of dating before I met and married my wonderful, hot, loving husband at the age of 47. So, when it comes to dating advice, I know what I speak. If there was a mistake, I made it, probably more than once.

Now I’m a 50-something, happily married, dating and relationship coach specializing in helping women over 40 find forever love. I clearly see the dating mistakes I and many women make over and over again. In hindsight, I can see the things I did and didn’t do that clearly led to unnecessary angst, loneliness, and frustration.


For the past 10 years, I’ve helped countless women avoid the traps that kept me stuck and frustrated. Here are 7 dating tips for women I wish I’d known 30 years ago.

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Here are 7 clever dating tips I learned from 30 years of playing the field: 

1. Stop ruminating on why he didn't call.

Countless hours of mental energy, conversations with girlfriends, glasses of Chardonnay, and buckets of popcorn are spent and consumed trying to unravel this age-old mystery. Well, I finally have the answer to “Why didn’t he call?”


Here it is: I don’t know. Neither do you, and there's a good chance you will never know.

Men understand (better than women sometimes) that dating means meeting a bunch of people until the special one comes along. The bottom line is he didn’t call you back because he knows something you don’t know yet: He’s not right for you. You are not his soulmate, for whatever reason.

He’s not calling you for the same reason you chose not to continue dating other guys. You don’t want to because it’s not right. Lots of reasons. Doesn’t matter. So, the most important dating tip for women ever: Move on quickly.

2. Don't mistake a good date for a good mate.

Do you know when you meet a man who has The Thing? The Thing that makes you feel giddy and a little breathless? It’s called “chemistry” and we tend to take it very seriously. So seriously that it often trumps all other data.


It’s like once you decide he’s hot and possibly "The One," all contrary evidence is invisible or seems irrelevant. Out the window, it goes. You’ve seen your girlfriends go all ga-ga over some hot guy when it’s obvious to everyone else that he’s a bad match. That is what chemistry does to us.

If you want to just sleep together, go for the hot men. But if you want to be adored, challenged, trusted, loved, and humored, learn how to think past that superficiality to find the real good guys.

Sure, you want to be attracted to him. But to make the good choices you have to find out what’s underneath the looks and charm and get past the idea that you have to feel all giddy when you meet him.

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3. If you can’t talk about it, don’t do it.

I’m not talking dirty flirty “you’re so hot” talk. That’s easy. I’m talking about Talk, with a capital T. If you’ve got love on your mind, wait until you can talk with him about your expectations, what having sex means to you, your worries and hopes.

Most importantly, if you can’t sit down with him and have an adult conversation about safe sex and about your relationship, do not sleep with him. I’m all for having fun and enjoying some amazing intimacy, but it will be so much better once you’ve opened up communication with him on a deeper level. This will limit your disappointment and help you find the happiness you deserve.

4. Don't expect men to act like women.

They're different. Do you know why we are so often disappointed by men? Because we expect them to behave based on how women would act. It’s all we know.

We don’t leave room for men to be men. We consider how they think and feel, but it’s generally not based on any real knowledge; it’s based on how we would think and feel.


One of the keys to finding a fabulous man to share your life with is to commit to learning about men. When you do, you will find that men are not wrong — they are just different. Men are so different from us, and once you “get them,” you’ll see their magnificence and absolutely love them like I and so many women I work with do.

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5. Stop "Premature Baggage Bonding."

PBB is when a first or second date shifts into a “deep” conversation after you discover some baggage you have in common. It starts off innocently with a question like, “So what happened with your marriage?” And off you go! The talk begins about your horrific ex-spouses. How they were alcoholics or cheated or were bad with money.

Maybe PBB begins when you proudly share your sobriety and start sharing your history of addiction. Or one of you talks about a health issue, and before you know it you’re comparing the scars of your knee-replacement surgeries or trying to one-up each other about your horrible hospital experience.


None of this is sexy. None of this is attractive. None of it creates a positive start to a good relationship.

In the beginning, stay in positive territory. When things start to shift in the conversation, it’s up to you to say, “Wow, I had a similar experience. Maybe once we get to know each other better we can share more.” Then change the subject.

6. Embrace your body just the way it is.

We women are much more hung up on our bodies than men are. If a man is out on a date with you, that means he likes your body. If he’s a grown-up, he knows you have given birth. He doesn’t care! Or, if you have surgery scars or a few extra pounds, again, he doesn’t care.

There is a distinction between a body "falling apart" and simply changing. Just because your body looks different than it did 20 years ago doesn’t mean he doesn’t think it’s beautiful. After all, he’s now got a paunch or much less hair than he once had.


When you get into bed with a man for the first (or hundredth) time, he’s not thinking about your cellulite. He’s thinking that he’s getting into bed with a sexy woman and how much he’s going to enjoy your body.

Be open to the fact that what the media portray as attractive doesn’t match with what real-world men believe. Be open to the fact that when men compliment you they sincerely mean it and accept it graciously.

Self-criticism and putdowns of your looks are so much more of a turn-off to him than your wrinkles or sags. The factors that make the largest impact with respect to your attractiveness are within your control: they are your warmth, femininity, and confidence.

7. Bring your warmth and your feelings to your dates, not your resume.

If you don’t dig your femininity and your softer side, he won’t. Guys get plenty of intellectual stimulation and left-brain conversation from work and with their golf buddies. Yes, he wants a smart woman, but he already knows you're smart. He is looking for an emotional connection with you. If he doesn’t feel one he will move on.


I have a technique you can use to help you confidently express the deeper, softer you and draw in the right man in a big way. At the same time, it helps you get to know and love yourself. It’s a bit of a trick. I call it “Getting to the Because.” Because statements look like this:

  • “I’m a hairdresser and I love it because I get to be my own boss and be creative. I love helping people feel and look beautiful, and many of my customers end up being my lifelong friends.”
  • “I became a dentist because that’s what my parents wanted me to do. I’m good at it and I like it, but these days I focus more on what I want, which is to learn all I can about sailing so I can sail around the world someday.”

You can get to his “because” too by asking, “Why?” When he is telling you about his work, his kids, and his hobbies, you can ask, “Why?” Why does he run marathons? Why did he choose his profession?

Do you see how using “because” and “why” makes it completely different than just spewing out your job title and your accomplishments? I’m a hairdresser. I’m a dentist. I run marathons. Snooze.

Using these two words helps you share some really juicy stuff about your character, personality, values, and dreams. And all in a sentence or two.


Being in your feminine means being more open with your feelings and expressions, and with that comes some vulnerability. But know that this is your strength. Not just because it attracts the right men, but because it’s fun. It’s the only way you will get to experience the real man-to-woman relationship that you want and deserve.

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Bobbi Palmer, founder of Date Like A Grownup, is an internationally recognized expert helping women over 40 find grownup, lasting, passionate love with the right man.