How to Make Men Better Daters

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Recently I did a radio show about dating advice from my book “Mom…You Just Need to Get Laid: The Adventures of Dating After Divorce”. Besides talking about the funny stories in the book, the male host asked me a provocative question: What are the mistakes men make that cause women not to be attracted to them?

Ah, I thought. Men, just like women, often unwittingly do things that come off wrong. The vast majority are likely unaware of those habits. And yes, I admit, there are a few that know what they are doing and do it anyway.

The audience for the show is millennial men, aged 25-40. The host hoped that I could help them catch bad habits early so they could become better daters. That age group includes both singles and divorced. The advice I offered applies to both.

See what you think about my top four answers!

1) Men are shy about approaching women. Why’s that? Because they haven’t developed the conversational skills that make them feel secure. The reason dating apps are so popular — not only because it’s possible to meet more people quickly — is because you don’t have to actually talk to a potential date…as least not at first. Despite what we think, men (especially shy or introverted ones), don’t always know how to ask a woman out on a date.

IDEA: You ask the man out! I am serious. Perhaps it wasn’t acceptable when we began dating (some!) years ago, but now it’s also practical and appropriate. In my book, I tell the story of Stefan the Scholar, an internationally known speaker, who presented the keynote at a conference I attended. I was so impressed that I worked my way to the head of the crowd of thousands and introduced myself. We went on a date a month later where he confessed he had not dated in 25 years! He didn’t want the obligation that comes with dating. I asked him out on the next date and he said yes. And we had a great time.

2) Men come on too strong. And I don’t mean being physically aggressive. They may have an agenda, everything from finding a girlfriend, to wanting a Friends with Benefits relationship, to looking for a wife. The story of Saul the Sailor in my book is all about a man who vetted me to be his bride (a role I had no intention of playing). He wanted to make sure I could carry the water with his family, friends, and business colleagues. “I can take you anywhere,” he pronounced. It was all about him, all the time.

IDEA: Know where your boundaries are. You know what you are wiling to give on. You decide what’s right for you. It’s not just about the man demanding what he wants. It’s always about our knowing what we want and being clear about it. Trust me, it makes building a healthy relationship easier for both parties. (Spoiler alert: I didn’t marry the guy!)

3) Men don’t know how to go on a great date. I love it when a man has a plan. Call me old fashioned but I want the date to be romantic and fun. It doesn’t have to cost a lot, but it does need to be creative. One of the most inventive dates I went on was with Levi the Lawyer who treated me to a pottery making class for my birthday. I still have the drink coasters I made that night and get compliments on them all the time.

IDEA: Create a list of things you want to do on a date. Don’t be stingy about sharing them. My list includes touring the Empire State Building, a carriage ride in Central Park, a scavenger hunt in the City, a ride on the Ferry, walking the canyons of the Financial District, finding the best New York pizza and more. I’ve done them all with dates and had enormous fun.

4) Men aren’t courteous about checking in. Have you ever been on a fantastic date and then don’t hear from the guy for days? When he finally does get in touch, you are furious (or anxious), and he acts as if there is nothing wrong. I’ve just discovered “The Great Kominsky” on Netflix, a fabulously written and funny show (at least the first two seasons) about two men who are working through the indignities of aging. Alan Arkin and Michael Douglas are the co-stars, and they deliver every line in perfect pitch. In one episode, Michael Douglas’s character Sandy Kominsky has a sleepover with a woman he has been dating for awhile and really likes. Then he doesn’t call her for a week. By the time, he does, she tells him off. He talks her reaction over with Alan Arkin who suggests he has to make HUGE amends for that lapse of judgment. Watch the show! It’s great.

IDEA: If you don’t hear from the man in a couple of days, send him a text. It should be brief and friendly, and it should also include a question he needs to respond to. That question can be casual (like “How’s your dog feeling?” in my Cain the Canine Lover chapter of the book) to more intentional (like “I want to see you again. The next one’s on me. When can we make that happen?)

Next month we will talk about what qualities men most look for in a woman. In the meantime, feel free to send me a note at I always look forward to your questions, comments, and dating stories!








  • Kate Somerset

    Kate Somerset is an author pen name for the book “Mom…You Just Need to Get Laid: The Adventures of Dating After Divorce”. Following a divorce after 24 years of marriage, and thirty years of being deeply rooted in professional and volunteer roles in Texas, Kate took a chance on a new life in New York City. She immediately fell in love with Manhattan and the many opportunities it offers. Kate’s book about 15 true dating experiences in New York City is an honest, humorous, and inspirational look on how to give yourself and romance a second chance. One of the most universal struggles faced by all of us – building effective social connections – is the focus of Kate’s monthly column for The Three Tomatoes. Published by Brooklyn Writer’s Press, the book and Ebook are available on Amazon. An audiobook produced by The Three Tomatoes is on Amazon and Audible. Learn more about Kate at

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