Dating Advice for Men: Baby Steps!

Hey DGS, Have any dating advice for men? I’d like to know how to approach a shy woman who is turned off by a confident, outgoing, slightly aggressive guy such as myself.


OK, here’s the deal—the honest truth. Yesterday, I was at my son’s basketball tournament and brought my computer to try to get some work done in between games.


I read this question and was prepared to give my advice, when it dawned on me that there were two men (dads of other 13 year old basketball players) sitting next to me. So, I read them the question and asked, “Any advice?”


One of the dads responded with what I thought was excellent advice! The first words that came out of his mouth were, “Baby steps.”


He then went on to give this advice:


“All it takes is figuring out what might be important to that woman at that time. Maybe she just bought a new outfit, a new purse. Give her a very nice, quick compliment and be in and out. In other words, don’t give her the time to get flustered or embarrassed or feel the need to respond to it. Give her a “quickie compliment” and then leave.


She will be left there knowing someone feels something nice about her. That’s your in.


Baby steps. Be patient. Now that woman has this nice perception of you. You’re no longer a stranger and you’re not a stalker. The next time you see her, expand on it. Maybe give her another compliment with a question about her day. Then, you’re out again. Same as the first time.


The key is patience.


Any good fisherman knows that if you yank on that line you might tear the hook right out of the fish’s mouth. You will scare the fish and never see it again.


Slowly gently, reel the line in. Next time you see her, ask her a few general questions. Ask about her past. Make her feel at ease, and never make her feel pressure to respond to any of your covert advances.


All that said, let it be known that your feelings are sincere and honest. Don’t lie. Just tell the truth in a complimentary way. It really is a piece of cake.



After a few interactions where she feels no pressure and you are not a stranger, just a nice guy from the neighborhood, approach her for a casual meeting– either coffee or lunch-not dinner. Plan to meet at the place, it’s not a date.


The coffee date will tell you everything you need to know. If the cup of coffee lasts 4 minutes, you know to be on your way. If it’s an hour, then you know you have the green light to ask for a more serious date.


The key to everything is baby steps. Nothing that is ever rushed ends up being a good thing.”


I love this approach! Give it a try and please let us know if it was a success!

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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorced Guy Grinning is a blog for men facing divorce and dating after divorce. It's kind of like hanging out with your platonic female divorced friend and hearing her perspective on your divorce and your love life issues.

One Response to “Dating Advice for Men: Baby Steps!”

  1. Ellen Feldman

    Perfect advice. A divorced woman needs to feel a man is a friend or at least friendly before considering a date. It will take time for her to trust again. Baby steps!


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