How to Get Prepared and Stop Flailing Away at Dating


How to Get Prepared and Stop Flailing Away at Dating

I think looking for a good man is a lot like looking for a good job. You have to:

* know what you want,
* know what you have to offer,
* always keep your eye out for opportunities,
* be prepared, and
* become an expert in your craft.


Read it again. It’s true, right? Or do you question my last couple points? Maybe you think that you just need to be yourself, and when you meet the right man it will simply click.

As they say: how’s that working for you so far?

It’s true that a huge part of attracting a man is to just be yourself. When a man sees you as being authentic he translates that to confidence. And you know confidence is a man magnet.

But what about all the “stuff” that comes up in the course of getting to know someone? How do you show your best side? How do you start a conversation or save one that’s turning into a mess? How do you show a man you’re interested without looking like a desperate floozy? How do you respond to questions you’d rather not answer just yet? How do you share about your horrid divorce, your weight-loss surgery or your long term celibacy?

There are ways to do this that render the best results. You learn how to communicate effectively with your boss, your clients and your Mother. Why wouldn’t you learn how to communicate effectively with men you want to date and with whom you want to develop relationships?

One of my private coaching clients, Janet, had this challenge recently. She went out with a man for a second date. The man had been single for 16 years and she wanted to ask him why. What had he been doing for all those years?

I have very personal experience with this since I was single until I was 47. When I was dating I got the “why haven’t you married yet” question a lot. It never came off as sounding like a nice or reasonable question. Every time it was asked I assumed that it carried judgment. And although I was (at that time) a horrible dater, even I knew that talking about past relationships on first dates was an absolute no-no.

So Janet and I worked on how to ask her date the question without a) offending him, and b) devolving the conversation into a long talk about past relationships.

She also had the flip-side of the problem: she wanted to know how to address the question of her divorce. This always comes up, doesn’t it? Most people dating over 40 are divorced. I think most ask this just to start conversation on a common topic…but it shouldn’t be discussed until later in a relationship. You don’t want to bond on the bad stuff.

Janet’s divorce was messy and painful. She knew she had to give some answer when asked about it, but she didn’t want to discuss any details until she knew a man pretty well.

So Janet and I got to work, and I guided her through creating her two “Prepared Statements.”

Asking the difficult questions, avoiding over-sharing, showing interest or rejecting someone; these all are things you should think about. You don’t want to just jump in and say whatever comes to mind in the moment.

This isn’t about making things up or being someone you’re not. And it’s not about trying to anticipate everything that may come up during a date. (Geez, we over think enough as it is!) This is about thinking of the few delicate things that may arise, and then considering how to ask or respond.

It really is like looking for a job: you try to anticipate the hard questions and prepare yourself with a positive, yet honest response.

Article contributed by
Advanced Member

Bobbi Palmer

Dating Coach

The Dating and Relationship Coach for Women over 40 and founder of Date LIke a Grownup.
Register for Bobbi's free monthly webcasts Grownup Girls' Night Out: Let's Talk About Men! where she gives you tips and tools about dating, sex, relationships and more!


Location: Long Beach, CA
Credentials: Other
Specialties: Communication Problems, Dating/Being Single Support, Empowering Women, Wellness
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