Dating After Divorce: How to Play the Game with a New Man

Dating Game Kim, a divorced woman of 51, is one of my over 40    dating coaching clients who complained to me this am in her session about a new guy she just met. Kim has a lengthy list of criteria about the men she will date. Still she manages to meet several men every week without fail. Men seem to be every where she goes – no shortage for Kim. Unfortunately, 99.9% don’t measure up.

Red Flag #1 – He’s Not Divorced
Sunday night, Kim met Phil at a local restaurant/bar that she frequents. It’s an upscale place that attracts a solid over 40 crowd. She met Phil who is a good looking guy of 48 who is not quite finished with his divorce.  (Hope you are reading this and thinking – Red flag)

They had a great time at the bar. Fabulous banter ensued. He’s got a great sense of humor, is very intelligent and up on what’s going on with the world, engaging, and the right chemistry. Kissing in the parking lot followed the evening of fun.

Phil got Kim’s number, said he’d like to take her kayaking under the full moon and out for drinks next Friday night. Told her he’d call to shore up the details.

Kim’s First Mistake – Prompting
Tuesday, Kim sent him a text – just something light and funny to “prompt” him. Kim wanted to reinforce her interest. (Oh no Kim, not “prompting”) him. If you’ve read my stuff or heard me speak you know I consider this the error zone. He already asked her out and she said yes. How much more interested does she need to be?

Kim feared that Phil might not follow through – that’s the real motive behind her actions. And so, in the hopes of ensuring her date for Friday night, she sent him a harmless text.

Do Nothing
Is this a big deal? Well it’s not the end of the world. One little light-hearted text isn’t a lot of chasing. But I do believe the best course of action when a man asks you out is to say yes, and then do NOTHING. Let him call you, follow up, set up the date. You just show up, enjoy yourself, be appreciative and make him feel good if you like him. Nothing more is required.

Kim’s Second Mistake – Trying to Close the Deal
Well, Phil did call her by the magic Wednesday deadline, but at 10pm. Kim didn’t want to call back that late and couldn’t pick up the phone when it rang. She did call back the next day, leaving a message. But not the best feminine energy message. She explained how she didn’t want to call too late the night before (that’s fine). Then she went on to ask him to leave a message about Friday night’s plans. (oh oh, not the best next step)

Phil did respond, but not with any clarity. He texted back – “full moon Friday night?”

You can imagine Kim’s reaction to this dodge.  “What is that? That’s not an answer! What am I supposed to do with that?” After Kim took a deep breath and calmed down, I explained that in fact, that WAS an answer. He was sending her mixed signals and acting non-committal – because that’s who he is right now.

Phil’s Situation
While it’s true that Phil asked her out, if she had left things alone, she probably would have figured out sooner he’d be a “no show.” Prompting a man, and trying to the close the loop on plans can backfire. It can scare a man away, even though it seems like simple etiquette and how you’d proceed in business.

Except this isn’t business.

The Bottom Line on this Scenario is:

1. Phil isn’t a good bet any way because he’s not divorced yet or recovered. Even though everyone recovers  differently, he hasn’t even finished his divorce yet. I advise avoiding these guys. They are usually flaky – just like Phil. He may be a great guy, but he is no where near ready for consistent dating.

2. Texting, calling, emailing – any of these prompts before the first three dates have passed are ill-advised. Resist your urge to purse him, follow up or take charge in any way. You look more interesting when you are aloof, so sit back and entertain yourself in others ways rather than wait for “his call”. Bite you tongue, but don’t initiate communication.

For more details on how to find love and play the dating game to win, get a copy of MANfesting Mr. Right

Photo credit: Lester Public Library

Single for too long, Ronnie wanted to find love. She put her skills from personal development and her spiritual path to work, dating 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to manifesting and midlife dating, she founded It’s Never Too Late to help smart, successful women find love or live an empowered and magical life. Ronnie Ann Ryan, MBA, CCC, is a Certified Coach who has helped 1,000s of midlife women with her Love & Magical Life Coach services. She’s the host of the Breathe Love & Magic podcast and has been featured on NBC, ABC, & Fox News, NPR, BBC, eHarmony,, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

8 thoughts on “Dating After Divorce: How to Play the Game with a New Man”

  1. Great advice Ronnie! I am a guy and I agree, guys who are separated are not a good prospects for serious relationships. I don’t think there is necessarily anything wrong for going out to have a good time nor do I think of that as necessarily a complete waste of time, but for the purposes of finding out whether this guy might be the right one for Kim, I think your advice is right on.

  2. Hey Ronnie,
    Okay maybe i’m slow today but i missed something here: how was he being noncommittal/flaky? Because that Friday wasn’t actually a full moon and who knew when the next full moon would be so it was a non-date to begin with? Or because he didn’t give a time for the date?

    I agree that her texting him wasn’t the best plan and all of that, but i’m confused about how he was flaky. I apologize in advance if the answer is obvious and i just missed it!

    • Hi Jen,
      Sorry for the confusion – he knew the full moon was Friday – that’s why he suggested kayaking under the full moon. The flaky part is that when she asked him directly about plans – he did not answer even though he had asked her out for Friday. Hence, flaky in my book. Hope that clears it up for ya!

  3. Ronnie, great post. I agree entirely about not dating anyone who hasn’t divorced. Still unfinished business in my book. I also believe that time alone is also needed between relationships, to find ones self again and to allow time to leave the “coupledom” dynamic and feel what it is like to be alone and in a happy space, rather than short circuiting this time and filling it straight away with another relationship. What are your thoughts on the guy that has been separated for years, but has never divorced ? I get quite a few men contacting me on a dating site that have been separated for many years without the final paper work. I say no to them too, but I have a female friend who has been separated for 10 years who thinks I am over reacting. What are your thought on this Ronnie?

    • Hi GoGirl – Regarding people who are separated, like Terry said – if he’s not divorced, he’s still married. Separated is not divorced. If you are looking to marry, I advise – don’t go there.

      Many folks separate for financial reasons and don’t plan to marry again, so they don’t need freedom. However – the ex is still in the picture at some level. It wouldn’t be my first pick for a serious relationship – maybe something more casual, but everyone is different.

  4. Great post, Ronnie. I’m with you all the way on this one.

    If he’s not divorced, he’s married. Not a good bet.

    He said he’d call. Give him a chance to prove whether or not his word is any good. Let the guy call you.

    But, back to the fact that he’s not divorced: Why would the woman even waste her time?

    • Thanks Terry for your feedbac. I like the simple way you put it – if he’s not divorced, he’s still married – Excellent point!

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