20 Rules For Dating After Divorce: But Really…There Are No Rules

When do you think is the appropriate time to start dating after divorce? I don’t have anyone in mind, just a general question. 13 months into the divorce process. I haven’t moved out yet due to financial reasons. Very ready to try dating.

This email got me thinking about the many many questions men and women have when dating after divorce. So, I decided to come up with my “rules,” but realized that there really are no rules, just opinion.


Here are 20 rules for dating after divorce, but you don’t really have to live by them, listen to them or even like them. They are just MY rules and my humble opinion.


  1. The appropriate time for dating after divorce is when you decide the time is right. That could be one day after you get separated, 5 year after your divorce is final or anything in between. It’s your choice and no one should judge.
  2. Think of dating as meeting interesting, fun, likeable people, not a hunt for your next wife/husband. In other words, take the pressure off yourself.
  3. Ask people to set you up on blind dates. No one is going to think of it themselves, so put the idea into their heads.
  4. Be open minded and not critical. It might not be love at first sight, but it could develop into a genuine friendship and/or a fun friend.
  5. Be a gentlemen. Make specific plans and set a time at least a few days in advance.
  6. Be a gentleman. Pay for a first date always.
  7. Be a gentleman. Always send a text or call to tell your date you had a nice time.
  8. Don’t complain or talk negatively about your ex, your divorce or the fact that you are struggling financially.
  9. Make your date laugh. Keep it light and funny. Smile!
  10. Always walk behind your dates, never in front of her.
  11. Be yourself. Don’t try to be what you think the girl/guy wants.
  12. If struggling for conversation, just ask her/him some questions about themselves. Trust me, the awkward silence will be gone in a second.
  13. Don’t play games. If you like her, don’t wait to call her. We’re not 25 anymore.
  14. A first date must: kiss her good night and stop there!
  15. Remember that women have insecurities and baggage just like you. Be kind and understanding.
  16. Remember that women love older men because they are experienced and they’ve lived.
  17. If you rush into something, so what? Sometimes that happens.
  18. Always practice safe sex.
  19. Be mindful that your dates have jobs, kids and other life obligations, much more so than when you were dating in your twenties.
  20. Just enjoy yourself. You’ve been through a lot. Dating shouldn’t be a chore and there should be no negatives associated with it. Dating should be fun and light and enjoyable! You deserve to be happy in that regard!




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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.

3 Responses to “20 Rules For Dating After Divorce: But Really…There Are No Rules”

  1. Jeff

    Adding to #10…just walk next to her, but take the side closest to the street. Just a nice gesture in a protective kind of way. It may not even be noticed. If it’s crowded, it may actually be a good idea to walk in front a little. Essentially, you’re lead blocking so she doesn’t have to.

  2. Jason M

    Jackie, no offense, but as a man, I can’t take dating advice from a woman. The reason is that most women aren’t honest with themselves about what turns them on, especially not the alpha/beta mating strategy. The courtly-gentleman checkpoints your forebrain came up with above are often in direct conflict with the sexytime cues that your primitive hindbrain actually looks for.

    For example, #6 is terrible advice. Paying for the first date puts a man into “provider” framework in the woman’s mind, the same provider framework that a divorced man has just escaped from, or maybe is struggling within. It doesn’t make him look like a sexy guy.

    So is #12. Lots of women don’t like direct question-and-answer stuff. Better to talk about stuff going on the environment around you. It’s called “grandparent patter” and is a timeworn technique to build comfort.

    #10: Walk in front, behind, alongside her. Vary your steps. An unpredictable man gives a woman happy tingles.

    #15: Be kind? Nope. Women don’t respond well to nice guys, at least not sexually. On a kindness scale of 1 to 10, it’s good to be a 3 or 4. This causes the most cognitive dissonance in women, because it’s hard to admit to yourselves.

    All this is basic evolutionary psychology. I like what you’re trying to do on this blog but it’s not helping men to understand true female behavior. For better advice, I would point men instead towards any manosphere site, such as stuff by Roosh.


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