Dating After Divorce: Top Ten Tips!

Dating after divorce
Neil’s book, “Dating Success After 40”

Ten Tips on Dating After Divorce by Neil B. Wood


Getting through my divorce was emotionally brutal but I knew it was time for a new chapter and positive changes in my life. But going back to dating after being with only one woman for the last 25 years was quite a shock. I had ZERO interest in picking women up in bars. Never have and never will. I did want companionship, fun, and hoped to experience love again and all the wonderful treats that come with it.

I tried online dating with several sites and within days, I was meeting some of the most beautiful, sexy, fun and interesting women I had ever met. The next three years were filled with dates, lessons, and adventures and of course, a few mistakes. I want you to learn from my successes and mistakes, so here I present the Top Ten Tips.


  1. Know exactly what type of person you want to meet THIS time and know your deal-breakers. At our age, we know what we like and what we don’t. I made a list of the ten things I wanted in a woman and found an ideal match after 2 ½ years and 40 dates. Try the online dating sites. Custom-build your profile and create searches to attract your identical match, in the comfort of your own home. Within a twenty-mile range, I found 824 women that met my preferences. You won’t find that in a bar, bowling alley or supermarket!
  2. Trust your instincts during the first date. If the chemistry isn’t there, thank them kindly and wish them the best. Pay the tab (guys) and move on!
  3. If you meet someone online, ALWAYS have a phone call or Skype before you decide to meet in person. ALWAYS! Before you meet for a date, Google their name. There are scammers, former inmates, and other undesirables out there and it’s your responsibility to protect yourself. NEVER loan money to someone that only emails you and is never available for a phone call or skype or date.
  4. Sex: if you really like each other after a few dates and decide to take it to the next step, talk openly about what WOWS each other in bed. Some people are clueless about sex and how to please their partner, and many just left a “sexless” marriage. Read She Comes First by Dr. Ian Kerner and you’ll send me a thank you note. Yes, it’s THAT good and she will love you for being so thoughtful!
  5. First dates should be something inexpensive and brief such as a coffee or lunch. If the chemistry isn’t there, you haven’t spent much and can walk away after an hour.
  6. Online daters: beware of old photos. Your photos should be less than two years old. Ask them if theirs are. People DO lie about their looks, height and income.
  7. Understand what didn’t work in your last long-term relationship. Don’t make the same mistake this time.
  8. Enjoy the moment. Let the past go and begin again. Dating is fun in this new chapter of life. I felt like I was 28 again, but much wiser.
  9. Be a gentleman ~ always! Women are very special and like to be treated that way. Open the doors and pay for the first date at least.
  10. Ask questions about your date’s interests and be a good listener. You’ll be among the top 10% of all guys!


Ok, I can’t resist adding the woman’s perspective to this piece, what I liked and what I disagree with. #1 is my favorite, but I think Neil is focusing too much on online dating. That being said, dating sites are the number one way people meet their spouses. But, I still believe looking for your soulmate is kind of like looking for that perfect job. And what that means is, it will benefit you to network. The best way to get a job (and to meet someone) in my opinion is through your friends and their friends. So, when I say network, I mean, don’t be afraid to ask people through business and your friends and their wives if they know anyone they think might want to be set up. People don’t think of these things on their own. They need YOU to spell it out for them. And, when you do, you will find they are delighted to keep an eye out for potential people for you. Plus, you have the benefit of already knowing someone who knows them! 

I totally disagree with #2, the first date instincts and it infuriates me when men show up, not like the way you look and are out of there in two minutes. Where the hell are you running? Is your time too valuable to make a good friend just because you have no desire to rip off her clothes right then and there? Everyone deserves your time. Everyone. Especially someone who gave up HER time to meet you there. Give her a chance!! She may end up offering you something valuable, like good business advice or she might make you smile or laugh. Maybe you could set each other up with other people. I once cringed when a blind date came to pick me up, because I thought he was short and ugly. A half hour into dinner, I was gaga. Great personality made him so attractive! We dated for 4 months. He broke my heart.

The rest is so so great! I love the one about sex, and I love #’s 7 and 8.

Thanks for a great post, Neil!

Neil Wood immersed himself into the “dating world” four years ago after his 25 year marriage dissolved. He found it difficult to meet single women his age, so he spread the word among his friends and became a member of several online dating sites. As a sales and marketing expert, he quickly realized that to find a match online, you’ve got to know what you are looking for, market yourself with a well scripted profile and share your best photos. He met his ideal match two years ago and co-authored Dating Success After 40 to help others thrive in the dating world. learn more and buy the book:


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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 After Divorce: Top Ten Tips!”

  1. Neil Wood

    Jackie, I like your feedback and want to explain the “chemistry” comment. I’ve had several dates with very nice woman who politely told me at the end of the date, “Neil you are a nice guy but I don’t see us as a match.” I understood and appreciated it. You know how chemistry is. Sometimes our heart practically leaps out of our chest or the conversation flows so well that it’s as if you’ve known each other for years. But sometimes, it’s just not there. We don’t get along with everyone we meet. That’s how I meant the advice on #2. : )
    Thank you for the post and I’m enjoying your site!


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