0037 – Six Critical Rules for Dating Someone Older

“In this episode…”

…We’re discussing the art of dating someone much older than you.


Teaser Bullets

by the end of this episode you’ll learn:

  • Why people ‘Date Up
  • What is the etiquette when you’re ‘dating up’
  • Talk about how to integrate with an older crowd

Describe the problem

…Because our listeners are awesome, they send us cool show ideas. This show was requested by Hokie Fan, and the request went like this:


Until last year, I was with my wife for 15 years and when it ended, I seriously lacked the confidence and dating skills necessary to get back out there.  So naturally, I gobble up all of the advice I can find, and podcasts are a great vehicle for receiving this wisdom!


The young woman (she’s 25, I’m 38) I’m dating now and I are getting more serious, and there’s a dynamic to our relationship that I haven’t heard discussed in any books or podcasts that I’ve encountered so far: spending time with each other’s existing friend (and family) base and merging them together.  Particularly when my group of friends (and family) are quite different from her group of friends (and family).


I would love to hear what insight the two of you have into this aspect of dating in a future podcast!

Segment #1

  • Why people ‘Date Up
    • UNBLUSH |
      • Top 3 Reasons to Date Older Men
        • Older and Wiser – Due to sheer time, older men usually have more experience in the dating and relationship area, meaning they have already experienced the highs and lows of relationships. Hopefully they have learned from their mistakes and won’t repeat them with you. It also means they have more to offer you in regards to life decisions such as finance, career, and of course, making relationships work.
        • Romance – Put simply he’s not into playing games, recognizes a good woman, and treats her as such. He may not have always been a gentleman so he may take on the attitude, “been there done that.” Being a player probably faded with the 90′s or early 2000′s, so he calls it like he sees it, meaning he is ready to treat you not as number one but his only one.
    • Men’s Fitness |
      • 7 Reasons Why You Should Want to Date an Older Woman
        • She can make you a better man – A friend of mine dated a 40-year-old woman when he was 22 and new to New York. “She picked the restaurants, paid for things, took me places. She had access to a world I didn’t, and she had done all the things I hadn’t done yet,” he said. Now he’s in his mid 40s, and married with a kid, and remembers that relationship as critical to making him the man he is now. “As a dude, I’m told that I’m supposed to date girls my own age and take care of them, pay for dinner, and so on. But for that period of time, the roles were reversed. She had the power. And it felt great—who doesn’t want to be taken care of?
        • She knows what she wants, and doesnt – And at this point, she’s not afraid to say it. In the bedroom? Go ahead and try to shock her. Bondage? Bisexual encounters? Threeways? Role play? If she hasn’t tried it herself, she’s likely considered it. Plus, I’m talking about outside of the bedroom as well… Since she’s got a little life on her (and maybe even a marriage in her past), she may not have the rigid checklist that a younger girl has. Most of the single women I know over 35 just want a good man, period.
  • User Stories
    • Facebook User
      • My story: went to Jamaica with this older gentleman NEEDLESS TO SAY…he couldn’t get enough stamina to breathe on it!!! Partied with the islanders and told him to lose my number when we got back!!!!
      • No, I hadn’t never slept with him but hell it was a FREE trip and I wasn’t saying NO!
  • Reasons for dating up:
    • Shanna – I didn’t date younger because men/boys were not mature enough nor had drive
    • Akara – I dated two guys 10 years younger than me …but we didn’t relate on the generational things like music and shows etc. and [they didn’t know] how to treat and keep me. I dated a guy 2 years older and he end up losing his job, moving in …but we related on generational stuff and he cooked and made sure we sat at the table together for dinners……Age is truly just a number cause the older guy was less stable and no more ready to settle than the younger guys.
    • Bo – …it’s funny bc all my life I have dated upward. As of lately I would be open to dating a few years younger. But is she can’t cook, it’s not going to happen.lol
    • Valerie – …probably the way that they carried themselves (swagger), wiser, and also seemed like they could offer more in EVERY aspect. Men (younger than me) didn’t seem to have that or I felt like they could not offer the same. I guess I correlated age with the ability to provide – emotionally, physically and all.

Call or text 508 444 2003 to tell us your interracial dating and relationship stories.

Segment #2

  • What is the etiquette when you’re ‘dating up’
      • Just a Little Bit of Everything |
        • 7 Tips For Dating An Older Man
          • DO NOT CONSTANTLY REMIND HIM OF YOUR AGE GAP – If you both have agreed to begin dating, you have moved past whatever age gap you may have. It can come across as insecure *and insensitive) if you constantly remind your man that you weren’t born when his favorite song was released or that you were only in elementary school when he was trying out for the high school football team. you also run the risk of making your man feel like an old man, which could be awkward for the both of you. Play it cool and keep the age jokes to a minimum.
          • Not to say that a woman NEEDS to know how to cook and clean in order to entice any man, but it’s certainly an attractive trait when men are looking for the woman they want to marry and raise their future families. So, show off your skills in the kitchen! Your older man is sure to appreciate it.
          • Many young women are attracted to older me because of their great conversation. This is your chance to talk about all the nerdy things your friends your age rather not talk about. Because let’s face it: most 20 year olds are not interested in talking about buying their first home, retirement plans or even traveling around the world. This is the stuff your older man would LOVE to talk about. So, here’s your chance! Let your inner nerd/responsible adult loose!
      • About Human Pheromones |
        • Tips For Dating An Older Woman
          • Know what you want in life. An older woman is probably aware of what she wants in her life and she will be turned off with a guy who does not know what he wants in life. It is important that you have figured out your goals for your future and you have focus. Older women do not like uncertainty and this applies to men that have many issues in their lives.
      • You Young Now.com |
        • 5 Tips For Younger Guys When Dating Older Women
          • Don’t break promises – Even if it’s in the beginning of your relationship, you always want to keep your promises. Never make promises that you can’t keep as this is a sure way to annoy an older woman and show her how immature you are. So if you say you are going to call at a certain time, give her a call at that exact time. Never make a promise that you can’t keep. If you can’t do something – then simply let her know.
          • Be funny – Humor goes a long way when dating older women, so you should learn how to be funny. Sometimes you can mix humor with sarcasm and this will really show her how intelligent you are. Remember, women just want to have fun. So make her laugh on a daily basis if you can.


    • How do you interact with your partners friends when they are out of your age group


We want to hear from you! Call or text 508 444 2003 to tell us about your older/younger dating stories.



…if you want more GOOD advice like this for free, keep listening to this podcast and also visit to grab “How to Get the Guy” or “How to Get the Girl.” It’s a five day course, packed full of great stuff for you to improve your dating life.

In Closing

In closing, on behalf of myself, Elijah R. Young, and everyone involved in bringing this show to your ears, we hope we’ve made your relationship better today than it was yesterday. Now go forth and relate to one another…we’ll talk soon.

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