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Dating Coach Women After 40 | Courtship and Relationship Advice

3 Smooth, Suave, and Sophisticated Dating Tips for Younger Men Wanting to Date Older Cougar Women

Dating Advice:  3 Smooth, Suave, and Sophisticated Dating Tips for Younger Men Wanting to Date Older Cougar Women

Used to be 20 years ago that for a young man to be interested in an older woman, people thought he must be “hard up.”  Nowadays, there is still some residual judgement and bias where people think and whisper to each other, “Well, you know, he must be after only one thing.

But the truth is one of the hottest current trends in dating is Cougar Dating wherein younger men are pursuing older women.

If you’re a younger man and you are attracted to the confidence, maturity, and fun of an older woman, here are 3 smooth, suave, and sophisticated dating tips for you to attract, pursue, and date older women.

Tip #1.  Do Be Smooth:  Go Where The Fish Are

Where do older women congregate?  Are older women really at the same singles bars as the 20 something girls?  In some cases, yes, they are.  In Silicon Valley, Los Angeles, and Manhattan, you will find the sexy successful business executive women rubbing elbows while downing the Chardonnay, Mojitos, Cosmos, or Margaritas together with the 20 somethings just out of college.  And while singles bars are fun, they really can be a mad house.

Where else could you try?  When you want to stand out and not be one of many other single men in the crowd, go to the gym or YMCA classes that women love and attend en masse.  There are always more women in the group classes at the gym because studies demonstrate that women are very tribal and socializers.  Take a yoga class.

Tip #2.   Do Be Suave:  Do Move In When You First Meet and Be Low Key

Now the thing is, while it is a hot new dating trend for younger men to date older women, frankly, not every 40+ year old is thinking that way.  You might need to woo her a little bit about the idea.  Be a man and do approach her.  She will respect your masculinity for this.  However, be a bit more covert.  Be low key in your exchange, and her defenses will go down.

At the end of the class just warmly strike up conversations with the other women.  Be smooth and suave here.  Just strike up a conversation.  Don’t immediately push to get her phone number.  Just say at the end, “I’ve really enjoyed talking with you.  I hope to see you next week.  I’ll definitely be back again.”

Tip #3.  Do Be Sophisticated:  Invite Her Out with You at Your Second Meeting

At your second conversation, she will be more comfortable with you.  That’s when you could suggest, “Hey, I haven’t had my coffee yet, and gotta get some java.  Would you like to join me for a cup of coffee around the corner before you head out?”

You show your confident sophistication knowing that she is busy.  It’s also a compliment.  “You’re beautiful.  You’re successful.  You must be busy.”

By doing that, subtly and smoothly you just let her know it would be brief.  No pressure for too much of anything right away.  You’re just looking to get to know her a bit better in a romantic way.  She will feel more comfortable with you this way which increases your chances of romantic pursuit success your with dating older women.

Happy Dating and Relationships,

April Braswell

Las Vegas Baby Boomer Dating Expert

relationship coach, dating coach, online dating coach, sexual romantic relationships, dating articles, internet dating sites reviews,

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44 comments… add one

  • Hi Marty. Thank you so much for your consideration and thoughtfulness in the heads up. My spam filter already caught it and I deleted it. Thank you for stopping by! – April

  • Rob

    This is not a trend I really understand unless the woman has a lot of money, but I hear about it in the media so I guess it is happening.

    Tell the guys…don’t forget to wear Ashton! cologne when you go out to hunt cougars.
    Seize the Day,Rob N

  • Martin Wright

    If only I was young, free and single…
    Great practical advice, which even includes what to say – good for us shy Brits!

  • Keri Eagan

    Really great tips April.

    Those cougars are lucky women. Smooth is the way to go! I can see this working with a number of women I know.

    Keri Eagan

  • Ok I guess I’m old enought o be a cougar but I don’t have the single status.
    However I think we could teach those younger men a thing or two! :-)

    Good one April


    The Harwood Center – Tinnitus, Chronic Illness, Fears, and Anxiety

  • Nice advice, April. You are an excellent resource for the singles out there.

    Health, Fitness for Working People — Darryl Pace

  • Robert Martin

    I can guarantee you this. If I ever got a divorce (never, but if) I am coming to you for guidance.

    Robert Martin

  • lol! think VEAL in your case! lol

    thank you for stopping by. It was great talking and meeting you (finally!) after all these months via phone. I think our work totally dove tails for people’s benefit and heart healing.


  • Hi Robert,

    thank you for stopping by. You totally crack me up, you are a RIOT. (Does your DW know you have this drole Steve Martin side?)


  • you’re never too young to start robbing the cradle… ;)

  • Katie

    April, dear, you really must stop telling the young men to woo you . . . they should be wooing me! No fair!

    , Katie

  • April, dear, you really must stop telling the young men to woo you . . . they should be wooing me! No fair!

    Cleanse from the inside out, Katie
    Sorry… forgot to say great post – can’t wait to read your next one!

  • Jose Escalante

    Your always entertaining April. Plus I would like to remind everyone that Yes I’m still happily taken.

    Jose Escalante

  • Martin O'Connor


    These 3 steps make a lot of sense and sound like they can be followed by all guys with any romantic intentions.

    There might even be one before the three above.

    The point to all this: The speaker was fun and entertaining, and she demonstrated for the class of all men how to approach a woman. Her first tactic was to get into the woman’s vision without looking at her and give her a chance to size you up. If you are alert you can maybe pick up a stop or go single right there.


  • Men of all ages, married and single could use that advice (married men – for approaching your wife, please!).

    Good work April.
    Expanding spheres of influence, Kate

  • John Ho

    Smooth talking and strategic positioning goes a long way to get what you want out of life!

    But then if you know numerology, you can get to the core drives pretty quickly.

    John Ho

  • Hi Kate, thanks for stopping by and commenting at my blog. lol! Good thing you added that clarifying caveat for my readers. ;) April

  • Scott Payne

    Every time you say Cougar I want to rent the Graduate… LOL
    Great Stuff

  • Being more conservative, I appreciate your post.

    This would probably work, if you were searching for someone younger?

    James Mason

  • JJ Jalopy

    You’re beautiful. You’re successful. You must be busy.


  • I don’t know if I could actually go after a younger guy. I’d always be worried that when his cougar turned grey, he’d be looking for a kitten.

    Lisa McLellan
    Babysitting Services – Babysitters and Nannies

  • Mister P


    Solid information!

    Have you noticed the correlation between dating and sales?

    Bert (alter ego- Mister P)

  • People still pretty much say, “He must be after one thing.” We just don’t want to believe it.

    Steve Chambers, B2B Sale Trainer

  • I am also love with one old woman and these three tips are really helpful for me when i will go for a dating.

  • lol! the women are now, too! Great to see you here Steve. Thanks for stopping by and commenting at my blog. – April

  • Anthony Lemme

    I am sadly too old to pursue cougars…missed my chance!


  • Just found this post & it’s terrific advice.

    For the record, when I was 21 & going to school near L.A.
    I dated a 38 year old woman & it was the best thing to happen to me
    and I would argue the best thing to happen to everyone I’ve been in relationship with since.

    Definitely learned a different outlook on culture, art, conversation,
    fashion & took on a more worldly view of life than i would’ve had I dated
    another 21 year old that summer.

    Never really liked the term “cougar”.

    Instead I always think “Beauty & Grace”


    The Success Secrets

  • Jikar

    it happened that I dated a 40 years old women when i was 28. It was the most sexiest experience I have ever encountered. I saw my cougar in hanging out in the a public garden,but I did not approach her untill she was aware that I am interested. She was a bit older but I could feel a call for love and sexiness not only in her dressing style but in her body langgauge as well. Her calling eyes confirmed her sex appeal. I was very excited to date. She was very mature and confident. I relocate and met a new young date but I can never forget her.

  • Michael D Walker, I found very unique your dating story, however, your views are really appreciative!

    Anyway, if a man wants to date a woman then there are some things that should always be there like honesty, care and a good personality.

    Overall, I enjoyed the stuff greatly, keep it up please!


  • Cathy

    roar. I think younger men are very attractive sexy men.

  • Warren Abbett

    Excellent post for reminding singles to make the effort April. Thanks.

  • David

    Is there a particular place you’d suggest I hang out to meet hot older women? Or is the internet the best place?

  • Daryl

    I like cougar dating. I always wanted to be Benjamin because I thought Mrs. Robinson was hot. Anne Bancroft looked great in that movie. I like that different age dating is more acceptable these days.

  • Aaron

    Women who are a few years older than me are the most attractive. They know what they want and like in men. Less flakey.

  • Cassie

    I think younger men are great. They’re still eager to date and behave like gentlemen.

  • Jacqueline

    This is a great post full of dating tips. Thanks so much for sharing, like always April.

  • Cheryl

    I like the idea of dating younger hot men just they seem so immature. What do you suggest?

  • Randy Feldman

    Once we re all over 40 years old, the age differences don’t make much difference. I think it’s great that women date younger guys.

  • mattam

    i think older women are more confident sexy and know what they want then young women do

  • Maggy

    Hi April. I agree. It’s kewl for older women to date younger men. As a feminist if men can then women should too. What do you think are the best places to meet younger hot guys?

  • Rob Miller

    I feel ok about a dating a woman a few years older than me but not a lot older. That still just feels weird.

  • Chris Petrello

    Lovely just what I was searching for to do better with older woman. Thanks April.

  • Sylvia

    I ACTUALLY don’t agree with you totally April. I think it sounds good on paper younger men with older women. But I just don’t think it works outside of Hollywood. Just look at Susan Sarandon and Tim Robbins. They didn’t make it work.

  • Kurt

    One of my friends has a thing for women 20+ years older. When he was in he early 20s I witnessed him hitting on a just such a cougar who was in her late 40s and he went down in flames! He learned that when approaching an older woman he shouldn’t refer to her as “Madam” as in “Excuse me, madam…”

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