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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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{ 46 comments… add one }
  • April Braswell September 22, 2009, 3:01 PM

    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 September 22, 2009, 4:55 PM

    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 September 22, 2009, 5:23 PM

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

  • Keri Eagan September 22, 2009, 5:42 PM

    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

  • Jennifer Battaglino September 22, 2009, 7:03 PM

    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

  • Darryl Pace September 22, 2009, 7:17 PM

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

    Health, Fitness for Working People — Darryl Pace

  • Robert Martin September 22, 2009, 6:19 PM

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

    Robert Martin

  • April Braswell September 22, 2009, 8:27 PM

    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.


  • April Braswell September 22, 2009, 8:27 PM

    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?)


  • April Braswell September 22, 2009, 8:28 PM

    you’re never too young to start robbing the cradle… 😉

  • Katie September 22, 2009, 9:34 PM

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

    , Katie

  • Katie September 23, 2009, 1:19 AM

    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 September 23, 2009, 1:19 AM

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

    Jose Escalante

  • Martin O'Connor September 23, 2009, 4:22 AM


    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.


  • Kate McKeon September 23, 2009, 6:50 AM

    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 September 23, 2009, 6:58 AM

    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

  • April Braswell September 23, 2009, 8:46 AM

    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 September 23, 2009, 10:15 AM

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

  • James Mason September 23, 2009, 4:11 PM

    Being more conservative, I appreciate your post.

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

    James Mason

  • JJ Jalopy September 23, 2009, 3:23 PM

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


  • Lisa McLellan September 23, 2009, 7:27 PM

    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 September 23, 2009, 8:02 PM


    Solid information!

    Have you noticed the correlation between dating and sales?

    Bert (alter ego- Mister P)

  • Steve Chambers September 23, 2009, 9:44 PM

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

    Steve Chambers, B2B Sale Trainer

  • cable September 23, 2009, 10:07 PM

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

  • April Braswell September 23, 2009, 10:25 PM

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

  • Anthony Lemme October 1, 2009, 7:32 AM

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


  • Michael D Walker April 11, 2010, 4:42 AM

    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 August 22, 2010, 1:26 PM

    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.

  • Alex Pablate September 9, 2010, 1:36 AM

    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 December 16, 2010, 10:40 PM

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

  • Warren Abbett December 20, 2010, 5:31 AM

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

  • David December 25, 2010, 7:20 AM

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

  • Daryl December 27, 2010, 7:57 PM

    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 December 28, 2010, 7:38 PM

    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 December 28, 2010, 9:58 PM

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

  • Jacqueline December 28, 2010, 11:59 PM

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

  • Cheryl December 29, 2010, 8:51 AM

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

  • Randy Feldman January 1, 2011, 8:06 PM

    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 January 10, 2011, 5:06 AM

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

  • Maggy February 27, 2011, 6:14 AM

    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 March 10, 2011, 12:42 AM

    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 March 19, 2011, 3:59 PM

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

  • Sylvia March 23, 2011, 9:52 PM

    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 May 1, 2012, 3:06 AM

    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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