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43 Big Mistakes Made in Older Women Younger Men Relationships

Younger men dating older women make these mistakes

If you've ever been in an older woman and younger man relationship you've had your hands full. If you only have experience dating women your own age or younger there are some big mistakes that you need to avoid. Fortunately for you, we have asked 43 dating experts to share the biggest mistakes that younger men are making. Make sure you don't become another guy who can't handle an older woman.

Top Mistakes in Older Woman Younger Man Relationships

Avoid these mistakes and maximize your chances:

1. Trying to "copy and paste" what an older guy would do

Kezia Noble ProfileKezia Noble - Kezia-Noble.com


A younger guy will often try to ‘copy and paste’ or even out match an older guy. This is a pointless strategy because they both offer something totally different.

Older women don’t go for younger men because of their stability, their life experience or their achievements. They go for them because of their ‘happy go lucky’ attitude and their self-belief. Younger guys need to work out what the older guy is lacking rather than what attributes he has. - Kezia

2. Acting more like a friend than a potential lover or boyfriend with older women as a younger guy

Dan Bacon profileDan Bacon - TheModernMan.com


For most people, sex drive does decrease with age. However, that doesn't mean that a woman wants to be with a man who she feels no spark with.

If a guy wants to be successful at dating and getting into a relationship with an attractive older woman, he needs to ensure that he actively creates a spark of sexual and romantic attraction, rather than only being nice and friendly. - Dan

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3. Younger men in relationships with older women fall into a "junior" role

Scot Mckay profileScot McKay - DeserveWhatYouWant.com


Sometimes younger men may be in awe of the older woman's experience a bit.  Remember, having a plan and leading accordingly turn any woman on, regardless of age.  Yet, some guys let themselves fall into a "junior" role with an older woman, which soon leads to loss of attraction. - Scot

4. Handling her the same way you would a younger woman

Cheyenne Bostock profileCheyenne Bostock - AskCheyb.com

One of the most common mistakes I see men make when dating an older woman is handling her the same way they would a younger woman. Older women tend to be more mature, which may appear to make some of the things a younger man might do seem out of character, which ultimately makes the older woman feel uncomfortable.

The solution is to be conscious of the age difference, and to cater some of the activities throughout the relationship to also suit her needs. - Cheyenne

5. Using text as your main form of communication

Lucia profileLucia - HowToCatchACougar.net

The biggest mistake younger men are making with older women is treating them as if they're the same age or younger. Older women are generally not interested in constantly texting or being asked out via text.

Also, they will not respond to men on dating sites or social media if the message is something like, "Hi" or "Hello". There are many more men interested in relationships with older women than there are women available, so younger men need to bring their "A" game. - Lucia

For guys who are pretty good at text communication already, or want more practice, there are some really high-quality cougar dating sites out there that we recommend. Try them out and see the results we saw.

6. Not speaking up

Susan Winter profileSusan Winter - SusanWinter.net

Remember that your opinions count. Just because she's older (and presumably wiser) doesn't mean that she gets to call all the shots. There are two people in this relationship. You'll need to get comfortable exchanging roles as to who leads. It's an equal partnership.

This attitudinal choice works to your benefit. You're establishing that you're the man. Yes, you work with your mate. And yes, you listen to her wants and needs. But you have your own ideas and approach. In order to keep the passion and desire alive, she needs to see and feel your strength. It's an animal thing. Women need to know they have a real man by their side; capable, decisive and confident. - Susan

7. Trying to act older and like someone else

Marni profileMarni Kinrys - WingGirlMethod.com

To be honest, this mistake is something that happens for everyone but more so for men who are dating older or younger. They forget to own who they are and respect the fact that they are younger/older.

The biggest error a man can make is trying to be someone else other than himself. What guys can do is really get clear on who they are as a man. If they like video games. Own it and talk about it with passion. If they like politics…. same thing.

Don’t give up on what you are because you think someone else of a different age is going to want something else. Owning yourself as a man is the sexiest thing a man can do! - Marni

8. Not figuring out what your needs are and communicating them

Radio Wright profileRadio Wright - eDatingDoc.com


If you are going to date an older women you can use the opportunity to learn and grow. An older women will definitely appreciate honesty.

Really try to figure out what your needs are and communicate those needs honestly. Don't be scared to let her know who you really are. - Radio

  9. Younger men in relationships with older women get too attached

Girls chaseChase Amante - GirlsChase.com


Younger men frequently get too attached to older women. Remember, she's been around the block a bunch more times than you have, and this is less of a big deal to her than it likely is to you. So try not to get too melodramatic. She might think it's cute, but if she usually dates older men she's used to guys who are a little more grizzled with her.[/su_quote]

So try not to get too melodramatic. She might think it's cute, but if she usually dates older men she's used to guys who are a little more grizzled with her. - Chase

10. Younger men around older women try to show off and impress

James Preece profileJames Preece - JamesPreece.com


Many men make the huge mistake of trying to show off and impress older women. You don't need to try too hard and overdo things. It's the small gestures such as remembering things that are special to her or cooking a nice meal that are much more important. - James

11. Letting insecurity ruin a good thing

Claudia Cox profileClaudia Cox - TextWeapon.com


If you are constantly asking yourself (and her) ‘why does she want to be with me?’, then you’ll find that she won’t want to be with you for long!

Even though she is older, she still wants you to be the protector, to make her feel safe. She also wants you to take the lead and have a plan – for example, a date idea or a weekend away. - Claudia

12. Thinking that the only thing that older women want is sex

Robert Manni profileRobert Manni - RobertManni.com


Younger guys who date older women almost always fall into the trap of thinking that the only thing that older women want is sex. That may be true in some cases, but for the most part, one of the reasons so many desirable older women are in the market for a partner is that the older men they've dated did not share emotional intimacy, a heartfelt romantic connection, or make them feel respected as a person.

Never take an older woman for granted. She will notice everything and she'll break if off if she thinks you only want her for sex. - Robert

13. Forgetting older women can be very playful, fun and enjoy doing things that bring out their sexy side

Carmelia RayCarmelia Ray - CarmeliaRay.com


Statistics have shown older women to be significantly more sexual than younger women and I've found men to be very lazy in their courting process. If that's not reason enough to date an older woman, I don't know what is!

Although older women have strong sexual urges and sometimes a lot more (sexual) experience, men do not take the time to properly court an older woman to have her interested in him and find him sexually appealing. Sorry guys, older women (cougars) are simply not just DTF whenever you call. - Carmelia

14. Letting yourself be controlled or pushed around

Kari profileKari - AttractGetWomen.com


A woman is a woman - old or young, and they are, for the most part, drawn to a man who can take charge, make decisions, and stand his ground. This doesn't mean that they want a jerk, that's not what I mean at all. They want a man who will stick up for himself and be supportive and protective, even if they can support and protect themselves. - Kari

15. Younger men put older women on a pedestal in relationships

Justin Stenstrom profileJustin Stenstrom - EliteManMagazine.com


The biggest mistake I see men make is putting older women on a pedestal. They think because the women are older, the rules of dating and attraction don't apply to them like they apply to the younger women. But they couldn't be more wrong in this assertion!

All women respond to the same attraction triggers. And no single woman is off-limits. If an older woman is out and about looking to meet men, have the utmost confidence in yourself that that man could be you. And use what you know about dating and attraction to give yourself the best chance at dating her. - Justin

16. Bringing up sex too early

Sandy Weiner profileSandy Weiner - LastFirstDate.com


The biggest mistake men make when starting a relationship with an older woman is to bring sex up too early in the relationship---like on the first phone call or first date. Many men want a guarantee that they will have good sex. So they want the goods up front.

The problem with this is that older women feel like these men objectify them. They want good sex, too---all in due time. So, get to know these amazing women first. Sex will come, and when it does, it will blow their socks off! - Sandy

17. Dirty Dog Syndrome

Dennis Work profileDennis Work - Guyvorce.com


It’s what I call “Dirty Dog Syndrome.” Guys think they are God’s gift to the world and that all those much younger women will just flock to you. So when you’re dating an older woman, your Dirty Dog comes out of its cage, and you get a serious case of roaming eye.

You’re not paying attention to your date or caring about her as a person; you’re fantasizing that you’re Hugh Hefner. And you don’t have to say a word, because she can tell. Which means you will end up: Alone. - Dennis

18. Not asking enough questions

Jill Crosby profileJill Crosby - GreenSingles.com


If you share (or dump) how your day was right off the bat and then don’t ask about her day, it appears that you are not very interested her life and therefore her. It’s not necessarily that you are not interested; it’s just that you don’t always think to ask. So, if you are dating an older woman, make sure to ask her about her day, her feelings and her dreams. Ask her what she wants for her birthday if you know it means a lot to her.

Be a good support to her, as she most likely is to you. Make sure to LISTEN when she talks and don’t cut her off. Let her talk it out. Sometimes women need to talk to figure things out. We don’t always want solutions, sometimes we just need to talk and bounce ideas off of you (or vent).

If you have a good solution, ask if she would like to hear it rather than assume she would. Be patient, we don’t always get to the point right away, and sometimes there is no point. Bottom line, listen more, talk less. - Jill

19. Trying too hard to impress her

Scott Valdez profileScott Valdez - VirtualDatingAssistants.com


A guy in his 20s who is dating a woman in her 40s shouldn’t try to act more mature than he really is, or pretend to be wealthier than he really is. Researchers have confirmed that most women who use online dating sites have serious concerns over the authenticity of the guys they are messaging. Breaching her trust early on can stop a budding relationship in its tracks. - Scott

20. Putting aside your vision of the future and not being honest about what you really want

Damona Hoffman profileDamona Hoffman - DamonaHoffman.com


If you want to have kids but your lady is at a time in her life where she doesn't or can't have children, be realistic about the fact that this can't be your forever woman. Likewise, if she has kids and you don't see a future with them in your life. Too many times I see couples postpone or abandon their dreams because they fall in love - or in lust - and think that problem will just work itself out.

Usually you can coast through the relationship for a few years but if you have a major difference in how you see your future, eventually your relationship will crumble. - Damona

21. Falling in love right away

Chris Manak profileChris Manak - ManicWorkshops.com


Again, older women have life experience. They have been through the dating process to a much greater depth than younger women (for the most part) so they know that immediate love is fleeting love. They differentiate between lust and love. They do not want to deal with a needy boy smitten after one date, they want a man on their level. - Chris

22. Younger men act immature

Lucy Clarke profileLucy Clarke - WeLoveDates.com


Cheeky jokes might work with an older women in moderation, but immature jokes won’t. When you're in an older woman younger man relationship she may like younger men, but more often than not, to keep her interested, you’ll have to have a mature mind. - Lucy

23. Pretending to be someone you're not

Karen Poter profileKarenLee Poter - KarenLeePoter.com


Dating an older woman is challenging if you aren’t feeling good about yourself. Women want to be with a self-assured man who’s got his ducks in order. Because older women have dated quite a bit, they don’t have time for nonsense and game playing.

Older women can see through the bullshit quickly, so be honest. When taking her out on dates, pick something affordable. She realizes you’re younger and aren’t the CEO of a Fortune 500 company. If she wanted that, she wouldn’t be interested in you. She wants companionship and fun so be yourself and continually try to do some self-improvement.

It’s a turn-on for me as a self-proclaimed “Cougar” to see a guy who takes the lead, listens to the woman he’s trying to woo, and has a positive confident attitude. - KarenLee

24. Playing into her insecurity

Rachel Russo profileRachel Russo - RachelRusso.com


We live in a society in which women are already insecure about aging and having relationships with younger men. The worst thing a man can do is play into that insecurity. For the most part, large age differences between partners is more socially accepted when the man is the one who is older.

When women are older, the stereotype is that their boyfriends or husbands will cheat and/or trade them in for a younger model. Men need to be aware of and sensitive to this. They should not draw attention to the age gap with their comments or behaviors.

Too many younger men give women reasons to be insecure. They are interacting with younger women on social media--liking one too many pics! They are being secretive about who they are texting--having their phones on the table, facing down. Really?! This is just a recipe for making an older woman even more insecure! - Rachel

25. Not listening

Rachel Moheban-Wachtel profileRachel Moheban-Wachtel - RelationshipSuite.com


The biggest mistake I see men make when dating an older women is not listening and talking too much about themselves. - Rachel

26. Tell me a secret about you no one else knows

Jessie Kay imageJessie Kay - TheRealMatchmaker.com


As older woman we are highly unlikely to share any kind of scintillating fact we have with someone else... after all we just met you!

You're putting us on the spot forcing us to recall something unusual, intimate and ‘crazy’. As a mature woman we just find this childish and dirty-birdie. No good can come from this. - Jessie

27. Trying to impress them

Dan Munro profileDan Munro - TheInspirationalLifestyle.com


Trying to impress them, which is actually the biggest mistake I see men making in all forms of dating. But this is particularly relevant to older women, because they've seen it all before and they know you're full of shit.

They have become worn out with the falseness of the modern man, so when they meet a guy who doesn't give a damn but is still genuinely interested in them, it's like a massive breath of fresh air. Let them see what mood you're in, tell them stories that are actually true, have a laugh and let go of trying to think of something good to say.

Act like you're hanging out with your best mate and have nothing to prove (with the exception of also expressing sexual attraction when it occurs). - Dan

28. Don't tell her she reminds you of your mother

Lisa Shield profileLisa Shield - LisaShield.com


Never tell an older woman you’re dating that she reminds you of your mother or any other “older" woman. Also, don’t mention that she is the oldest woman you’ve ever dated. And don’t tell her that you love older women.

If you really want to flatter her, tell her she reminds you of someone younger and even more beautiful than her. - Lisa

29. Texting!

Denise Levy profileDenise Levy - MissMatchMakerLive.com


TEXTING! Keep in mind that texting is one of the easiest ways to be misunderstood and leaves too much room for interpretation. Older women like to know where they stand.

Picking up the phone and actually calling her shows her you are mature, have good communication skills and that you value her. She will feel appreciated much more with a phone call instead of a brief text. - Denise

30. Younger men often make some bad assumptions

Shimrit profileShimrit Elisar - OnlineDatingBook.co.uk


The biggest mistake I'd say is making assumptions. Just because a woman is older doesn't mean she's going to look or act in a certain way or want a particular thing out of a relationship.

Regardless of her age, a woman is still an individual and needs to be treated as such. I think some men forget that and are surprised when the woman they're dating doesn't fit the bill. - Shimrit

31. Men rush

Doc Love profileDoc Love - DocLove.com


Women fall in love slower than men. Do not talk about the future or make a date on a date. No Texting and wait a week to call after each date. We want her to contact you for a date. Let her touch you, but do not touch her back. We are creating a Challenge for her. - doc Love

32. Younger guys dating older girls fetishize the process

Joshua Pompey headshotJoshua Pompey - NEMVIP.com


Don't treat your date or partner as if she is someone that you are knocking off your bucket list or fulfilling a cougar fantasy with. Women don't want that. At least most don't.

If you are dating an older woman, treat her with the same respect that you would treat any other woman. They are people with feelings, not items to knock off your sexual bucket list. - Joshua

 33. Getting into a relationship when they're not ready

Melissa Josue profileMelissa Josue - HappyHealthyRelationship.com


Being ready for a relationship includes knowing what you want, but it also includes resolving any issues that might undermine the success of a relationship--like having a lot of unresolved emotional or legal baggage from a previous relationship or not having effective dating and relationship skills. - Melissa

 34. Making fun of her age

Damien Diecke profileDamien Diecke - SchoolOfAttraction.com.au


Making jests about the age difference are big mistakes, even if she laughs along with you. It should be obvious advice, but women can be self-conscious of their age, and that come out the most when she's dating a younger man. - Damien

35. Prejudging a woman

Shanny profileShannon Tebb - ShannyInTheCity.com


I would say the biggest mistake that men make when in a mature woman younger guy relationship is that prejudgement. They look at an older women and think she wants marriage and babies tomorrow. This isn't always the case.

They may just want to find a great partner to have a relationship with. Or they critique why they are still single. Another mistake, is not to feel threatened by them. Show them support and be interested in their life and passions. Try not to be too submissive.

At the end of the day, an older woman wants to be taken and not always be the one to make the decisions. Be a man with a plan and stick to it! If you need to cancel a date, don't just batman. Explain yourself and rebook. - Shannon

36. Trying too hard to play it cool

Sarah Ryan profileSarah Ryan - SarahLouiseRyan.com


Mistakes in dating are across the board but those looking for love a little later in life know what they want, they have more often than not had a long term relationship, if not a significant other resulting in marriage, and so more importantly; they know what they don't want.

I think playing it cool and waiting a certain amount of time before contacting, arranging for a second date or even picking up the phone for a telephone call won't really wash. It would bode well to be direct, forthright and using honesty in feelings as the best policy for finding love with someone who is just that little bit older. - Sarah

37. Letting her become the boss, or sort of like a mother

Eddy Baller profileEddy Baller - UltimateManBuilder.com


The biggest mistake I see guys make is letting her become the boss, or sort of like a mother. It's easy to let this happen because older women have more experience and will often be more assertive than younger women. Many of them are mothers too and will see you, the younger man, as someone who needs babying (if you allow it).

If you just sit back and not take on the role as the man then she will. In the end it will be a turn off for her and bad for your Independence and confidence. I made this mistake when I had less experience. - Eddy

38. Not being upfront with how you feel

Her Smile ProfileCosmo Currey - HerSmile.com


My answer is not tied specifically to older women but to relationships and dating in general. The biggest mistake people make is not telling their partner exactly what they feel. Often the fear of retribution outweighs the human necessity to express their desire.

To create a relationship with someone older, younger, same sex, different sex we have to be unequivocally clear as to how we feel and what we want. Be it sexually, emotionally and mentally needs have to be aired. Without that you core communication goes out the window and you’re left with a façade of repressed emotions. - Cosmo

39. They want energy to match their own

Patrick King profilePatrick King - PatrickKingConsulting.com


Making and acting on assumptions. A younger man might have a host of assumptions about an older women who is seeking a younger man, but I guarantee that 99% of them are false or incorrect. The 1% that is always true is simply that they find younger men attractive and fun to be around.

Don't assume you know what they want, or that they are a "cougar," or that they are just looking for a fling. To people who are frequenting this site, the phrase "age is just a number" is common. Keep that in mind and approach them with an open mind. - Patrick

40. The biggest mistake with older women and younger men comes at the beginning

Dave Perrotta profileDave Perrotta - PostgradCasanova.com


The biggest mistake comes in the beginning phase, when young guys are meeting and trying to attract older women.

The older women gives the younger guy an age objection, and he doesn't know how to respond.

Basically, she says something like, “You’re fun, but I think I’m too old for you. You should hang out with cool and attractive women who are your age.”

So, how should you respond?

What NOT to do: Argue that you're old enough for her or why age doesn't matter. This is a logical argument and will ruin the attraction and connection.

What you should do instead: Agree and exaggerate. Use the age difference to create a fun and flirty conversation.

For example:

Her: "How old are you?"
You: "25."
Her: “What?! 25? I’m 31!”
You: “31? Wow, you’re way too old for me. This would never work. You’re just going to try to take advantage of me and all my innocence.”

By agreeing and exaggerating, you make light of the situation and it doesn't seem like a big deal anymore. In doing so, you beat her age objection and continue the interaction with her smoothly. - Dave

41. Making a big deal of the age gap

Sebastian Harris profileSebastian Harris - GlobalSeducer.com


The biggest mistake that younger men tend to make with older women is that they make a big deal out of the age gap. If you approach an older woman with "I know that i am a bit too young for you, but you look really beautiful", you convince her subconscious mind that you are in fact too young for her.

Congratulations, she won't give you her number and she definitely won't go out with you. What to do instead? Don't even mention your age. Act as if approaching her would be the most normal thing in the world. - Sebastian

42. Going on the defensive from the start

Matthew Valentines profileMatthew Valentines - PersonalDatingAssistants.com


The biggest mistake guys make is going on the defensive from the very start. "I know I'm younger, but..." Don't do this. Instead, approach from a place of supreme confidence. Tell her that dress looks incredibly sexy and sophisticated on her.

Sincere compliments actually WIN points with older women. We never do this with younger women, because they hear it all the time. Older women appreciate it more, and are less likely to take your interest for granted. - Matthew

43. Don't focus on your differences

Julie Ferman profileJulie Ferman - JulieFerman.com


Don't mention it. Don't focus on it. What's the big deal? Men have been "dating younger" for ages, and unless the age difference is extreme (more than 7 or 10 years) it's rarely an issue, unless he or she makes it an issue.

Our youth-obsessed culture will naturally cause a wee bit of insecurity for a woman who's dating a younger man. The most attractive, alluring quality that men seek in women is confidence.

Help her build and maintain her confidence by treating her as a person, not a number. Chances are... she's gonna outlive you anyway, as women live an average of 5 years longer then men do, so stay together for love and because the relationship works well for both of you, and let go of your attachment to what a modern-day love is "supposed" to look like. - Julie


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