Six Problems With Dating Older Men

by Thembi Ford

When it comes to dating, I’m way too open-minded.

Last year, I realized that maybe I should start having stricter standards for who I’ll date. You know, require that a man own a home, have a job, stuff like that. Finding those restrictions a bit picky, a friend and I devised a new strategy: We’d spend 2010 focusing on dating older guys. It made sense: they have good jobs, they’re settled and own homes, and they’ve finally gotten to the point in their lives where they know how to treat a woman. We called it the “Grown Men in 2010” challenge, and endeavored to meet as many men at least ten years older than us, but not old enough to be our fathers, as we could.

After about a year of this nonsense, I learned that dating the grown and sexy is just not for me, for six good reasons:

1. Throwback Vocabulary. I dated Steve, 41, and he was a fun guy, but half of what came out of his mouth seemed like it was from a House Party 2 outtake. He regularly referred to sex as “getting busy,” or “knocking boots,” which is a lot more of a turn-off when such phrases are used on the first date, believe me. The idiosyncrasy that would finally drive me crazy was his habit of shouting “boo-yeah!” whenever he made a particularly funny joke, saw something interesting, or really just anytime he felt like it. Being around him was like reliving all of the most mediocre catch-phrases of 1992.

2. Throwback Fashions. I could not deal with Sam’s wardrobe, and as much as I know all 42-year-old men don’t dress as badly as he did, I’m still sort of traumatized. He probably never dressed well anyway, but he somehow stopped updating his look around the time that ribbed turtlenecks and Rocawear cargo jeans were hot, and he’s not the only man of his age that I’ve seen rocking pants that look inspired by the Michael Jordan Jean Collection. Huge patches, odd-stitching, and random rips in your grown man denim isn’t just unattractive, it’s embarrassing.

3. The Haircut. When I first met Will, 42, he admitted that he needed a haircut, an admission that wasn’t necessary because it was clear that he did. Dude was wolfin’, but I’m opened minded so I took his number and we arranged a date. That night he showed up well-dressed and with a fresh cut alright – a flattop. It wasn’t even a full-on flattop, just short enough on the sides and full enough on top that it was clear he was still aiming for a played out style – the Kwesi Mfume, if you will. Not cool.

4. Medications: I got over myself about Sam’s wardrobe and started seeing him more seriously. One day, I opened up his medicine cabinet (I know, I had no business) and a bottle of Avodart tumbled out. I spent the rest of the evening wondering what exactly the stuff was before finally Googling it – the drug treats prostate enlargement. We’re all human beings in a state of constant decay, yeah I get that and none of us are safe from medical problems. But I’m not ready to think about anybody’s prostate for at least another decade. Let’s grow old together, dude. Don’t beat me to it.

5. Grown Kids. Will had a 21-year-old son who still lived at home and was a real cutie, much more so than his father. I’d be lying if I said I didn’t do the math and realize that although he may not have been old enough to a rent a car and could barely buy alcohol, this kid was closer to my age than his dad was. These “cougar” scenarios appear so often in Lifetime movies and bad erotica that I blame pop culture, not my inappropriateness, for noticing what a fine little tenderoni the young man was…until he started addressing me as “Ma’am,” and then eventually “Miss Thembi,” extinguishing all of my cougar dreams.

6. Immaturity. What, you thought that older men are more mature than young ones? Nope. I mistook Steve’s immaturity for a good-natured and kind of simple personality. He turned out to be the type of guy who mainly cared about drinking and hanging out with his raggedy friends, a group that was thinning by the year as it lost members to wives, careers…you know, actual adulthood. One day Sam invited me to a family barbecue and I found out that his entire family still calls him “Boobie,” and his mother will do an occasional load of laundry for him. Grown men who still go by childhood names? I’ll pass.

Although dating a “grown and sexy” man may seem appealing, I found that it just wasn’t for me. Having to deal with inappropriate wardrobes, brothas who mamas still washed their clothes, and men perpetually stuck in 1992 just wasn’t for me. From now own, I’ll stick to men my own age, thanks.

Have you ever dated an older man? Would you?

  • African Mami

    I believe and adhere to age is nothing BUT a number. It is all about that chemistry and vibe we have with one another, that will make me not run after realizing that he is dealing with an enlarged prostrate…instead I will nurse him, after calling 911 to take him to the nearest hospital for surgery!

  • bluedove

    This was laugh out loud funny! And yes, I have been there. I don’t know if you ever went “there” with one of your older beaus, but you could have added to the list the “inconsistent” er, um…”equipment”, though they tend to be very attentive lovers, and not as much in a rush as their younger counterparts… Great read!

  • Timcampi

    Omigosh stop talking! Ever since I discovered Hugh Jackman (when I was nine) I knew dating older men was for me! Haha. I’ll give you six good and biased reasons.

    1. The older the sometimes wiser/more educated.
    If you’re going out with an older man, chances are he’s “been there” and done all of that. He has more insight and more to offer in the relationship. Granted he might always think you’re wrong and inexperienced, but chances are he’s right. That waffle will give you heartburn when you’re older.

    2. A job.
    I’m assuming if you’re dating well into the AARP league (I’m a seasoned champ myself!) Your boo has got a job. He’s got money, and he’s logged the hours. He’s a no bullsh*tter and a real go-getter. Just give him a dose of aspirin first.

    3. Experience.
    IN BED.

    4. He doesn’t want anymore kids!
    Chances are he’s got one or three of them, and you kind of look like the third one anyway. Oh god there’s no way he’s having a baby with his baby-faced baby! And if you ever feel the urge, you can always breastfeed the 11 year old…

    5. Naps
    During the day! It’s like God just INVENTED 3:45 pm for Tempur Pedic. Amirite? Laaaddddiiieeeeesss~!

    6. He looks like Hugh Jackman.
    Oh wait he doesn’t? Well… why are you doing this then. Ewww he’s oldddd.

    [In all honesty I think older men are awesome. I think younger men are awesome too! But guys my age are bogged down with college and don't want relationships. I like the depth age adds to the relationship. I've become wiser in some ways, and I've learned to cherish small things.]

  • African Mami

    @ Timcampi,

    high five to all that and then some.
    I had to google Hugh Jackman…Dang that brother is fine! But, IDRIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIS takes the cup!

  • Unknown

    That was funny. One thing I have learned is that older does not always mean mature. I like my me older than me, yet closer to my age from 3 to 6 years older than me with a few exceptions (Idris Elba ;-)

  • chanela

    whats the male version of a “cougar” called? oh yeah… a perv. lol why is it bad for men to want 18 and 19 year old women?

    LOL i could totally imagine those ribbed turtle and jean cargo pants from 2002 LMAOOOOOO i was dying! i know old men with them damn patch jeans and shorts/ ahaha i can’t stand when older men try to dress “hip” i swear if i see one more 60 year old man in a tight ass hollister shirt im gonna scream!

  • getmelolly

    Despite the 6 reasons, I still think grown men are the way forward. I can forgive the throwback vocab and wardrobe.

  • CaliDreaming86

    I’ve never dated an older man before, and I don’t ever plan to either.

  • CaliDreaming86

    “whats the male version of a “cougar” called? oh yeah… a perv. lol why is it bad for men to want 18 and 19 year old women?” – SEX.

  • WIF

    I met someone recently who I thought was interesting – smart, funny, good-looking, yet not that secure in his life – no F/T job but ‘working’, no phone – he says it’s because he ‘doesn’t need one,’but I didn’t believe him – and some other issues , but very minor. Found out that he has a girlfriend. I thought that perhaps we could just be friends, because the above made me suspicious, but what bothered me was that his girlfriend is 22 and he is 39. That screamed “control issues” to me, and weirded me out. I’m closer to his age and I guessed that he was interested in me because he wasn’t able to have the discussions that we did with the GF. I joked about his GF’s age and he got really defensive and this was telling: “I’m young and I take care of myself. I didn’t know that there was a appropriate age for relationships.”

    In his case, I surmised that because he was conscious of the fact that he didn’t have the material things that someone his age ‘should’ have, and dating a younger woman ( who is in college) meant that she might not be so quick to judge him as someone my age would. Also, he seems to be one who is not that willing to compromise and perhaps this girl lets him take the reins of the relationship. More pliable, I guess. However, another male friend crudely summed it up as, ‘pu**y must be tight!’ He admitted that it was ‘creepy,’ but on the other hand, if Russell Simmons can date 20+ year-olds and he must be in his fifties, why not?

    I just wonder what these relationships are built on – similar interests, great sex, someone that makes you ‘look’ good in public, or a chance to control someone else? As a single BW in my early 40′s, I wonder if this will be another reason to be passed over, but on the other hand, too many red flags for me!

  • RealityCheck

    If you are a 30 something year old woman maybe you should stop being so picky. Lets face it…Your options have greatly diminished. So instead of bashing men who have far more options than you (even if it’s only because they have a larger dating pool) , maybe you should seek out some humility, and a reality check.

  • char

    I’ve never dated older guys but my boss would date girls my age and he and his friends would dominate our office, which was basically just a room with tables so anything you’d say was out in the open, talking about their little loved ones.

    It made me think even if all older guys weren’t like my boss and his friends i’d never want to date one based on the stupidness coming out of their mouths. I know guys brag about their girls and side conquests but the PRIDE in their young girls, the disgusting terms used, the way they spoke as if their were the highest on the intelligence pole. It wasn’t as if they stood to gain anything from the relationship other than some wood.

    it turned me way off of being with older guys and in the end i realize a man is a man, is a man….is a man.

  • Perverted Alchemist

    Ding Ding Ding!!!!!!!

  • Rob

    I’m 45 and I don’t date women under 35.

  • jamesfrmphilly

    why i would not date a younger woman : no sense

  • Mia

    I have to say this came at the right time! I am 23 (with an older spirit), and the oldest I’ve dated was 37. A bald, sexy, hazel eyed, body of a god type man. Then realized he was as immature as the 24 yr old I dated. But the sex, amazing! Although he didn’t explore the southern region (which was the end all deal breaker) however, I love older men. I’ve always been attracted to guys at least 10-15 yrs my senior.

    I went out dancing this past weekend at an older club, the ages of men range from 35-70, no joke. But I met Mr. Thomas, a 55 yr old man, who distinctively told me “I can still fog up your glasses, make your hair nappy, and give you money to get it done again” I felt awkward, he’s old enough to be my daddy but I got turned on by the fact of him saying what he could do. Although I passed on his offer, I have to say that gave some points for the older men!

  • Mia

    Although we are young, we still raise the same questions. A woman’s intuition is a woman’s intuition no matter the age. That attraction isn’t always built on sex. Some men like younger women, not for the fact of making them feel younger or a control issue. We let them be who they are. If we get into a situation with dating someone older, they are set in their ways be it good or bad. We don’t go in trying to change them or shape them for marriage. If it gets that far wonderful but we aren’t going in for that. For some, dating an older guy is comforting, secure, a helper (not financially); for others its mere sugar daddy conditions. Personally, I won’t date over 40. After that it gets to be creepy and I do want more children.

    However, I do hate the fact that older women talk down on us younger ones that like to date older. We aren’t taking from your pool, but maybe shift gears a bit, try dating younger men & don’t pursue someone with red flags either. If he isn’t up to your standards don’t confuse yourself on “why doesn’t he have a phone or other material things”.

  • Penny

    I am 40, married and this is funny as hell to me. Don’t date our (women my age) rejects; they were left on the market for a reason. LOL. Try dating men that are 5-6 years older. There won’t be as much of an age gap, there’s a better chance that they are more in touch with things that you like (or they are at least more malleable than a typical 40 year old single guy) and less of a chance that they might have grown children living at home with them. I may be wrong, but I’m convinced that if you can get to them while they are in their 30′s (even late 30′s), they’re not as hopeless.

    This post makes me wonder what younger say about dating older women!

  • OSHH

    I can’t go older than about a 5 year range.
    I used to say 10 years but he’d have to be a certain kind of 47 yo for me to go there.

  • Mr. Man

    Very funny read. I see these guys all the time, and yeah know some too. Sometimes my wife would turn and say to me “If you ever…” but she never have to worry, throw-back vocab, patched jeans, ribbibed turtle necks, and or long sleeved no collar silk shirts ehhh noooo thanks. I’ve notice that many men my age (40) have greatly lost their fashion sense (if they happened to have had one), Based on their clothing choices I figured it ended in the late 90′s early 2000′s. These are the same guys who shop at Burlington Coat Factory/ Marshalls/ TJ-Max and Ross. – last years hotness.

  • OSHH

    IDK if you were addressing the author or the folks in the comments but let me say I personally don’t need a ton of options, readily available or otherwise, all I need is the right one for me. Anything else is a waste of time, knowing myself and that I do not desire a senior citizen, no offense. Now there is some reality for you :-)

  • ChezCerise

    Hey! I’m 29 and a VERY small section of my family still calls me by my childhood name.

    They refuse to call me anything else.

  • Erica B.

    As a 41 year old woman, men like the ones you described step to younger women because they know women my age aren’t having any of their foolishness. They feel younger women are gullible.

  • Angel Mia Feimster-Montoya

    Why are these 40-somethings so wack? I know 40 is older but these men mentioned in this article seem atypical of the actual 40 year old man. They seemed like they were 55 or 60. Geesh.

  • Telekendall

    My BF is 9 years older than me (I am 23) and it is probably the easiest relationship I have ever been in. I don’t have to worry about his insecurities as much, he doesn’t let me get away with the normal bratty behavior, and still treats me right. My parents like him now that they have met him and I think we worked bc we were friends before we dated. I have known him since I was 18 and he was never inappropriate and treated me like anything other than an equal. The only thing that I laugh at him for is periodically using the word tight. Other than that he dresses amazingly, has great taste in music, and while idk if I could date another older man b/c I know my man is special, I think that all should be on a case by case basis. But then I have always ascribed by the 3-6 year older rule in dating. My parents are 5 years apart.

  • Natacha

    You’re hilarious! Is 30 supposed to be the beginning of the end of time? In either case, no matter what age you are you shouldn’t settle for wackness.

  • Natacha

    I agree with you 100%. In retrospect, I was young and dumb and patient. Now. . .I’m not so young, not at all dumb and very impatient. lol

  • Natacha

    LMAO!!!!!! Your comment reminds me of a guy I met who bragged about his “late model” (old) Lexus and actually told me with a straight face: “If you work your cards right, I’ll give you anything you want.” (Yes, that’s a direct quote.) Mind you, this is the same man who alerted me to the Bargain Basement at DSW AND discontinued our conversation because he had to go and put a “sports coat on layaway” at Marshalls.

    Thank you, Mr. Man, your comment really made my morning. I can almost forget the pain of leaving my phone at thome. LOL!

  • http://@clnmike clnmike

    I’m surprised at number 6, I wouldn’t think that would be the norm.

  • hehe

    WTF I’m not even 30 something(not close) but how are you going to act like 30 something is old. What’s wrong with being picky? I hate how women are told what to do and what not to do in terms of relationships.

  • Jane

    Most likely this dude was the same at 20 and as the years went on he stayed the same which doesn’t surprise me. Don’t be mad cause you picked the cornball lol!!!

    My other half is significantly older than me and I don’t have ANY of those above problems. Maybe it’s just a rarity.

  • KKay

    I definitely tried it with the same thinking you had; I thought surely they were more together than the ones my age. I later found out that men are men; age doesn’t always make them wiser. The 2 older men I dated (One was 11 years older and the other was 15 years older…[sidebar: I know, 15 was pushing it, but I was being open minded,lol]) were still trying to get their lives together. I know everyone has different paths but you in your late 30s/early 40s should not be relating to me in my mid 20s; at that age I’m thinking you could actually give me some guidance, sheesh!

  • AJ

    RealityCheck – your statement was the most idiotic statement on this blog.

  • Mr. Man

    Just know that not all but many 40+yr old guys are mentally stuck in the Teddy Riley ‘New Jack Swing’ era of the 90′s.

    Whats the saying, pick your men like you pick your fruits and veggies, just stay out of Food 4 Less.

  • Mr. Man

    of course my comment was not directed at you I happened to hit your reply when I posted, sorry about that.

  • African Mami

    @ Erica B.

    CO-SIGN, 100%!!!!

  • secret ninja

    lmao at this whole post and all the comments!!! 7 or 8 years my senior is my limit, and i’m 28.

  • African Mami

    girl 9 years older than you is nuttin…he is just 32?! That is NOT old…..

  • Jared

    I’m not understanding. If the author wanted to “grow old together”, as she mentioned in #4, why the heck are you dating an older man? And as a reminder, the plural of anecdote is not data. Every reason you mentioned, save for #5, can be applied to any age group. Corny knows no age.

  • Erin

    I think that men that date women significantly younger than them (like you could be his daughter) aren’t all the way there, especially if he already has children your age, but that’s just me. A 1-10 year age difference isn’t that much to me, depending on how old you are, but I think the most I’ll do is 3-5 years.

  • mikey kun


  • Angie

    My boyfriend is 7 years older than I am, but I don’t really feel that is much of a gap. He’s in his 40′s, me 30′s. We get along great, he’s good to me and makes me happy. I don’t think age has much to do with it though. A while ago I dated a man who was 15 years my senior and he was worse than any 21 year old I knew. So, go figure….

    (The part about the throw back gear was funny though!)

  • Britt

    You forgot baggage. Older men have 10 years more dating experience and 10 years more of drama, relationships gone wrong, shoulda coulda wouldas and excuses. They are just as bad as women when it comes to carrying pain of past relationships with them to new ones. Smh

  • July

    This article is timely as this 60 year old man tried to holla recently (I’m 24). No.Thanks!

  • ljf67

    ROFLMAO! I don’t even like dating men my own age, and the whole “cougar” thing is played and tired. I can usually deal with a 3-5 year age difference up or down and trust me the up is pushing it – LOL!

  • kat

    I am currently dating an older guy. Honestly I don’t see myself ever dating a guy my age. They are so confused and I just can’t deal with that. The little mind games. I could never. So yea my next man will be an older guy.

  • OSHH

    No they are actually worse, at least women are able express their emotions a little more freely, thus being able to actually open up at some point again.

  • Adil

    This article is so shallow. I do not believe that one experience with a guy who has some medical and social issues is reflective of the 40+ or 50+. For that matter, the author should try and screen her dates before jumping into a relationship. Did she not see all the clothing and style issues until after the fact?

  • MovingOn

    I’ve dated a slightly older man once(I was 30 and he was 38)…it was alright, but to me one of the major turn-off was the fact the he was really into texting and sexting. I don’t roll like that so, I was disappointed that he really got a kick out of it. He even went as far as asking me to send him pictures of my body parts (which never happened). He also didn’t take my career seriously. I am a PROFESSIONAL massage therapist who takes my very seriously and he kept asking me if I’d ever given someone a happy ending. I know the age difference wasn’t huge but for him to be a little older he was extremely immature and slow…all at the same time…NEXT!!!

  • African Mami

    Oh mi gosh, can we have a post dedicated to those that have dated older gentlemen and it was not all disastrous. It was a relationship not defined by age, but rather by the maturity and chemistry of the involved parties?! Lawwwwd! It ain’t all that bad. Stop making it seem like it is a crisis out hurr.

  • anony


  • Telekendall

    Its still almost 10 years! But yeah he is great. I know he isn’t old but at my age. . . I had to convince my parents he wasn’t some creepy guy lol.

  • Simone

    What’s so funny about this is, the author sounds and acts like she is 16 years old. I understand the things that come along with getting older as I’m 49 myself. But I think back to when I was younger (in my 20′s) and I dated older men, I just wasn’t immature about the expectations.

    People get older, plain and simple. Didn’t you do any homework going into this. The article is shallow and childish. Grow up and mature….as you will someday find yourself on the receiving end of this list.

  • Simone

    You couldn’t be more right! Older men know what they want and are secure with that.

  • Reality check

    I agree. This is very shallow

  • Dwight Doc Little

    Yes as a older man I have baggage! Now what is baggage to you, children? Don’t you have them? I’ m a well dressed man and I turn a lot of heads from the younger generation! Ladies step your game up! It’s a lot of older men out here who will break your back if you underestimate him! Fashion, children, spirituality all of the above is yow you start the race! All of you
    that are negative grow up!!!!

  • Dwight Doc Little

    Yes as a older man I have baggage! Now what is baggage to you, children? Don’t you have them? I’ m a well dressed man and I turn a lot of heads from the younger generation! Ladies step your game up! It’s a lot of older men out here who will break your back if you underestimate him! Fashion, children, spirituality all of the above is yow you start the race! All of you
    that are negative grow up!!!! And yes, power to the V for the madness men go throughe!

  • thegirlwiththecrown

    Big ups to Thembi on this whole piece. That MJ Tumblr… Wow

  • Mr. Man

    Totally agree with you Simone.

    Don’t get mad because YOU chose to enter into relationships with these guys, I mean you didn’t catch a clue when you saw him rockin his Cross Colours coat and his British Knights…..

  • :(

    Mia…if he did NOT explore Southward, he is NOT amazing in bed. In fact, he is a bad f-k. You are young ;)

  • Nne

    I hold on to the adage that a fool at forty is a fool forever…if a man 40+ is single and chasing after girls half his age, it should serve as a red flag from the jump. Seriously, dating a man a mere 10-15 years younger than my dad – uggggh. I get it, people make mistakes when they are younger and may find themselves single much later in life – but why the need to date across the generations?

  • damidwif

    hell yeah what’s up…lol

  • lynette

    LoL!…The girl in the picture looks like she’s still in high school…just how Russel likes ‘em!…anyway I don’t think you’ve met the right older guy…my former boss was in his later 40′s or early 50′s…salt and pepper hair…and was FINE! I used to stare into his dreamy eyes and wish he was still single…you need to meet the ones with some swagger…not all of them got that…some have let themselves go due to a bad marriage…or a bad break up…others just don’t care anymore and expect you to date them just because….

  • LKJ

    You did not lie on that Hugh Jackman tip. If he weren’t married, he could get it 10 ways til Sunday

  • Laina

    Cute article. I question men when there is a big age difference. Like just because you can doesn’t mean you should. If someone is young enough to be the age of your little sister, why are you involved with her? And when the tables are turned and down the road, an older man is after your daughter, how do you think you will feel?

  • Alexandra

    Well I’m sure everyone has their own definitions of ‘old’. Anyone 10 years older than me is a no-go. I’m currently dating a guy older than me (by 5 years). So yes I would, but I don’t think I could go over 33. At one point I thought I would have no other option because older men approach me the most :-/

  • Blue

    Superficial reasons not to date someone. No wonder your single..

  • RealityCheck

    I’m sorry, but I’m still confused. 70% of African American Women are single. 72% of African American Families are single family households. But, black women still find the time to bash and make fun of black men…let alone black men that more than likely have their shit together at that stage of their lives. How is this logical, you obnoxious, self-centered, least desirable women?

  • PGS

    umm…Realty Check,

    where are you getting your stats?

    70% of black women are NOT single.

    According to Census data that number is more like 42%, and decreases with age (for example…by 40, 30% of black women are still single, which means 70% are married).

    The 70% number refers to children born out of wedlock, which doesn’t mean those women don’t eventually marry, so please stop with the scare tactics.

    This article struck me as simply a humorous piece. not a commentary on ALL older men. Stop taking things so seriously & laugh a little.

    Oh…and if we are so obnoxious & “least desirable,” why don’t you go comment on websites with women you find MOST desirable & leave us alone. K? Thanks.

  • TR

    Some of you may be taking this post too seriously. I took it as humor.

  • PGS

    same here. sometimes i swear folks around here don’t know how to LAUGH. everything has to be “deep.” smh.

  • chinaza

    The problem with dating significantly older or younger men is you (generic “you”) if you actually think “age is just a number” without the context of time/history and culture/experience.
    It’s like going to a beach and complaining about the sand.

  • damidwif

    i wouldnt be to concerned with providing facts to reality check. every opprtunity he/she can, he/she gets om here and says the same thing about 70%. * snooze*

  • Vee

    Personally I prefer older men. Just about every man I have dated has me at least by 5 years. The oldest I would probably date is someone 20 years older than me. I am 34. I have never really cared for men my age.

    Age is a number and I have met some older men who act like they are 5 & 6 year so it depends on the person.

  • Vee

    I agree some people take things too seriously.

  • Chantilly

    snap. snap.
    *standing up and waving my church fan*

  • Danielle

    All these dumb ass statistics about the percentage of black relationships failing make me sick. That is all.

  • linda


  • Timcampi


    I know right? Haha, I’ve been grave-robbing that ish since the fourth grade. He’s the perfect older gentleman.

  • GW

    Cute, humorous article. I’m a single 45yr old man and I can laugh at this, but I actually don’t fall into any of those categories. Seriously, I don’t. OK, you don’t have to believe me. LOL!

    I can tell you that you get all kinds at all ages. There is one truth: finding quality people is difficult. It comes down to confidence and character. Without those, there’s nothing.

    Good luck to everyone who is searching. :)


  • sunshyne84

    That’s why he needs you in his life….lol

    Mama gotta stop doing his laundry though.

  • African Mami

    @ Dwight,

    Uh oh! You stand up for older gentleman! That’s right.

  • ogre

    …..oh i love it, truly – although the enlarged wallet is desirable, the enlarged prostate constitutes a problem…..& i guess knowing “how to treat a woman” means to continue to cater to the princess fairy tale syndrome daddy started some 20+ years ago – never let go of expectations!! ;-)

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  • Aminah

    I’ve always dated older men. When I was single & in my 20′s I dated a man in his 60s. He was financially stable, a widower, and his 2 children were grown & gone with their own and he was going through his second childhood, so to speak. We had a blast racking up frequent flyer miles and doing whatever impulsive thing we could think of. Dating is supposed to be fun. It seems too many people are over thinking it now. Everyone you date is not going to be the one, but if you spend time setting silly goals & critiquing everyone to no end you’re missing out on the best parts. Go with what your heart wants and who makes you happy. The only warning I can give about older men is that if they’re well put together they may fall hard and fast and if you’re not ready to settle down take it slow.

  • KayPee

    I can say that I Love the “Old Skool” Gentlemen who has his sh*t together, so I don’t mind that “My Guy” is 12years older than I am.

  • AlesiaMichelle

    Dang… lol

  • AlesiaMichelle

    Couldn’t agree more. The guy I’m currently dating is 8 years older than me and I love it. He is past his 20s and into the more comfortable 30s…

  • Mz Monique

    Omg who told them my story… lmao

  • Trina

    This article has to be a joke right?? How shallow.

  • Little Birdie

    “I can still fog up your glasses, make your hair nappy, and give you money to get it done again”

    Wow, that lame ass pick-up line turned you on? Someone’s easy to impress…

  • Linda

    This article is hilarious. Max for me is 5 years.

  • Sunshine

    I’ve dated men over 10 years older than me. I’ll NEVER do it again. Let’s just say they turned me into a cougar…. lol

  • Trini

    The part about the meds had me rolling!

  • anonymous


  • Kema

    They probably were 55-60 and lying about their age. I’m 30 and tend to mess with the 40 range and havent had that problem.

  • Kema

    It is!!! Women go looking for older thinking it will be different when in reality your character is your character. Really immature men at 30 will probably be immature at 40 and 50.

  • Dr. Goddess

    This article is hysterical but then I had a great intro from Thembi, herself. I have dated older men and I was screaming laughing. You do have to be careful and definitely don’t assume that an older man is more mature. They SHOULD BE but I’ll be damned if I didn’t find at least a couple who were super immature (emotionally), even if they had solid, financial means. Otherwise, you can have fun. I admit that my experiences have left me more shy to date them, though. Hmmm… I need to think on it… but this article was great! Thank you, Thembi!


    You had no business snooping through his medicine cabinet. That was nosey and trashy. And require that he own a home? Can you say “golddigger”? Please don’t date any men.

  • Joan

    If he’s still single and over a certain age, he’s defective. I know it’s not nice to say, but here it is: If a woman close to his own age couldn’t clean him up and turn him into something, then he’s just stale bread. Ain’t nothing you can do to make stale bread less stale…same with old reject men. They just weren’t raised right and that is not the kind of man you want to father your children.

  • BlackCTzar

    WTF kind of cornball dude you was rocking with? All the issues you went through sounds like you was just dealing with a straight lame, LOL. Im very close to that dude’s age and me, nor any of my dudes, have hightop fades… hightop fade… in 2011??? Word? That’s ya life??? smh LOL Wow, get outta Kansas sis, LOL. Also, if dude was wild immature like you say, well sounds like a pre-existing condition, he would have been that way (or worse) if he was the same age as you.

  • SP

    I’ll say this about dating older men. I have no problem with it.

    My father is 10 years older than my mother, and they celebrated their 25th wedding anniversary earlier this summer. So I’ve seen first hand how such a relationship functions and can endure.

    I’m currently seeing someone who is 10 years older than I am. When I told my mother how old he is, she did mention positive and negative things to keep in mind if this relationship were to become serious/long-term, but, that it can work

    So am I ageist in my dating pursuits? No, not at all.

    I believe true love and a real connection can come in many different packages, even if it has to transcend a decade (or maybe two).

  • Vee

    Aminah I love your post!!!! You are right dating is suppose to be fun. It is what you make of it. Every date is not one size fits all.

    It’s what makes an individual happy.

  • CoCo

    You ain’t neva lied….it was funny. I was rolling on the throwback fashion and vocabulary…..there are always pros & cons dating older or younger men. Compatibility is key!!!!!

  • Catherine Rockshire

    Okay, done it. Dated older, and younger. In truth, men closest to your age, will probably work out the best. If you date younger, you wait for them to grow up, and than realize most people don’t! It is most likely that you will have more in common with someone the same socia-economic background as yours, even the same ethnic, religious background. This is why arranged marriages have been around for so long!
    Love is blind, lust is fun, but more often than not, our parents may (or may not) know what is best for us! Well, at least they try!!

  • Anna Renee

    Thembi is a good story teller! I guess that’s what she does! ;)

  • Essence Gant

    OMG!LMBO! My friend sent this to me because I was so stuck on dating older guys, just to try something new! It’s 12:05 am, I’m sure my neighbors are knockedd out, and I’m over here cracking up!!! This was very well written and very true!!

  • koka

    Amen sister!

  • Andree

    I am dating a man, and it so happens to be older than me. I am in my mid twenties. And he is in his early fifties. Dating older men is not for all women because of the age differences, etc.. You have to be very strong, secure, and grounded to be able to handle a guy this age and society’s point of bullshit(view) about this type of relationship. The guys worry about that more than us. They are always conscious of it, so it’s not easy reassuring a grown man that you don’t give a fuck about what other people think and that you’re happy with him. He’ll never admit that he worries, but when you know your man, you know your man.
    You were dating men with no style and assholes who refused to grow up. Age is not the problem, the men have a problem, they were idiots when they were young, they’ll die this way.

  • Janine

    I’m 20 right now and I’m falling in love with a 36-year-old man. I’m a Libra, he’s an Aquarius. We get along perfectly. He is loving and affectionate toward me, very articulate, intelligent, talented, artsy, and hilarious. We have an unbelievable attraction toward one another! I’m in college… so it’s definitely weird. He has two daughters, and is divorced. I’m still coming to grips with that. He definitely has some throwback vocabulary, but not that much. He’s handsome and confident, and is pretty socially active. He’s dated younger women before. Idk what to do with him; it’s not like my mother would exactly agree with our 16-year age difference… There is also a 32-year-old man that is interested in me, who is my friend at the moment (innocently). I’m tired of the idiot boys my age… And I only seem to attract men in their late 20s or early/mid-30s. I don’t look my age, either… I’m full-figured, and articulate, which gives most men the incentive to try. I shouldn’t really even be dating, even if I’m on the dean’s list. Anybody got any suggestions or comments? Am I crazy? Lol!

  • sasha

    I’m dating a man who is 12 years older than me and it has almost been 4 years. When I knew him, I was 22. We had lotsa fun dating, hanging out & so on. It was me who who made my first move because it was uncomfortabke for him considering I am way uounger than him & felt it was too good to be true.

    Though we had problem comprehending certains issues at the beginning, we eventually came out of it by understanding each other better. We are very honest how we feel, our thoughts and feelings. We are not embarrassed expressing ourselves without the fear of being judged.

    Yes, his dress sense is odd, his behaviour can be fatherly or he can be boring at times, I live him the way he is. I never change him for anything.

    For girls who would like to date an older man, my advise is mature, understanding & fun. He’ll love you the way you are & in return make him feel younger too. :)

  • Keith Walters

    LOL! This is hilarious! Sounds more like you picked the runt of the litter. This article is in no way fair to older men as its more a reflection of your character flaws in picking good men. Some how I don’t believe you could even pick a good man your own age. Further more if your whole outlook on dating is based around a man’s age, medicine cabinet, and fashion sense… you’ll be looking for a long time…lol! Here are two terms you should commit to your dating vocabulary…”core values” and “character.” Regardless his age or anything else…if these things are in place you would have completed your objective cause you will be in a meaningful relationship with a “man”…which should be your motivation in the first place. Momma needs to rebirth you again and start over….lol!

  • sarah

    I’m sorry but a lot of these issues seem to be a bit superficial. I think it’s time to look past wardrobe, hair and medication. Things you should of been thinking about before you went into finding an older man. I’ve been talking to a guy 19 years older than me (i’m 21 while he is 40) for five months now. Yeah, he’s balding and wears hoodies and the occasional pair of jeans with a whole in it but that doesn’t bother me. To be honest his personality and the connections we share make those things adorable in my eyes. I know he will pass before me and be popping pills long before i have to but i’m more than willing to hold his hand through the entire process.

    You should definitely consider those factors before you take the next step or even try to date someone older. I’m completely satisfied with our relationship. If you keep worrying about wardrobe and appearances in the long run you will never be satisfied. Those things don’t build relationships just destroy them.

  • serah

    I dissagree, I have recently started dating a 43 yr old, I’m only 24 and yes I understand many would find this discusting as he is old enough to be my dad. He however does’t look his age and certainly doesn’t act it. He’s funny, kind, caring and treats me better than any guy my own age has. I have never laughed so much with anyone bofore. He does have a daughter who is 12 and this doesn’t bother me at all, as he sees her often and I can see he is a great father which means alot. so many guys have kids they never see and I would never want to be with a guy like that. The age thing doesn’t bother me, however I have kept this relationship a secret and only told the people who means alot to me, because it bothers me that other people would be botherd by the fact and it’s none of their business. x

  • Shannon

    It sounds to me like the guys you’ve dated just have quirks that YOU dont like. The thing is, they may have hade these quirks when they were in their twenties as well. SOunds more like you were looking for reasons to despise dating older men, because none of your reasons are deal breakers. I find older men to (or in my case- man) to be the most attentive, caring, and sweet people to me. Younger men dont seem to work as hard for your affection, the just expect it.

    As far as health, the fact that he was being proactive in taking care of his health should have been a plus. Also that he was smart- not many men know the steps to correct prostate enlargement.

  • Zee

    Sounds to me like you were dating losers, not older men. I believe a man that’s past 40s will be in this area.

  • Trish

    I know exactly how u feel it took me 6months to tell my mOther. But we have been together for a year and a half. And i just recently told a group of my close friends and ya they had there jokes and laughs but at the end of the day there okay with it. It ia hard to share with other people but its something u do for love..!!

  • mg irizarry

    Ok, not sure if you’re still reading the comments, but this is MY OPINION. This doesn’t seem like an unbiased experiment, but more like a topic for you to write about, which if I may point out seems a little vain, and superficial. Either you have poor skills in choosing men, or simply put yourself into stereo-typical May/December relationships. The fact that you were turned off by the term “getting busy” points to your own immaturity, would you rather him tell you “let’s bone”. As far as the clothing situation, some of what you described sounds as if you jumped in a time machine and hit the dial for 1994. What established, professional “grown” man puts on patch-work jeans?? I’m sorry, but had you really been searching for love, vs. something to blog about I’m sure you might have found some fulfillment. I’m 34, and my husband is 13 years older. I have never felt so desired, satisfied, and cared for in any relationship. Maybe the real story should be how 25 yr olds play with people’s emotions and the write lack-luster articles about it. – G.

  • Abby

    I’m currently 19 and i’m dating a 28 year old. But I really love him and we’ve been dating for almost a year now. He’s obviously not 41 so he doesn’t act old or anything. Hell, he’s not even 30 yet! I think we’re okay. But, i think we’re about to get engaged. He’s worried about the aspect of a baby. He’s at the right age but i feel like i haven’t done much with my career yet. Help?

  • DK

    This article is hilarious! I was recently dating a 48 year old whose family still called him by his kid nickname, and his wardrobe was from the 80s and had no interest In updating it.. Which I thought would be very easy and an easy fix. Not so.. In fact, I even told him that he was cockblocking himself and he would laugh. I think the breaking point was that he just didnt have much experience since he had been married for 25 years and couldn’t have a real conversation. He was also very focused on what’s next vs. enjoying where we were at. Thanks for the laughs, this story was spot on!

  • DK

    You’re 19.. You need to live and experience life. You’ll regret settling down in 5 years when you’ve done nothing on your own.

  • BleepBloopBlop

    Dude, I don’t think it matters if you date an older guy, younger guy, man your age, or whoever the Hell. It seems to me like you generally have a problem with every tiny little thing. I thinks it’s awful how quick you generalize these men, too. Geeze. It’s not all older men who possess these traits. I got a quarter of the way through the article and thought, this is just a really superficial ass of a woman prattling on about how nothing makes her happy.

  • Lady_leo

    I just started dating a guy who’s 20 years older then me. I’m worried that he’s gonna get bored of me, I’m happy to hear that they’re other women out there who are in successful relationships with an older man

  • Hope

    I’m dating a guy who is 44 and I’m 20. Things are great, he comes with all of the “benefits” of dating an older guy and none of the problems.

  • Alex

    I am 20 years old in a relationship with a guy who though my same age is a lot like dating an older guy. He is serious and honestly I was too for a while but I am starting to feel like I need to find me right now instead of starting a life with someone.

  • Angel

    Wow ! I hope I don’t end up with a mature man talking to me like a hood! I would drop him realy quick. I am soooooo, curious to find out what it would be like to have a hottie mature boyfriend. I hope I find one that is intelligent, hot, hot in bed, mature minded, well mannered, honest, serious, being understanding, caring, non judgmental, ill tempared, educated, funny, Patient, non smoker, and allows me to be independent !!!! I hope these men that read this list is not going to think I have to high standrads. Well, I will ask god to bless me with a real mature hottie!!

  • Angel12

    The type of mature man that I am looking for i that take care of himself and stays in shape, and cares how he looks but not to much. And that dresses really nice and casual. Just basicly cares of his appearance.

  • stacy

    I love saggy old nuts…

  • Lena

    It seems you just dated the worst of the worst, girl. I will agree on the immaturity part though. I dated a guy 18 yrs older than me when I was in my early 20s and he was the most self-centered asshole I have ever met in my life. It was the worst relationshit I’ve had so far.

  • Ms Write

    I never had those problems when dating older men. The biggest problem for me was not having much to relate to with the guy and also long term plans. It’s pretty hard to build a life with someone who has already been there, done that.

  • Nini

    never had any of those problems the guy im dating is 17 years older. we have allot in common and actually think the same way. only bad thing is on lookers, people who i though where friends that went behind my back judging me and starting rumors, and family members who constantly worry about how society sees this kinda stuff. I at first never thought about dating older guys. but i just fell for him and it just happened. i cant force myself to not love some one who is clearly my type. age used to matter allot to me until i met him. our age gap still bothers me but i cant stop loving him.

  • GR

    What happens if you end up dating and marrying a man who seems to have perfect health and then ends up with ah prostrate issue at a young age? Would you divorce him? Shallow article and I don’t know any 40 somethings who talk 90s lingo. People evolve and keep up with the times. You mean to say a 45 year old attorney or surgeon would not do for you young lady? How shallow. Love knows no age or color.

  • Mike @ Dating Coach London

    Sometimes a may-december love affair can work, however, it is too good to be true. Chances are, the younger partner have ulterior motives for hooking up with the older partner which makes perfect sense why the former clings to the latter. Nevertheless, there are relationships like these that do work, in the real world, there are relationships like this that truly last. So, we cannot discount the fact that attraction can indeed happen between two people despite their age difference.

  • mary

    This is very shallow article.

  • Ada

    I love this article, thank you. Finally someone I can agree with. I dated a man eight years older than me and I had so much guilt I couldn’t offer him what a woman his age could. He’s almost thirty and I am only 20. I still wanna have fun while he’s thinking of marriage. I don’t plan on marriage till my thirties. So we don’t want to hold each other down. Although I’ve never dated a guy my age because they don’t like me and think I’m too mature. It’s frustrating! But I want to date someone my age once I’m ready.

  • Jessica

    I’m beautifully in love with a man 15 years my senior. I’m 23 and he’s 37 and it is by far the most incredibly satisfying relationship I have ever been in.

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