Oct 292008

If you’re in the mood for sexy, interesting flicks about hot younger men and sexy older women pairings, I’ll recommend my top 10 faves (as of 2008):

PRIME: Watch this one if you’ve ever thought, “I soooo don’t get the appeal of younger men.” You’ll get it after this. :) The movie shows the pros and cons. The pros, of course, are extremely delicious.

NOTES ON A SCANDAL: Posh British woman marries an older man and cheats on him with a soccer-playing Irish teen in her school. (Damn that kid is hot; fret not, he’s legal.) In addition to the older man - younger woman - much younger man trio, there’s a little older woman / younger woman crushing too.

HAROLD AND MAUDE: GILF sex. How could I not include this one??

HOW STELLA GOT HER GROOVE BACK: Believe it or not, I’ve never done the whole “vacation fling.” I’ve had a fling with a dude while he was on his vacation, but never during my own. Must. Take. Vacation. Soon.

Y Tu Mama Tambien: What’s better than hooking up with a younger guy? Hooking up with two at the same time. :)

Class: I used to be a huge Rob Lowe fan. That Andrew guy? Not so much.

FOOD OF LOVE: Instead of the older female teacher / younger male student stuff, this one has an older male teacher and younger male student. Hot. I’ve kinda got a thing for guy-on-guy action. Plus, I love Kevin Bishop. See him in this movie, then watch L’Auberge Espagnole. Hard to believe it’s the same guy. Good actor.

RUSHMORE: Damn, this “older female teacher and younger male students” stuff is a common theme. Male FUNKY BROWN CHICK readers, tell me: Did ALL of you fantasize about getting it on with your teachers when you were in school?!?

THE GOOD GIRL: This is probably my favorite Jennifer Aniston movie.

THE GRADUATE: Well, hello Mrs. Robinson! Gotta include the old standby, no?

* For the record, I soooo wanted to include ALFIE (Jude Law and Susan Sarandon), but I’m saving that one for a different post about the hottest interracial couples.

  60 Responses to “Top 10: Movies with Older Women & Younger Men Relationships”

  1. on the whole, crushing on the teacher, yeah, we all did. The number one reaction most guys have to the whole, 24 year old hot female teacher in trouble for banging 16 year old student is wanting to give that kid a high five.

    And, it was such a big one for me, that when I found out that the women i was dating was graduating to become a teacher, I married her. (There were other reasons, of course. )

    • I ended up doing naughty things with my crush/teacher 20 years later… He was 10 years older than me… We got really close over the past 3 years… and he died recently… He was married and we had an affair…

  2. Actually, we *didn’t* all have teacher crushes. If you saw the teachers I had, you’d know why I say that. >Shudder!<

  3. shadowboxer—helen mirren and Cuba gooding jr

    I will admit to some prior indescretions with older married women. LOL.

    I always thought cougars were fun. ;)

  4. I like The Graduate and Stella got her groove back. I am one who does date younger men. I used to date older back when I was younger. Now that I am in my 30′s I like men in their 20′s.. It is just where my head is at. Men my age don’t really want to do much. I like to go out and such.

  5. Maybe not every teacher but one or two for sure. The early years of high school,horny all the time, awkward and these wonderful young women authority figures. Bliss really.
    Real life, after school was much better. Older women still retained their appeal. Married ones too. Maybe married ones especially.

  6. Younger men are cute. I don’t know about long-term as they may wander once the novelty wears off. Still, they are nice to look at and flirt with.

  7. I had such a crush on my History teacher – one day as I handed in my paper at the end of the class, I kissed her on the lips. To this day, I cannot tell you why or how it happened, it wasn’t premeditated. What I do remember is that the class cheered, she tasted like cherries and smelt great (later, I discovered she was wearing Opium). I was promptly expelled, punished by my mother (read severely spanked) and sent to a strict boarding school.
    I don’t regret it and Opium still drives me nuts.

  8. @ Alexander: I think Sean Connery has a fun quote about the high five stuff. I’ll try to find it. :)

    @ Baba Doodlius: I know, right? We didn’t have hot teachers in my schools either? I had a crush on one the math teachers and my bio teacher, but I think that’s more because they were so brainy and really on top of their game. Smart men REALLY turn me on. Especially math geeks.

    @ dkzone: WHAT??? Helen Mirren and Cuba Gooding jr hook up in a movie?? How did I miss that one?!?! I’ll save that for the hot interracial couples post. :) By the way, I sooooo wanna know about the hot indiscretions stuff. You’re not the guy who sent me the email about fucking his best friend’s mom are you?

    @ Mahoganydymond: Exactly!! I think all energetic 30-something women should date 20-something boys. They’re able to keep up, so it’s fun.

    @ don: Hmmm … I get the impression you’re into: (1) eating fruit you’re not supposed to taste and (2) dominant women. :)

    @ starkitty50: For me, it works longterm too — as long as they aren’t TOO young.

    @ Patlabor: I *LOVE* that story!!!!!! :)

  9. I first began dating older “women” when I was a teenager. I was always told I was was an “old soul”. Because of this, the girls my age found me boring or confusing. I read alot about the one thing I was most interested in… girls and women. I was trying to understand how to get a girlfriend. The problem with my reading wass that I consumed literature about ADULT women, not girls. As a teenage boy, I began getting in the heads of grown women, by reading Essence, Glamour, Cosmo, New Woman and other women’s magazines. By the time I got to college, I was speaking their language but still often found it difficult to connect with sisters my age. So I tried women older. It was an easy fit. They were 5, 10, 15, 20 years older than I was. They were refined, full of conversation, great listeners, straight talkers, wonderfully sexual, although not always as creative as I hoped. (That changed after we would spend time together. I said I read alot! ;-D) They weren’t wishy-washy as so many sisters my age were at the time. They appreciated my intensity and passion. Only once did any one of them lavish me with gifts. After a few months of that, I put an end to the gifting. We were always friends first and I was interested growing that and the multi-leveled intimacy.
    Over the years, I’ve run into a few of them. Some married, some not. They have aged, gracefully, and remain beautiful, vibrant. When they’ve seen me, the sparkle of memory dances in their eyes
    when we chat. We embrace, laugh, reminisce and part as we met, like friends. My heart still flutters….

  10. of all… Stella was, 2 me, the best… all the Ladies out there are a turn on to me…
    from 32 and up… from 22 to 31 they have to decide which way is up.. then from
    32 on… everyone is so sharp….. but the most interesting ones are the cougars…
    they know exactly what they want… need…. and desire…. and they take no
    prisoners…… guys…. if you never, ever been with a cougar…. go for it…..

    lamesabassman…… it will change your life…..

  11. Have I shown you my list of eigenfunction solutions to the Boltzmann equation recently? :)

  12. No…. but please do Mr.D…. ’cause my brain needs all the help it could get….and do I have to stop eating the green M&M’s first….

    lamesabassman……. will try anything once…. as long as it dont tickle…..

  13. God bless this post.

    I had no fantasy-worthy teachers. Darn you, Catholic school!

    Fun fact about PRIME: there’s a scene in there from a restaurant off Bleecker, Sushi Mambo, that does worthy feats with mango and masago.

  14. I feel your pain….. having been to Catholic grade school and high school…. penguins….. to Brothers ( yeah, they were catholic 2…) they sure were nothing 2
    look at……

    lamesabassman…… ” Free …. at last…. “

  15. nope…never did that….thought about it once..okay twice, but what guy doesn’t think about that. LOL

  16. “I took the embed out because I CAN’T STAND audio and video clips that are set to autostart.”

    Massive thumbs up. Thank you for preserving us from the horror that is autostarting music/video.

  17. The Last Seduction.
    A great, hot, film.

  18. @ ROSEFOGG: Last summer, I went on a date with a younger man who said the same thing. Basically, I thought he was too mature for women his age, they bored him. Interesting.

    @ lamesabassman: :)

    @ Baba Doodlius: That’s hot. HOT!!

    @ Brenz: Glad you like it!! I’m gonna do a similar one for interracial couples. :)

    @ dkzone: :)

    @ medwards: I knew I wasn’t alone on that one. Seriously, autostart it’s probably my *biggest* online pet peeve. That and popup windows.

    @ Mike: Oooooh, haven’t seen that one.

  19. Now you’re just manipulating my affection for women of all stripes and types.

  20. well …. Brendan…… hmmm….. you have have not lived…. til you’ve been
    manipulated by women of all stripes and types…..” oh, MaMa … that’s where the
    fun is….”

    it’s a beautiful vibe…… and when they shoot that look…. yeah….. dat one…. well
    dont ya just …. kinda float…..

    lamesabassman…… am with floatation devices as I type….. mercy …..suffffah

  21. Oh MAN. I am totally renting the Good Girl now. Thanks for giving me something to put in my Netflix! Rushmore is also pretty awesome. And an amazing soundtrack.

  22. american gangster ….. the things you can do in this country…… maybe if Mr.Gov
    Ron B. had viewed this tome….. just maybe he could of dodged this fiasco …..
    no country for old men….. must see from the down stroke….
    first sunday…..a big pass….. bring back another friday… please
    anything by tyler perry…… you will have fun
    time bandits……. yeah, am dating myself…. but it is soooo cool

    lamesabassman……. at times like this…. Netflix rules

  23. How is Harold and Maude not listed here??? The greatest “older woman-younger man” love story of all time.

  24. Gore-gore!

    She totally did! Right before “Stella” and right after “Notes on a Scandal”.

    It’s ok, I don’t blame you, it’s such a great film, your adoration totally clouded your vision. So gooood….

  25. Oh yea… teenagers dreaming abt ther teachers… ya that i believe is common.. it sure did happen to me…
    i was 15 ans she was my maths teacher.. 28 ya 29 i guess, she was married but her hubby was away… was really beautiful. she has got fabulous body and i loved watching her skin thru her dress.. I always stare at her and she knew that i had a crush on her..

    Didnt happnd much..but on our sentoff party from the school, we were the one assigned to decorate the cornor room of the hall… it was late that day… and that was when i kissed her.. she was hot as an iron.. her hands went into my pants and my lips on to her 36C boobs… wooow..it was just 10 mnts..but i loved it….

  26. @ Dolly Shot: I love Rushmore! I saw Jason Schwartzman exiting my the same hotel I was staying in last Autumn. In person, he’s even hotter (and shorter) than I expected.

    @ Gore-Gore Girl: See Gore-Gore’s comment. :)

    @ Dolly Shot: LOVE that film!!

    @ Stanly: Ah, are you British? I love it how the Brits say “maths” instead of “math” :)

  27. great list!

    p.s. & the reader should be on this list… both HOT!

    topher grace (student applying to college) & laura linney(admissions counselor) in p.s.:

    kate winslet & HOT new german actor david kross in the reader:

  28. @Twanna…

    he..he..smart!! nice catch!! yup i am Brit :)
    and ya always attracted to older women..

  29. “Tadpole” was a coming-of-age story about a 15-year-old boy who falls in love with his stepmother, Eve and winds up with her best friend, starring Bebe Neuwirth, John Ritter and Sigourney weaver. It’s worth a look.

  30. I was so very naive.  Science fair projects were a big deal in my school.  I was working on a very sophisticated one involving experiments with soybean plants.  My science teacher was very interested in my project and invited me over to her house to discuss it.  She lived in school housing just at the edge of the campus.

    Back then, all the female teachers were very properly dressed and wore skirts and high heels.  After getting me a Coke, she excused herself to change into something more comfortable.  She returned in short shorts and a sleeveless blouse with the top buttons open.  She was also braless.

    She asked me if I wanted to get more comfortable, too.  She even offered some male gym shorts.  DUH…I told her I was comfortable as I was. 

    We chatted only a few minutes.  She had suddenly become much less interested in my project for some reason I could not understand.  I was so STUPID.  She was also the girl’s gym coach and very, very hot.

    I’ve hated myself for 43 years.  At least I’ve had a great fantasy to draw upon when needed or desired.


  32. [...] Top 10: Movies with Older Women & Younger Men Relationships | Twanna A. Hines @ FUNKYBROWNCHICK…. [...]

  33. Iron man is my favorite comic, and now the film is even nicer! Iron man 2 is coming soon, I can not wait to watch it! Me and my gal are very excited…

  34. I dated younger men. I found them to be interesting,not committed.

  35. In notes on a scandal when the husband is furious over his wife having an affair with the teen boy he says “we all want something younger”.  His wife looks to be 15-20 years younger than him so wtf is he talking about?? 

  36. [...] May/December romance as being perpetuated in the post just below this one, I offer up to you Funky Brown Chick‘s list of top 10 movies featuring a romance or sexual relationship between an older woman and [...]

  37. Dont you know what movie is this? he is a really young boy,  about 14 and he took an older girl to dinner in a restaurant, he touches her under table, then the got to his place and during sex she died, and the chofer helped the boy

  38. lol idk why, but i find myself attracted to older ladies like 25-28, while im 21, i’ve had this since childhood, when i was like 15, i was into girls like 19 and i’ve never dated a girl younger than me, the1 i have a crash on she 27 and got a kid, but still hot, im mature n got a body type older than my age, so its an advantage 4 me, n i avoid talking about age, i’ve actually got away wit that several times, but the moment they find out about my real age, they start feeling uncomfortable

  39. Does anyone know this movie name…
    The boy comes from a ferry to live with this couple who are seperated i think. The husband is a painter and often paints nude pics of woman and i think also sleeps with them. the boy fantasizes about the husband wife and she catches him. later they end up sleeping together. The woman has a small girl and the boy helps the woman take care of the small girl. In the end boy goes back to where he came from and woman also goes somewhere with her child

    • “The Door in the Floor”

      • I read and LOVED the book on which that movie is based!! :)

      • yo do you know this movie name……
        a boy over age 20 moved to a new place…where he spy on his neighbour’s wife who swimming nude………and later both talked and have an affair……her husband also is very rude having guns……eventually someone kills the husband and so… & i am not remember the cilmax……….

  40. I am a 51 yr old woman who is married and has a son in college.
    Recently i came to know a 24 years old distant relative who lives abroad.
    We have emailed and talked over the phone. The attraction is so strong yet subtle tha confuses me how i can explain it and digest the feeling. Both of us write and read poetry.
    A lot of our conversation is versed in poems. There isnt a hint of sexual innuendo from neither one of us. Yet there is much about longing to be beside one anothet, missing each other’s soul or just wanting to hear one another’s voice.
    He is 25.
    I feel sulky when he is not online. I feel sad when he doesnt write me.
    Funny thing is that I dont feel a tinge of guilt!
    What tje hell is this? I cant figure it out, anyone?

  41. Does anyone know this movie name…
    a boy over age 20 moved to a new place…where he spy on his neighbour’s wife who swimming nude………and later both talked and have an affair……eventually someone kills the husband and so… & i am not remember the cilmax……….

  42. Acurally a good movie about a nearly 18 year old student who falls in love with an 38 year old woman. There are some good erotic scenes and it is pretty realistic in the way it shows the young guy and his lust and lack of skills.. ha ha.
    Only issue. It’s made in Denmark and therefore it is in danish. Don’t know if you can find it with english subtitles.


  43. Hello Everybody,
    I am a 22 Yrs young man currently living in India. I really love hooking up with older women. I have had sex couple of times with women much older than me. I also love watch movies with themes related with older women-younger men relationship. I enjoyed several hollywood mainstream movies as well as movies from other film industries those were highly appreciated for that kind of storyline. I hope you will enjoy watching these movies.

    Check out these links provided with resumable mediafire host. Click on the following link and skip the ad. then you will get the original website.



  44. hii frnd
    i realy like that movies younger boy and older women hot..
    please tell me movies name i watch and feel hot please
     reply my frdsss..

  45. can u name d movie which is comin in youtube with the name aishwarya hot;boy removing the underwear of a woman

    • Hi Rahul, the movie about which u r talking is an italian movie Malicious (1973) its original title is Malizia . The actress was Laura Antonelli and not aishwarya rai. Nice movie.

  46. any name for the actor or actresses in d movie Rahul mention so we can find the movie name…. Rahul share the movie name if u got…

  47. whoa i watched notes on  a scandal aolne then watched it with my aunt wfter that v had very lusty sex my aunt is fat but she bomb my cock while riding !!

  48. [...] coming out of the woods. I had hypothesized that I would like to add some instruction on the topic. They can’t help it. This is sort of pretty. Attract men distance has been evaluated by many. [...]

  49. [...] notice the TV commercial for what men like in women breast? Keep them flying! I would like use what men like in women breast if there were no limits on what men like in women breast. I am suggesting what [...]

Share your thoughts | Get down with the funky brown ...