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Help - I've had limited experience, and I'm attracted to an older woman.

Tagged as: Age differences, Dating<< Previous question   Next question >>
Question - (22 July 2009) 43 Answers - (Newest, 29 July 2009)
A male United States age 36-40, *olidus writes:

I'm 24 and attracted to a 36 year old woman. just recently moved to a new city. We were introduced by a mutual friend. She is incredibly attractive, went to an ivy league college, and has an amazing journalism career. We went to the movies the other day as friends had a great time then after she invited me to poetry discussion. We must've spent six hours together that day just hanging out. She even invited me out of town with her.

Our mutual friend told me that If I said to this older woman some of the flattering things I've said about her to our mutual fried that she would "Definitely fuck you" and that her "heart would melt"

I've only been with two women before so the proposition of pursuing an older woman is quite daunting. what do you guys think I should do?

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A reader, anonymous, writes (29 July 2009):

You "guys" didn't offend me personally. I was really speaking in generalities. I get sick of all the media hype and marketing and labels we all come up with to describe people we don't even know. That is a whole other topic though, don't get me started, the whole Bachelorette show for example, and real housewives of New Jersey with their boobies, makes me sick, so sick I had to watch it at least once, once was more than enough, thank you.

My brain hasn't turned into mush, not yet.

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A male reader, Danielepew Mexico +, writes (29 July 2009):

Danielepew agony auntRythm, please don't take this personally. I meant no harm. I am sure q1605 can speak for himself (he's grown), and I am also sure he meant no harm, either. I apologize if anyone feels personally insulted, but then I also insist that I had no particular person in mind.

By the way, did you notice that one of my posts does mention the "C" word, but I praise women of that kind?

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A reader, anonymous, writes (28 July 2009):

This this thread is quite humourous, but as a woman who happens to have had a relationship with a man 15 years her junior for two years, I find the term "Cougar" insulting. No one has a name for men who date much younger women, but have a name for the young chick, a gold digger.

Why is it always the women who are judged for whom they choose to lust after or even love?

Your 36 year old woman is one year older than my ex boyfriend when I met him and I can tell you she is not old at all and doesn't want to be made to feel old by a 24 year old who wants to "fuck her". She has an amazing career, a fine education and she knows what she wants.

She wants to be respected as well as lusted after and she wants love and affection and not necessarily in that order.

I don't know the temperature of your encounters, but she has been spending time getting comfortable with you and getting to know you and she wouldn't do that if she didn't like you and enjoy your company.

Surely you can tell if she is physically attracted to you or not? Treat her like and equal, and the next time you are sitting together watching a movie and you have had some conversation and the two of you feel a connection, then lean in and put your arm around her and go in for a kiss. The rest will take care of itself, or not...and then you will know if you don't allready.

Pay attention to the connection that you two have, if you are feeling something, chances are she is, too.

My guy and I met at work and were friends for a couple of months before we ever went out. We started going out alone without our work friends, as friends, and then it just became obvious to both of us that we were attracted and falling for each other. It was a rough relationship, but not because of the actual age difference. He had a lot of other issues and baggage that I did not as I was far more established then he was.

The relationship ended rather badly because he really started to just use me and lie to me about things. If you get into something with this woman, don't do that to her, always be honest with her about what you want and how you feel. We Cougars are one thing, we are too old for games and we don't have time for that shit, it annoys the hell out of us!

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A male reader, Danielepew Mexico +, writes (27 July 2009):

Danielepew agony auntq1605, you can send me a private message me if you need to :-). I need the wisdom.

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A male reader, Danielepew Mexico +, writes (27 July 2009):

Danielepew agony auntSolidus, I checked the YouTube video and yes, my strong disliking for Vince Vaughn notwithstanding (he got Jennifer and I didn't), I agree with what he said in that video.

Tell the cougar that you want a killer feline, not a small cat. Pun intended.

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A female reader, Tisha-1 United States +, writes (27 July 2009):

Tisha-1 agony auntOh no, Daniel! Don't ask Q questions like that! We'll NEVER get him off this thread! And thank you for the nice compliments *fluffs pink lifejacket and checks for black lipstick on teeth*, here's to youth, age, wisdom, and fun! *clinks wineglass*

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A male reader, Danielepew Mexico +, writes (27 July 2009):

Danielepew agony auntHey, I can play the role of "Pig Pen" too!

In case you don't remember who he is,

http://en.wikipedia.org/wiki/Pig-Pen

Tisha, you know you always look great. And, like wines, I am afraid you are "aged to perfection".

So does Eyes...

Oldersister is "older" for a reason, too.

q1605, give me your secret to keep all these fine ladies interested.

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A female reader, Tisha-1 United States +, writes (27 July 2009):

Tisha-1 agony auntWah! No fair, I want the bigger cookie! WAHHHHH!

Sorry, Solidus, every so often, some of us aunts feel the need to hijack a thread for our own entertainment. Well, q1605 attempts that with every thread, but this time, we've joined him. Hope you don't mind. There is actual advice buried in here, in all these posts, and we are rooting for you. Do you want to know the real reason why? We're living vicariously through you (okay, maybe oldersis isn't, but the rest of us are). That and we want all the dirt later....

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A female reader, eyeswideopen United States +, writes (27 July 2009):

eyeswideopen agony auntDaniel you get the biggest cookie and the biggest glass of milk.

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A female reader, Tisha-1 United States +, writes (27 July 2009):

Tisha-1 agony auntOh, and thanks, Daniel, for that nice comment! And to Eyes too, listen to the youngster Daniel! He knows a thing or two, despite his tender age. ;)

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A female reader, Tisha-1 United States +, writes (27 July 2009):

Tisha-1 agony auntI would be thrilled to be as young as 36 again! That's prime time for many women. Best shape, best career, best health... she's YOUNG. You're all making her out to be old but that's relative to our Solidus here, who is what, 24? He's young, yes, but he's not an infant. (You don't have any fetishes we should know about, right, Solidus?)

I've been working on getting back into my own primo shape, and I'm not doing too bad. I was contemplating my (still jelly) belly in the mirror one morning, and my husband said, "You'd look good in a bikini, for your age." THAT'S the qualifier I want gone, "for your age." I want: "You'd look good in a bikini PERIOD."

I'm confident she doesn't want that qualifier either. And frankly, Solidus, why should you put up with it yourself? You're a man, not a young man with grown man aspirations. You're a MAN!

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A male reader, Danielepew Mexico +, writes (27 July 2009):

Danielepew agony auntEyes, don't underestimate yourself.

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A female reader, eyeswideopen United States +, writes (27 July 2009):

eyeswideopen agony auntBeing an old broad I've gotta say that being with a young stud would probably make me feel older not younger I'd probably would just get out the milk and cookies...sigh

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A male reader, Danielepew Mexico +, writes (27 July 2009):

Danielepew agony auntTisha, better late than never. We all like you around here.

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A male reader, Danielepew Mexico +, writes (27 July 2009):

Danielepew agony auntCan Solidus tell her that he does not see her as an old woman, in line with Tisha's great advice (as usual), but as a young woman who will make up her mind and sleep with him? And, yes, that he does not need any help meeting someone else? That it feels like a group date so Cougar will evade Solidus?

Can you do that, my friend?

Oldersister, YOU HAD THE 21 YEAR OLD, did you not? The man is not waiting, and he was not I assume you were not telling him that you would find him a Little Sister who would not be as good as you.

I am sure good q1605 agrees with me: a Cougar is best, IF SHE DOES IT, not if she entertains the idea.

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A female reader, Tisha-1 United States +, writes (27 July 2009):

Tisha-1 agony auntI realize I am late to this discussion by the high school lockers, but I have a little nugget of advice I want to offer.

She sees you as a little kid right now because you are treating her as an older woman. She doesn't want to be considered an older woman. She wants to know that you think she is as hot as a 24 year old. That's the point. If you get all deferential and keep referring to the age difference, she's thinkin' "Alright, already, I KNOW I'm older than you. Now can we stop talking about it?"

She wants to feel like she's in her 20s, not in her dotage.

Start relating to her more as though she were in her 20s and therefore actually attainable (I'm sure q can come up with a more picturesque phrasing) than as some fascinating museum exhibit surrounded by lasers and alarms.

She wants to feel young, man, that's where you come in.

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A female reader, eyeswideopen United States +, writes (27 July 2009):

eyeswideopen agony auntSorry I hate it when that happens...just too impatient

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A female reader, eyeswideopen United States +, writes (27 July 2009):

eyeswideopen agony auntLet the old bitty do your leg work for you. Sounds like a deal to me.

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A female reader, eyeswideopen United States +, writes (27 July 2009):

eyeswideopen agony auntLet the old bitty do your leg work for you. Sounds like a deal to me.

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A male reader, Solidus  United States +, writes (27 July 2009):

Solidus is verified as being by the original poster of the question

Solidus  agony auntWow, this topic has ventured into very hilarious places. New developments have unfolded my older woman thinks I'm great but that I'm "Just a Kid" and now apparently she arranged for me to meet some "Sexy" half chocolate, half vanilla chica tonight. Immediately I thought of this...

http://www.youtube.com/watch?v=efnTDJy6zVw

So, I dont know how I feel about this predicament. My affections can't just be traded like an out of season Gucci bag. ;(

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A female reader, eyeswideopen United States +, writes (27 July 2009):

eyeswideopen agony auntHe's got a mother? LOL

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A female reader, eyeswideopen United States +, writes (27 July 2009):

eyeswideopen agony auntopps that's HOW

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A female reader, eyeswideopen United States +, writes (27 July 2009):

eyeswideopen agony auntHe's a wascully wabbit, but he knows hwo to make good gravy...just ask him...I dare anybody

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A female reader, eyeswideopen United States +, writes (27 July 2009):

eyeswideopen agony aunt...he certainly has a way with words doesn't he!!!!

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A male reader, Danielepew Mexico +, writes (27 July 2009):

Danielepew agony auntq1605, you're a friend.

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A male reader, Danielepew Mexico +, writes (26 July 2009):

Danielepew agony auntI agree with you, q1605. Actually, many of us have had our "whiffs" taken away the way you describe. None of us would even think about claiming "statutory rape" because we all loved it, did we not? We didn't see it as abuse, but as a wonderful chance, and we just couldn't have enough. It seems to me, however, that most of us did not need a warning that it wouldn't go beyond sex. If the woman needed to make that clear, I suppose the poster does not show this understanding in his actions.

I remember one movie I watched a long time ago whose title, unfortunately, escapes me now. It was about this pizza guy who slept with a married woman, a cougar. She spread the word and then he was sleeping with many other married women, all older than he was. I still remember the scene when he was sleeping with this incredibly beautiful Asian, and HE WARNS HER THAT THEIR RELATIONSHIP WAS JUST ABOUT SEX, AND THAT HE DID NOT WANT HER TO GET HURT. THAT HE HAD A GIRLFRIEND HE LOVED. Of course the Asian sort of smiled and said something like "I'll manage, don't worry". See my point?

My other complaint here is that I hate mind games, and it seems to me she is playing one on our poster. If she wants some sex, can she please be direct about it?

That's it.

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A male reader, Solidus  United States +, writes (26 July 2009):

Solidus is verified as being by the original poster of the question

Solidus  agony auntI'm not cold enough? Haha alright Danielepew what do you suggest I do. Give me the play by play.

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A male reader, Danielepew Mexico +, writes (26 July 2009):

Danielepew agony auntYour suggestion can be done, q1605, but I am afraid it can't be done by our friend the poster. He's not cold enough.

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A male reader, JSBach United Kingdom +, writes (25 July 2009):

I've changed my mind. Now I think you should keep trying with her. Gently, without getting too heavy. From what you write I get the feeling that she maybe wants you to try a little harder. She is now aware of how you feel about her, and if she really had no interest in a relationship with you,I think she would have stopped seeing you at least for a few days rather than making you pasta and taking you out for tea.

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A male reader, Danielepew Mexico +, writes (25 July 2009):

Danielepew agony auntBecause you seem to be her plaything.

For your own sanity, DEFINE YOURSELF what you want from this. Do not wait for her. That way, you give up the control of your half of the relationship. All those years she's your senior already give her a hell of a headstart.

To be blunt and honest, you're playing the fool because, who knows, you might end up sleeping with her. Yes, you might, a little kissing and fondling here and there... at the expense of being someone's plaything. Do you really need that?

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A male reader, Solidus  United States +, writes (25 July 2009):

Solidus is verified as being by the original poster of the question

Solidus  agony auntOh and she took me out to this famous little spot for ice tea and told me I was handsome in her car. I think its the little things like that that stoke my flame for her and simultaneously confuse me. I mean, you know I think you're sexy, you find me attractive...so why arent we doing this?

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A male reader, Solidus  United States +, writes (25 July 2009):

Solidus is verified as being by the original poster of the question

Solidus  agony auntToday she smoothly tricked me into making her breakfast and to make it up to me she just made homemade pesto and pasta for us. Then we drank some wine and watched some movies. She wanted to go out for drinks but didnt have any money on hand or feel like driving back.

I know there's an age gap but shes pretty much everything I ever wanted in a woman, but if she says not to have a crush on her I guess I won't and we'll just continue being friends.

The only problem I see with this is how attracted to her I am. The whole time we were lounging on the couch together all I could think about was how much I wanted to kiss her. When we're alone the sexual tension is thick to say the least. But its okay. I'll deal. Certainly not the first girl I didn't get.

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A male reader, rocknroll United States +, writes (24 July 2009):

As women get older and have an opportunity to survive on their own, they clearly will call the shots. Take her advice to heart, she is giving you your only warning and if you do not heed her advice, she will squeeze you like a bug. Women with this much power, self supporting, can be contemptuous if things don't go her way.

Treat her as a box full of playful kittens and you should do fine. She probably believes "enjoy it while you can, because love doesn't last forever".

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A male reader, Danielepew Mexico +, writes (24 July 2009):

Danielepew agony auntI am sorry to be the killjoy, but, here's my take:

Maybe she would like to have a little action with you ("a little action" meaning "a lot of sex"), but she does not want you to fall for her.

Or, she was flirting and does not want to go beyond this point.

In any case, take her at her word. Stay away, and let her chase you. If she returns (which I doubt), then be quite direct and ask her to speak her mind. If you don't get something very clear, the likes of "Oh, I was just flirting" or "Gee, we could be friends with benefits", then run for the hills.

At least you tried. Now is the time to wisen up. In the future, you will be approached by another woman like her. Ask her to spill the beans quickly.

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A male reader, JSBach United Kingdom +, writes (24 July 2009):

It's a real shame, but I think you should move on. If she has told you straight not to have a crush on her, she probably means it.

At least you tried. If you hadn't you would always be thinking what if.

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A male reader, Solidus  United States +, writes (24 July 2009):

Solidus is verified as being by the original poster of the question

Solidus  agony auntHmmm okay need some more input guys.

So I was out today running errands and had some time to kill. Passed by a shop and a guy offered me some lovely carnations so I bought some for this older woman since i knew she'd been spending the night over here (we're helping someone house sit). Anyway, so I gave her the flowers and she was really surprised and flattered. Then she reminded me how much older she is than me. Later she made us tea and before going downstairs told me not to have a crush on her.

But now I'm confused. Is she just apprehensive about our age difference? Or should I do like in that movie Hitch and "Try Harder" ?

What are your thoughts?

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A male reader, JSBach United Kingdom +, writes (23 July 2009):

Go for it, mate. It's your duty as a man.

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A male reader, Solidus  United States +, writes (23 July 2009):

Solidus is verified as being by the original poster of the question

Solidus  agony auntThanks for all of the good advice. I think I will casually follow this rabbit down the hole to see where it leads.

PS

I helped her carry some stuff from her apt tonight and she asked me to put the clean sheets on her bed cuz her arm hurts, well as i was putting the clean sheets on and bundled up inside them were her sexy black lace panties. I handed them back to her and she laughed.

Just wanted to share lol

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A male reader, JSBach United Kingdom +, writes (23 July 2009):

Go for it. 12 years isn't such a huge gap at your age. She seems to enjoy your company, so there's a good chance she would date you. And the worst thing that can happen is that she says no.

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A male reader, Danielepew Mexico +, writes (22 July 2009):

Danielepew agony auntGo with her. There's a possibility she wants you to be her toy. If you're fine with that idea...

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A female reader, alwaysreadyandwilling United Kingdom +, writes (22 July 2009):

alwaysreadyandwilling agony auntThis is cool,reminds me of an older chick who text teased me. We met on a dating site and had fantastic phone sex. I wasnt naive enough to believe i was the only one she flirting with. I know they where as young as 23 and she was 43. I dont know but she was coming to stop overnight with me. You know how it is. Argument with her fiancee and wanted what he wasnt there to do. Them older ones are ravers. More grateful and desperately hanging to their youth. Well she knows where i am. YOU WILL LOVE IT !

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A female reader, Emeline United States +, writes (22 July 2009):

Emeline agony auntAs corny as it may sound, do whatever your heart tells you to do. If you are truly interested give it a shot. What have you got to lose?

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A female reader, loves_giraffes United States +, writes (22 July 2009):

well giving it a try couldnt hurt. you will either like her or not. its that simple.

go for it

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