Confused with an Older Woman...ADVICE PLEASE

So heres the info:

I'm 21 and shes 40 something w/ a son 2 years younger than me and widowed...

During valentines day I sent her roses and a letter confessing my feelings for her. She told me that I was very sweet and that she cried because of the nice things I've said about her, and then proceeded to tell me that she didn't deserve those kind words. The thing is, shes good friends with my mom and she thinks thats any kind of situation between us might screw that up. She never mentioned an age gap problem, but she did tell me that I will find the right person one day (do I take that as a big NO or is she playing hard to get). Now heres what buggs me... Before I even confessed my feelings for her our conversations were short with nothing spectacular but there have been a few occasions where we would trade complements. Now that I confessed my feelings she talks to me more and hangs out @ my house more often than not and we've grown to a point where we feel comfortable with eachother. In addition to that I'm helping her with classes required for her job training. So the big question is, is she just using me to get a better grade in her class or is it possible that she might share the same feelings. I mean she KNOWS I like her but shes avoiding that issue and at the same time is spending more time with me. She obviously hangs around me more, but I feel as if I shouldn't try to force her into a relationship fearing that I may push her away or offend her. Its just that i'm having a hard time interpreting these signals because I've never been in this type of situation with an older woman. She KNOWS that I have strong feelings for her, but isn't being clear about the possibilites of a relationship between us. I know she doesn't consider me just some young dumb guy given that I have a strong educational background. So whats the deal? Right now shes stressed out about her classes and needs my help to get her a passing grade and I was thinking about brining up my willingness to pursue a relationship after she gets her mind off of her up coming quiz. I can tell that shes not bothered by my strong feelings for her so should I take a risk and tell her that I want a relationship? or do I just help her and then let her go. Truthfully I really don't know how she feels about me. ADVICE PLEASE

First of all, no one here can possibly know what she's thinking, but I am sure she is flattered by your feelings and I can't imagine that she is too bothered by them or she wouldn't be hanging around your house. If she were really trying to discourage you, she would cool the contact.

But if she is really close friends with your mom, that could be a touchy situation. How close are you with your mom? If you have really strong feelings for this woman and really are considering pursuing them further, I would suggest that you have a heart-to-heart with your mom and gauge her reaction to such a relationship. Who knows? Your mom may be very receptive to such a thing and if so, that would probably allay some fears your lady friend would have to seeing if the two of you have something worth pursuing.

And my advice to your mom would be for her to have a very open mind on this matter. There have been situations where the child and the friend have decided to go against mom's wishes and mom has been on the bad side of her child and her friend. That is not pretty.

Hopefully, you feel comfortable in discussing the matter with your mom and with her friend/your lady and arrive at a friendly outcome for all.

Given that she's a friend of my mother, my mother already knows that we do hang out most of the time, but really isn't bothered by it. I'm assuming that if I did want to date her friend, she wouldn't care too much. The problem, I think, is with my lady friend. I'm assuming that she thinks my mother would be angry about the whole situation, but in reality she wouldn't be bothered by it much. So I figure If I do tell her that my mother wouldn't object to it then perhaps the situation would take another path. But here's another variable that I've considered. Optimisim is a strong factor in a blooming relationship, but if my relationship with this woman goes sour then the problem immediately extends to my mother. If my relationship goes south, of course her relationship with my mother will mostlikely head in the same direction. Therefore if you take the approval factor of my mother out of the equation, we're left with the risk of a doomed friendship between her and my mother. Because the situation doesn't affect the relationship between my mother and I, I'm willing to take a risk and see if it turns out well, but because my lady friend has more at risk with losing me and a long lasting healthy relationship with my mother if it does go sour then all this would seemingly be not worth the risk. In terms of game theory of course I would take the risk, but I don't know if she's willing enough to do the same given that she has that much more to lose. Logically it looks like a losing battle, but I know that science and love live separate lifestyles.

You're using the word "assuming" a lot. That can be dangerous.

If you are serious about this woman, the first person I would talk to would be your mother, to find out how she really feels. Be prepared to be surprised by her reaction. Typically, she'll be unhappy with the situation. She, like most mothers, wants you to be happy, but she won't think that happiness will be an older woman with two kids - and a friend of her's at that. She'll most likely wish for you a younger woman, without the "baggage" and who can give her grandbabies. Or maybe she'll support it - but you won't know until you bring it up with her. Either way, it's important to do this BEFORE something happens and that her friend does not look like she's been seducing you (as is often assumed, even though it is usually the other way around.)

You are 21. What do you want out of this relationship? It's hard to think that way at 21, but a woman in her position is most likely not looking for a f-buddy. Been there, done that, you know? And she most likely will feel the same about your situation - that you should be with someone younger who will be the mother to your children. It's hard for OW to believe that a YM wants anything more than a fling or can possibly be serious about us-at least the first time. There are some women here that prefer YM, but I fear they are the minority. Most OW are quite taken aback and find it hard to wrap their mind around a YM that is different from what they remember at that age. It takes a persistant YM to get what he wants.

Best wishes to you.

I find it possible for me to be attracted to older women due to the fact that I don't plan on having any children at all. The profession that I'm in won't allow me to be a close father to my children so I figured that I'd spare the drama and not have any. What I want with her is a normal relationship. Travel the world, watch a movie, go to dinner, ride a hot airballon, blah blah blah. I'm not looking for an F-buddy. I have so much respect for her that all I want to do is make her happy. Spending time with her simply makes me good. At 21 I've accomplished more than many people have done in a lifetime. So if age is the problem then I have no control over that. Its kind of a bummer when I've worked so hard in life to get to where I'm at and something like age that I have absolutely no control over screws me in the end.

I can understand your frustrations, I've been there too.
I've dated older men and waited for them, thinking that
they feel the same, but it got me nowhere. My mistake was that
I just keep hanging around and not confronted them because
I was too scared to rock the boat, or in case I scare them away.
My suggestion to you is just that maybe you can ask her out to
a nice place (dinner or coffee time) and ask her about her real feelings
towards you, regardless of what others think. Maybe you can re-
assure her that it will be okey whatever she tells you, you can handle
the truth. I know sometimes, it takes a lot of courage to do this, but it's
better to know sooner than later (I think). It will save you heaps of time
and heartache.

Take it easy :)

-----------------------------
But a woman's chief discontent is not with her political, but her social and particularly, her marital bondage.
Elizabeth Cady Stanton 1869.

So heres the info:

I'm 21 and shes 40 something w/ a kid 2 years younger than me and divorced...

During valentines day I sent her roses and a letter confessing my feelings for her. She told me that I was very sweet and that she cried because of the nice things I've said about her, and then proceeded to tell me that she didn't deserve those kind words. The thing is, shes good friends with my mom and she thinks thats any kind of situation between us might screw that up. She never mentioned an age gap problem, but she did tell me that I will find the right person one day (do I take that as a big NO or is she playing hard to get). Now heres what buggs me... Before I even confessed my feelings for her our conversations were short with nothing spectacular but there have been a few occasions where we would trade complements and mildly flirt. Now that I confessed my feelings she talks to me more and hangs out @ my house more often than not and we've grown to a point where we feel comfortable with eachother. In addition to that I'm tutoring her and helping her with her math classes required for her job training. So the big question is, is she just using me to get a better grade in her class or is it possible that she might share the same feelings. I mean she KNOWS I like her but shes avoiding that issue and at the same time is spending more time with me. She obviously hangs around me more, and flirts more with me but I feel as if I shouldn't try to force her into a relationship fearing that I may push her away or offend her. Its just that i'm having a hard time interpreting these signals because I've never been in this type of situation with an older woman. She KNOWS that I have strong feelings for her, but isn't being clear about the possibilites of a relationship between us. I know she doesn't consider me just some young dumb guy given that I have a B.S in physics and in Biology, and that I'm currently attending Med school. So whats the deal? Right now shes stressed out about her classes and needs my help to get her a passing grade and I was thinking about brining up my willingness to pursue a relationship after she gets her mind off of her up coming quiz. I can tell that shes not bothered by my strong feelings for her so should I take a risk and tell her that I want a relationship? or do I just help her and then let her go. Truthfully I really don't know how she feels about me. ADVICE PLEASE

DiceRoller, according to the info that you have given here, it sounds like she is playing hard to get, why else would she spend more time with you and flirt around with you? Sounds like she is enjoying the attention and waiting to see if you can take it to the next level. Also, stop having the mindset so much on getting her into a relationship just have the mindset of "seeing where this goes", and take things one step at a time. This is advice coming from someone who has been there and done that.

I guess I should see where this goes rather than wanting an immediate relationship. Thus far things are going great and we're getting closer and building up trust and comfort between us.

You so dead on right, I most CERTAINLY was NOT looking for a younger man! He had to be quite persistent to win my heart. I know several women that are married to younger men and ALL the younger men chased the older women, not the reverse. My advice to this young man, I think she is interested, or she would have RAN in the opposite direction, not started hanging out more with him. I do understand her hesitation because of her friendship with his mother, that would have caused me serious pause also. As most have advised already, talking to the mother seems the easiest way to clear that up. He mentioned that if there was a break up, that it might cause problems for the mothers friendship with this woman, not unless it was a really nasty break up, in which they pulled her in to. Break ups dont have to be nasty. Some people actually end up as friends. He should not add to her pressure right now. When her stress level is less, bring it up again, when they are more and more comfortable with one another after spending more and more time together, nature will take it's course, if there is chemistry there.

i really liked my husband before we got romantic, he would come over, i would be working in my nightgown, we would plop on my bed a few times and he would tell me about his latest problems with his girlfriends, i was more natural with him and the thought of being romantic was just not there. we knew eachother for months (nearly a year) and we were standby buddies for the weekends.

until he told me how he felt, then i was like a deer caught in the headlights.

dont assume she is putting two and two together, i went from having my buddy to getting an admirer. as soon as he became an admirer, i freaked. i stopped hugging him and touching him (platonically) and thought EVERYONE was staring at us.

she may not be getting it, maybe its time you left her in on your little secret.

You're intentions seem genuine, so just hang in there. It sounds like she's warming up to you. They always say a strong friendship is the best foundation for a relationship. It sounds like you really want a real relationship that will last...the more time you take to get to know each other and build your friendship, with her, the greater the chances this relationship will blossom and last.

I am 46 and I'm in a situation where I have become friends with a young man who is 26. We've been getting closer and involved in some projects together. It's very nice, we like each other, but I can't really tell if his feelings are platonic or if he is interested in more. Sometimes I think he is, but other times, I think not or perhaps he just doesn't know or perhaps not interested in such an older woman. In any case, I wish my guy friend thought like you! :D ....GOOD LUCK!

I wouldn't say she's playing hard to get -- like Peachy said, none of us can see inside her mind so the best course of action is to assume less and ask more.

I am 40 and my husband is 24 (3 years older than my son). When my husband first began flirting with me, he was 21. When he first suggested a relationship, a million voices in my head screamed, "ohhh nonononoNO!!" but one tiny voice thought, "well... why not?" I turned him down, although it felt bitter sweet and I was certainly very flattered. He asked me why not. I gave him my reasons (primarily age gap related) and he said, "Oh that's all? Then I'll just wait -- you'll come around." And he was right.

For some of us -- many of us, really -- it's a little scary, allowing ourselves to become vulnerable by getting involved in what is largely considered an unconventional relationship.

I finally did come around and I am SO glad!

My advice to you is to talk to your mother and see how she responds. Then, after one of your tutoring sessions, bring your friend to this site. And then? BE PATIENT.

Good luck!

since I've been hanging out with her, we've been opening up more. But the thing is, that she just thinks the feelings I have for her is just some sort of infatuation and not real. How do i prove it to her that this isn't an infatuation. I sincerely like her, but she doesn't believe it. What the hell do I do? She tells me that she's not bothered by the age gap, but at the same tells me that doesn't share the same feelings. THEN WHY HANG OUT WITH ME?!?! I throw her complements and she blushes and giggles all the time. I asked her if she wanted me to just give it up and she says, yes. I'm almost ready to throw in the towel, but at the same time I want to try and win her heart. I mean shes with me more than 4 times a week and we talk on the phone almost every day. Then she gives me some crap about how she doesn't feel the same way and wants a good reason why I have such strong feelings for her. Its really killing me and, I don't know how to deal with it. I can't just say, I GIVE UP and quickly get rid of these feelings. The situation for me is just so complicated and confusing. Do I throw in the towel or keep at it? she tells me shes not offended or won't be annoyed if I won't give up...what the hell does that mean?

THEN WHY HANG OUT WITH ME?!?!

Maybe she doesn't realize how she feels yet. Maybe she'll decide one way or another once you throw in the towel and you may find yourself being pursued. *shrug*

I agree that she may be playing hard to get, whether intentional or not.

When my boyfriend began pursuing me we had never even met in person...he worked relentlessly to convince me that I should give him a chance despite our 13 year age gap and over 4000 mile distance apart. So I flew to meet him after six months of telling him it would never work out between us, despite having been online friends for two years and being somewhat smitten with each other already.

Turns out that I was wrong!

We met in person in November 2004 and had subsequent visits, and we're still together and happy.

As I said, it may take throwing in the towel, yet remaining available, for her to realize how she really feels.

DiceRoller, according to the info that you have given here, it sounds like she is playing hard to get, why else would she spend more time with you and flirt around with you?

She could just want company and consider him a friend.

....could be she's just loving the attention and the ego boost.

I don't mean that she's a bad person or anything, but who knows, she could have lost her confidence somewhere ( perhaps from a previous bad relationship) and to have the attention of a keen young man is very flattering.....

Just my tuppence worth.

i dont blame you for being confused, she does not feel the same way about you but does not mind if you keep persuing her, that makes no sence.

well she asked the question why you care for her so much, did you answer? ask her "straight up" why she does not see you in the same light.

if you get a straight answer then you will know how to proceed.

She's probably confused because of the age gap, the fact that your mom is her friend, and also because she may not necessarily be looking for a serious relationship. She's 40, with 2 kids, divorced, in school. She may be enjoying her freedom and not be in a rush to get attached. So there are most likely many reasons she is hesitating. You might want to use some reverse psychology at this point. You've been coming on real strong and she has gotten used to it. She claims she doesn't feel the same as you. Well...the best way to find out if she means it is to call her bluff. Start limiting the attention you are giving her or perhaps stop it all together. See how she responds. This way you'll know whether to drop this whole thing and move on. :)

One other possibility that hasn't been discussed on this board, what if her last relationship went bad. Was it a bitter divorce or breakup with her boyfriend?
Perhaps the word relationship is like fingernails on a chalkboard, just don't bring that up any more, take some pressure off.

Do you overextend your stays with this woman? Remember not to stay any longer than an hour for your time together and always end you interaction on a high note. If she is interested in you and feels comfortable around you, and you leave her wanting more, then she will seek you out.

Since you have trouble gaging her interest and there is no "relationship" in the works, how about exploring life with other women? If she asks you to help her with her math problems, just don't be so quick to come over to her place or have her come over to yours. The word "relationship" may be scary to her if her last experience was bad.

Remember to sometimes tell her that you have other plans. Don't do that all the time, but sometimes. Maybe she will be curious and ask if these plans are with another woman. Maybe dating another woman will get her a little jealous. A little jealousy could be a motivator for her to want to take things to the next level with you, or give up on you entirely (if she's not ready for a relationship).

Focus with her on activities that she enjoys. It is about her. If you do three things that she likes, perhaps she will have a good interaction with you and want to take things to a new level. Don't ask what do you want to do....that would be kind of weak.

If she's into arts and crafts, then seek that out, sometimes they are listed in the newspaper. If she is into art galleries, take her there. If she's into shopping, go there. If she's into dancing, go dancing.

It is a hard lesson for a young man to learn to lead a woman, not let the woman lead us. Don't be controlling or overbearing, don't ask her what she wants to do, by now you should know her favorite activities.

Also, don't be so predictable, but remain in control of your emotions.
Predictable guys are boring.

I can't help but feel so stupid. I hold lectures in rooms of 300 physicists and mathematicians, and they humbly respect my intelligence any my methods in proofing. Im a mensa member with a 163 IQ, but with this woman its like I'm a dumb kid who doesn't know jack shit. She keeps telling me that I should find someone my own age. The thing is that I don't want someone my own age, I want her. When it comes to academics, sure she respects my opinion, but when it comes to relationships she doesn't trust my words. She keeps saying shes not worried about the age gap...YEAH RIGHT!!! she keeps telling me to find someone my age, but for me NONE of them are intellectually stimulating. I don't find their beauty the same as an older woman who can teach me so much more about life. She says she doesn't see a future with me, But I do. I seriously don't want to fall in love with her because I know I'll get hurt. I've been working with numbers all my life and it seems that this time numbers are the one kicking me in the ***! She's just so beautiful, and sweet that I don't want to give up on her. I hope shes not a gold digger...my friend said if I bought her something extravagant then she might change her feelings. This was also based on Game theory, Extravagant = financial security, risk assessment, Thoughfulness, and being SPRUNG. that was the simplified unquantified version of it. Sometimes I wish I weren't me. Do I deserve this?

I think she is using you for her own self esteem. If she wanted you, by now she would have let you know. If she's a game player you need to be careful, you sound genuine.
Just leave the subject alone for a bit and see what she says, she might just start persuing you instead. :)
Good luck.

I think you should back off a bit and stop being so 'Available'.....

Yeah, I KNOW....that games thing again......but stuff it....

Plus, I read somewhere that if you want something that bad.....when in doubt....Lean out....

This means.......back of .....and I dont mean it in a horrible way.....

I think that she has feelings for you, that she is possibly testing you....that 'she'
doesn't want to get hurt with a younger, inexperienced, blah blah guy....

....but to me....You sound pretty 'on to it'.....your writing style is very easy to read....hell, I wasn't even going to post here....but I found myself just reading and reading.....

I would like to meet someone that could say ....."I want a relationship with you".....Everybody seems so bloody scared these days....or is it just what Im attracting.....


Enough sob storys.....and try this Dices.....

Forget about the fact that she 'needs' your help.....what about you?

What about 'your' needs?

Be unavailable....busy.....other things to do.......Just for a little while....

Dont see too much of her.....She has to make a decision, one way or another....You have laid it on the line.....Now its 'her' turn.....Because whilst you are constantly in her face.....she doesn't really have to take any action does she....

.........and Ive a feeling that she really 'could' like you......so give her a chance to show it.......and if not....well, then you haven't really lost what you didnt ever have.....have you!!!

Well, thats what 'I' think anyway......

OH.....and the mother thing.......well, you could analyse it until the cows come home....but it wont go away will it......but will your feelings for this woman.....go away that is???

.........good luck ;)

Do a search for David DeAngelo and Double your Dating.

Subscribe to his free newsletter and you will receive advice on how to illogically attract her.

You know I could be as idealist as most everyone here, but most are in a relationship and you're not.

What if, what if, what if....are really not going to get you there.

But "what if" she's really not as into you as you are into her and she jsut wants your friendship and nothing else. I mean really, how many ways can this woman tell you NO!!

Look we tell men all the time that if a woman says NO, she means NO, not maybe, not later, not when the cows come home...NO means NO. She's telling you, she doesnt' feel the same way about you...get a clue.

Stop getting in her face and find some other direction. As much as we might want this relationship to work for you, you have to respect what she's saying. Let's break it down:

1. She doesn't have an issue with the age gap, why won't you believe her on this, is beyond me.

2. She's in a bind with her relationship with your mother, as she should be, there are too many men out there to wreck something that's obvious important to her, even if its not important to you.

3. As Peachy says, we can't get inside her head, but it sounds to me like she's trying to figure out a way to not hurt you and you're not listening. Don't listen to us, listen to what she's saying.

4. She's telling you she doesnt' feel the same way about you...and she's told you several times, how much longer do you think you will keep hitting your feet aganist the bricks, you gotta put your shoe on sometime buddy, that's going to hurt.

I agree with Tink...you've told her how you feel, not back off, if you spend any more time with her than you need to, then you know what, you're the one whose going to hit the dirt if she really means what she says. If you want, you can give it one more college try, sit her down and tell her that you're serious about having a relationship with her and you feel that its going to work and you want to know how she really feels because from here on out, you're going to back off and give her 2/3/4 weeks to think about it and come up with a response...but you will not continue to hang out with her while your feelings if your feelings are not going to be acknowledge or return.

Dude, its time for some self preservation, some backbone and alot of self respect. There are ow out there who are open to an agr, even on this website. This whole AGR thing, doesn't have to be that hard, not anymore.

Sure you can chase her till the cows come home, its work for some, but not many, yours is no guarantee. What you can guarantee is to give this woman the final big push and then stand back and let the chips fall however they may. She's a big girl, she can handle it, but you, who has more invested in this relationship than she does, may not.

Paris

She is giving you mixed messages by saying NO but hanging around with you more. Maybe it is just the flattery she wants. I agree with what so many others have told you they think: back off, take her No as No and see if she changes and shows some interest in a relationship. She shouldn't use you to bolster her self esteem and tears your down.

I'm sure he's running for the door. But I know the girls have your best interests at heart. Love, whether you have a 163 IQ, or an 80 IQ is hard stuff. And the baddest thing we all do is Wish others into our lives when they are actually not there in truth and feeling. And we ALL DO IT!!! So don't feel bad. Many gave you good sound reasons why they think she's just not interested in anything but a friendly social relationship with you. Please, if you take anything from my post today, see that for the gift that it is. BF's and GF's come and go, but friends you tend to keep for a lifetime!!!

Ali

I'm giving up on her. shes really driving me nuts! Once she passes her classes then I'll just move on. I don't need this crap!