Like everyone else, I have a problem.

[nopersonaldata]

When it all comes down to it, I think I just really need to air some of this more than I need advice. I know my options and they all have the potential for problems. That said, I'm still open to hearing opinions.

I've recently come to the realization that I am head over heels for a woman who is in my life in a non-romantic role.......so far...
She's funny, one of the most caring individuals I've ever met and we both greatly enjoy spending time with each other. I would do pretty much anything for her and she's aware of that fact, though she rarely asks for anything. She's had a rough past with guys and while it's obvious she'd like to settle down somewhat, she's hesitant to make any moves. The real problems can be broken down into two parts:
1.) I'm a 26 year old male and she is 47. She's not only old enough to be my mother, she's a year older and friends with my mother. She's tried the 'cougar' thing once and couldn't do it, he was a 'pretty boy' with no job and difficulty keeping his dick in his pants. After that experience, she's obviously a bit jaded when it comes to a large age difference.
I've tried to up-play the age issue in my mind, in hopes of shaking these feelings, and it's useless, I'm absolutely enthralled by her and think about her constantly.
2.) She is my boss. This, in my mind is a much smaller issue, but still poses some problems. The friendship preceded the job and I took the job, part-time, as a favor to her (my day job keeps me quite busy, add in another part-time and some weeks are nothing short of exhausting) Normally, this wouldn't be an issue, I would just step down from the job if we decided to start a relationship. Unfortunately, the business would suffer if I stepped down and, whether through extra hours worked to compensate or through bad evaluations if she just let my responsibilities slide, it would negatively affect her.

That's really all I can say without divulging information that would make me uncomfortable.

[nopersonaldata]

Actually, I've changed my mind. I would like to hear some opinions or advice.
Additional data: she definitely has shining knight syndrome. Most of her previous relationships were with guys with serious problems. Moat of her friend could he described as broken as well. I kinda break the mold here. While not perfect, I like to think I have my crappy together. I'm 26, don't own, but have been renting the same 3rd row from the beach house for 4 years. I have no debt, never married, no kids, a squeaky clean criminal record.

My problems are definitely exacerbated by the fact that she's fairly sick right now. I've been worried to the point of physical sickness and bending over backwards doing anything I can for her.

I'm on mobile right now, will type more later.

[Sonrisa]

advice: when you are 36, she'll be a grandma.

[zertaag]

Opinion? Here's mine. If you love her, go for her. If you do not go for her, you are going to feel bad about it and no other woman is really going to live up to this prototype that she has imprinted into your mind!
Yes, she's much older than you, but love knows no boundaries. You are really not a young little guy who can't keep his dick in his pants, so although her 'cougar' experience before was bad, that shouldn't stop her from wanting a genuine, put together, nice guy despite his age!

You said that she's sick. Go to her. Continue to offer everything and anything. Take care of her. Make it known that you love, and care for her (in a non aggressive way, especially if you are reluctant to actually tell her of your feelings).

[Sonrisa]

Opinion? Here's mine. If you love her, go for her. If you do not go for her, you are going to feel bad about it and no other woman is really going to live up to this prototype that she has imprinted into your mind!
Yes, she's much older than you, but love knows no boundaries. You are really not a young little guy who can't keep his dick in his pants, so although her 'cougar' experience before was bad, that shouldn't stop her from wanting a genuine, put together, nice guy despite his age!

You said that she's sick. Go to her. Continue to offer everything and anything. Take care of her. Make it known that you love, and care for her (in a non aggressive way, especially if you are reluctant to actually tell her of your feelings).

yep, he is not a young guy at 26. most 26 year olds nowadays have the wisdom of a 40 year old men. oh wait, 40 year olds can't keep their dicks in their pants either. so what's the difference?

[zertaag]

yep, he is not a young guy at 26. most 26 year olds nowadays have the wisdom of a 40 year old men. oh wait, 40 year olds can't keep their dicks in their pants either. so what's the difference?

Generalizing an entire population based on your personal experiences hardly leads to valuable advice. You don't know that every guy regardless of age cannot control their penises. All I was trying to stress was that nopersonaldata has his head on straight and probably is nothing like the previous young guy that this woman was with. I wasn't trying to make a distinction between younger and older men.

[Sonrisa]

Generalizing an entire population based on your personal experiences hardly leads to valuable advice. You don't know that every guy regardless of age cannot control their penises. All I was trying to stress was that nopersonaldata has his head on straight and probably is nothing like the previous young guy that this woman was with. I wasn't trying to make a distinction between younger and older men.

how do YOU know that he is nothing like the previous guy?

[zertaag]

how do YOU know that he is nothing like the previous guy?

I don't. It was an assumption based on the tone of his statement and some of the things that he described about himself. I think that if he couldn't keep himself under control that he might have already made a pass at this woman. You are correct though, I do not "know" anything.

[nopersonaldata]

You said that she's sick. Go to her. Continue to offer everything and anything. Take care of her. Make it known that you love, and care for her (in a non aggressive way, especially if you are reluctant to actually tell her of your feelings).

I have been there, doing everything I can, from shopping/bringing her food to caring for her pets.

Her illness has certainly made it fairly clear to me that I can no longer just hold these feelings back. It's become rather clear, to me at least, that I would do anything for her. Obviously, I'm not going to push or say anything while she's still ill, that wouldn't be fair to either of us. I guess that gives me some time to sort through my feelings.

zertaag, your comment about other women never measuring up if I don't act on this hits the nail right on the head. I just have to weigh the possibility of ruining a great friendship against whether I always want to wonder 'what if'.

Thank you to those who have composed some excellent and helpful comments, I look forward to reading any further comments.

[MerryH]

If she were just some older woman you happened to recently meet at a bar/bookstore/whatever, then I would advise you to go for it. Why not. But with this woman, there's this whole...situation. It's good that you're going to take some time to sort through your feelings on this, so here are some things to consider in the meantime:

Since she's friends with your mother, how would this effect their relationship? How would it effect your relationship with your mother - would she be against it? She's your boss, so all things aside, it would be pretty wrong for her to date you. Does she even see you in a romantic way? She might almost think of you as a son, or something, and this is even more likely if you've known each other for a long time. Do you think that saying, "I would do anything for her" is healthy for you? Finally, and I'm not trying to minimize your feelings for her, but do you think your adoration of her might have more to do with her being sort of an authority figure, like how high school girls get crushes on their male teachers, for example?

I'm not necessarily trying to make any points here, I just think those are some questions you ought to ask yourself.

[deeblondie82]

Go for it! You seem wise for your age. I mean if you like her, she likes you go for it! You only live once I say

[nopersonaldata]

Excellent points Merry. As far as the authority figure comment, that is definitely not the case.
I'm pretty sure she is also interested, but has my same concerns.
I suspect that my mother would have some concerns, but be somewhat OK.

The boss employee relationship concerns me, but only because my quitting would cause problems. Otherwise, I would just quit if we decided to date. The income from this job is not critical.

[Incognito]

Well nopersonaldata the good thing about older women is that they typically know what they want and have their sh*t together (typically). That definitely sounds like the case here. If you feel that strongly about her then you need to talk to her about it. Sometimes to be the most sincere you have to just put your neck on the chopping block (i.e. come out with exactly what you feel knowing that you could be utterly rejected). If she has the same feelings that you do this will probably be a very positive occurrence. If you are also talking about having a lasting relationship with this woman you do need to SERIOUSLY consider the age difference (as Sonrisa mentioned). 21 years is a huge age gap. In just 10 years you'll be 36 and she'll be 57. At 36 do you think you'll be able to maintain a healthy relationship with someone who may not be able to keep up physically? Just three years after that she'll be 60 and coming up on social security collecting age.

You really have to be honest with yourself BEFORE you just into this. I was 18 dating a 36 year old woman. Believe me it was great and I would have married her, but a series of events happened that really made me wonder if I could handle what could happen and if I could handle the eventuality that she'd die before me. The answer, once I considered the situation without all of the emotional cloudiness, was that I couldn't. I ended our relationship and spelled out exactly why. It killed me, but I knew that it was for the better.

Maybe you can cope with the all of the things that will come along with a relationship with such an age difference, but you need to think about it now so as to save you both some heartache in case you cannot. A few more things to consider:

At 40 you will probably still be looking good and at 61 she probably won't be looking as good. Can you trust yourself to stay loyal?

In later years are you fine with playing the role of caregiver instead of husband? That may not happen, but it is a possibility given the age difference.

Your age difference will probably always be noticeable. Can you put up with the stares, judgements by and insults by others?

She will die before you do, barring illness that kills you prematurely. Do you think you can handle that heartache, especially since it will come sooner?

[nopersonaldata]

I'd like to think I could stay loyal. I've been doing a lot of thinking over the last few days and I'm fairly certain that I will be pursuing this as soon as she is fully recovered. She had a minor operation to fix the problem today and I was a complete nervous wreck. A mutual friend of ours took her to and from the hospital as I'm working a bit more than normal while filling in for her. We're both pretty close to this mutual friend and I'm pretty sure he's picked up on my feeling, but I think I'm going to confide in him and get his feedback.

[BackUpOrGetStng]

You should talk with her and voice your feelings. She will probably be hesitant, citing the two main things you pointed out in your OP. At that point you just say that if she doesn't want to give it a try, then you just need to distance yourself, and quit the job right then. It shows her that you're serious about what you're saying, and may cause her to give it some more thought.

There's also the chance that she says, yes.