Do I say something?

Okay, so I'll warn any people who like to ask for a "shorter version" that this will probably turn out a pretty long read.

So heres the deal. I'm 27 years old, single guy, kind of a hopeless romantic in the sense that I sabotage any relationship I've had, and I guess I might be pretty fussy as I've no been in a relationship for a good few years.

Anyway, to the point. A collegue I work with is kind of my issue. To the point where If I could get her out my head or get closure one way or another I think I might turn out to be pretty happy.
I'm kind of the joker where I work, and I click with this girl really well, to the point that I know she has said I am the only person where we work that she actually gets along with. Which in a way I guess makes what is to follow that whole lot worse.

So about a year/ year and a half ago I kind of figured out that I had feelings for her, and now I'm at the point where I know I do have feelings for her and I really can't stop thinking about it, last thing at night, first thing in the morning style.

So, about her...Shes is 44 (Believe me I realise when I read that back that this seems slightly insane) So....Heres the things that make me wonder where I stand and what I should do.

For a long while now to see her looking at me randomly through the day at work, and then pretend to either be looking out the window, look away or do something stupid-kind of turn it into a joke, when I look up and see her looking. Even where if lots of people are in the office I will look and see her looking at me and then look away suddenly. Always comes over to my desk (other side of the room) to show me random things, photos of her decorating, ebay items, etc.When we are alone she will wheel her chair over to me and sits with her feet up on the desk connecting to mine and will sit and talk to me, so I guess shes pretty relaxed around me to be like that, I have never see her doing any of these things with/toward anybody else. She seems to treat me differently from other people too.Again, I have no idea if this is because she views me as a good friend or maybe she feels the same as I do.

Other things I guess I could add.


-Every christmas for the last 2-3 years we make eachother xmas cards, we don't do this for anybody else.
-She always sits and tells me things in her life, like problems with her other half and his son acting much younger than he is etc..
-When she walks by me and I am working she will pretend to hit me as she passes my desk.
-Like I said before, lots of looking at me, and if she saids something to other people, she will look over to me and laugh or see how I react to her.

...Theres lots of things, maybe some import things Ive missed out right now that would help.


So heres the reason I am finding myself on a forum asking for help, which I never thought I would ever do.

Recently she split up from her other half, Just dating, not married or anything, no kids etc.. And maybe I am crazy but I know her boyfriend/Ex pretty well, and it sucked that all the times in the passed that I have wanted to say something to her, I couldn't because I knew they were in a relationship and he would always come to me and tell me in confidence the problems they had, as a friend.

So in the last week I've realised a few things.

1) She has just split from this guy, and I know he still loves her etc..
2)I have no idea about timing and if I say something now if I put my foot in my mouth when she just needs a friend.But I am afraid if I don't say something now I might never get the chance to, or even worse, somebody else might come along and I will lose my chance when I had it

3)I kind of find myself getting really really jealous about her talking to other guys, it never is even the way she comes and talks to me or anything flirty, but I find myself sitting there like the green eyed monster and convincing myself or stupid things, which is pretty crazy, but I cant help jealously, and I guess nobody can or it wouldn't exist, right?

4)I know shes had at least one random guy ask her to go for a drink when she was still with her boyfriend. I got pretty hooked up over this cos I felt that she may have been interested, or liked the attention, even though when I did manage to ask her one day about him, she said he gave her his number, and shes never called. Again, it's not like this is any of my business anyway, just..it sucks to see when I feel like this about somebody.

5) Today I did a stupid thing, We were alone all day and had a laugh, spoke, she made me feel her ribs because I told her she looked like shes losing weight, she made me feel a huge bruise she got on her leg...etc etc... it was cool, but then I go and turn a bit, not moody, but I go quiet becuase I'm sitting and over thinking things, like I seem to keep doing. She asked me what was wrong, I said nothing, she asked me again in a playful way what was wrong, and I said nothing again. So...I don't know. I just get a bit caught up in thinking about things.

I just need help with what I do now, do I say something to her and risk her thinking out entire friendship was based on how I feel and fake? Do I say something and she freaks out and acts differently towards me because she is afraid I got the wrong idea? Do I say nothing and regret it later on?Do I just ask her out for a drink and see what happens? I don't know anymore.

And heres the kicker, the most insane thing about this, is I know that even though I have all these feelings for her, and bits of me thinks she likes me too, I wouldn't want to be with her. I know it sounds mental but I know it probably would be impossible, and it's not like I would even expect it or want it to happen. I just, really really wish she knew how I feel. Its crazy because I have lost count how many times I have wished and prayed she feels the same way as I do, now I just wish I would get a sign either way how she feels. I kind of think I need to know because its taking over my mind.I have never felt this way before about somebody and I know that if I knew or thought there was nothing there, I would never have ended up feeling this way, but I think its because of things that she does/we do around eachother that has made his blow up into how I feel, and maybe I owe it to myself to say something and see how it shakes out.

Thats that, like I said there are probably a million things I have missed out of this, but this is al I have right now, and I just really hope some of you who read this can give some helpful advice.

Thanks for reading.

Make it a lot shorter. Like one quarter of the length. From the specks that I did read my advice is that if you need to either make a move on her or just let it go.

You should be able to answer your questions yourself. Delicate situations like what u described can be thrown off by a random person's opinion, no one can know how deeply you feel for her but you. You have to tell her how you feel. I know what it's like to be in love like actually in love! Those feelings never fade, they might for a while but they always resurface, always. If you are really in love with her, tell her. One more thing, why would being with her be impossible? Thinking that way never got anyone anywhere in life! Anything is possible with a bit of positivity. Best advice I can give- follow your heart.

Make a move!

Any ideas how I should act on this without risking messing our friendship up? So confussed i appreciate any input.

It sounds to me that there is a spark between you that can develop in any direction you want it to. Once you know what you want, finding out what to do doesn't sound like a very complicated issue.

Do you want a relationship with her or not? Start by figuring our what you want to happen, then we can talk about what to do to get there.

There's no way to do it without risking the friendship. The truth is, it's NOT a friendship. You want more but you're just a pussy so you act like a friend.

Just a side note: You are saying that "it sucked that all the times in the passed that I have wanted to say something to her, I couldn't because I knew they were in a relationship and he would always come to me and tell me in confidence the problems they had, as a friend."

I can tell you are a man of integrety. That is an asset, and probably helps explain why she values you as a friend. Combine that with her being flattered by attention from a 17 years younger man, and I am guessing that she is struggling with the same dilemma that you are. I don't think this helps answer your dilemma, though...