Confusion vs fear

[amc204]

Hi everyone,
I'm a 29 year old guy who is in a situation where I'm totally confused and don't know who to turn to or how to approach it.
There's someone who started at my workplace (not in the same office or building) a few months ago who I really like. I email her a lot about work things and she is always very grateful for my help and efficiency with getting things done (I basically look after some of the work she does). However I just can't bring myself to call (not email) her to see if she would like to meet up after work one day. She is heavily into volunteering and fundraising and was going to ask if she would be interested in a club I'm part of which does fundraising on behalf of charities. She has expressed an interest but the one time I asked (via email) if she wanted to come to one of the get togethers to see if she was interested she was unavailable (work stuff). I shouldn't be too bothered but I am and have asked her since (via email) if she would like to meet up after work again to see if she would be interested (even if I have a secret agenda) but had no answer. I know work email is not the best way and it sounds like she is always busy.
I had the whole of last week off because I had a couple of professional exams to do which I was busy revising for. Hopefully they've gone ok and feel overall they did but now they are out of the way I feel a bit empty and this situation has played on my mind while at work.
The background to all of this is that I've never been in a proper relationship and feel so weird because of this. I have had crushes in the past but never had the courage to do anything about it and when I do I always seem to get an instant rebuff. Maybe my eagerness and desperation is showing and I'm scared about doing the same with the above situation.
This is the one area of my life which bothers me so much. I'm in an 'ok' job although I'm looking to find something else, doing a professional qualification to hopefully progress in my career, have my own flat, parents who care for my well being (used to have a bit of an uneasy relationship with my mum but that has been mended and thankfully always got on with my dad) and I stay healthy. I have done 7 half marathons, 1 full marathon and plan to attempt a triathlon next year. From the outside I am proud of what I have achieved but my insecurities with my self confidence when it comes to relationships I fear is showing me up more and more as I get older. I am on a dating site as well but have not got to the stage of actually meeting up with someone.
I'm so scared of rejection and when people ask me 'whats the worst that can happen' my answer is another failure on the bedpost which I'm so used to that I fear thats what it'll always be for me. I'm actually scared of any potential comments I may get to this thread. So yes if anyone can help with how to approach the situation with the work colleague or how to stop looking so needy I would greatly appreciate it.
Many thanks everyone

[smackie9]

You can't enjoy life or have change in your life unless you are willling to take risks. Being rejected is just part of dating...but how can you even achieve your goal when you don't actually try. Just accept that it will happen, and move on from it to try again. Eventually you will win someone's heart.

Your eagarness and desperation, is brought on by your hesitation or fear to make a move to ask someone out....now remember that for next time.

[amc204]

Being rejected is just part of dating...but how can you even achieve your goal when you don't actually try. Just accept that it will happen, and move on from it to try again. .

When you say 'Just accept that it will happen' are you referring to the situation in the first paragraph of my post or just in general?
Thanks

[smackie9]

Rejection will happen in general. Your first post I would say she already has rejected you because you got too much like you said. Since you do see your mistake (being too eager and needy), instead of repeating this behavior, why not teach yourself some self control and not be compulsive. Learn to stop your self, back off, and give some space between interactions, and keeping the helpfulness to a minimum. You can't make people like you by buying them gifts, showering them with complements or giving so much of your time. We all have a need to be loved and accepted, but it can't be forced.

[AnnonymousMan]

First off, do not send her work emails about hanging out and all that. Trying to pick chicks up at work has never been my fort-ay but I know most girls are least likely to feel inclined if she is at work and busy or stressed. Don't lay things out so quickly, try to build friendship to a small level. When you email or talk to her act professional but slowly steer off into talking about everyday life. An example of steering is like... bringing up that you have to be somewhere, for example a rave (lol), and that will basically tell her something about you without her even asking. It is mental games basically, you are letting her get to know you without her even wanting to. This will peak her curiosity if you sound like an exciting and fun guy. Try this out and even talk about random shit with her, get at least the base level of friendship going. Then you can lay the game on her and ask her to go out or hang out sometime. A work environment, at least for me, has always been kept professional and I refuse to date people from work. But that is just me.

You sound like you need a little confidence. After you go through tons of girls and relationships your ability to jump into another one is much easier and you don't really find yourself questioning the 'how to'. If things don't work out with this girl, go ask as many girls out as you can on dates. Even if you fail horribly at first, you can never learn to ride the bike unless you practice.

Do not fear rejection.

[amc204]

Ok well I've got a work xmas do next week. If she is there then I plan to just talk and get to know her more and not rush into anything. Looking back on the communications that I've had with her in the past couple of months maybe I was a bit too forward so I'm going to take a step back. Our contact with each other is still very good natured and while it is mainly professional we still talk about things outside of work and what we've been getting up to which is good. I hope that this continues if I see her next week and not act like I have another agenda to see how I come across when I'm just myself. I'll look at the situation again after that. I feel a lot more positive about things in general and not just this situation. Maybe as I've got my exams out of the way and I can relax more but it makes me feel better about myself and hopefully that come across in any contact I have with anyone.