Too shy to ask her out/make friends

Although I'm way more confident then I used to be. I've worked on it so much the past few years, I've found in some situations that I revert back to being stuck. Situations such as an extremely attractive girl that I'm really interested in (why I try not to develop interests right away now), or just in large meetings.

What gets me down is when I do explain how I feel to people. They simply just pull out lines that are meant to comfort me but not understand me. They don't seem to believe I can be shy or have self-esteem issues.

I guess frustration I'd building up because I can't ask someone out at work who I like but don't talk to much. We spoke lots when she just joined the company. Now as my feelings have developed I struggle to look at her, she thinks I'm rude or awkward because her behaviour has changed towards me.

All of this is the one reason why I believe I'm destroying myself right now. I've turned to dating sites, and have had unprotected sex with a string of women. I drink a little too much. Not many women on dating sites are down for anything other then a fling. I want to have a relationship or friendships.

Another reason why I feel I've gone off course lately is that my one close friend. Is veering off to the political right. Not an issue for most people but we are both politics students...and she's getting close to the far right. I've only had two friends, I depend on and I don't see them often. The thought I might lose her worries me immensely.

I'd love to increase my circle of friends but my shyness no social issues, just forever seem to get in the way. No matter how hard I try.

I'd like to go clubbing and to bars again. Just to have fun but I can't go alone.

Sorry if it's hard to read. I'm using the smallest keyboard ever.

Do you have staff email? Maybe you could just email her and ask her how she is? If she does have the mistaken impression that you're rude then maybe doing that would remove it. Seems like at some of the places I've worked, it was normal for a lot of people to just email each other out of friendliness.

Thanks for the response.

No, I don't. I should have pointed out we work in a supermarket. I have her on Facebook. We used to talk irregular then I didn't message her for 5 months. I asked her how she was doing last week and she saw it but didn't respond. Weird because we got in the lift the day before and we spoke even though I was a bumbling mess. I prefer to do things face to face rather then through messaging to be honest. Bad past experiences.

I've not had this feeling in ages. I can't even look at her because she makes me feel so shy like I was years ago. I feel like a teenager again.

I'll probably be leaving soon because I completed my degree. I'm actively looking for another job so.. But I'd still like to be able to get close to her. She's beautiful and she's nice to talk to. Of course she's popular with every guy.

Do you want to ask her out or just be friends with her? Maintaining a friendship with someone you have feelings for will be draining. If she's being cautious and distant because your feelings are seen through your behavior, whether you want relationship or only friendship, getting close as a friend seems a better option to me. Because she doesn't sound so ready to open up to you right now and asking her out right away seems so risky. On the other hand, since she's popular, there is the possibility of someone else asking her out before you do which makes such matters tricky. If you change your job before asking her out can't you just meet her in your former work place and ask her out?

Hopetracer said:

Do you want to ask her out or just be friends with her? Maintaining a friendship with someone you have feelings for will be draining. If she's being cautious and distant because your feelings are seen through your behavior, whether you want relationship or only friendship, getting close as a friend seems a better option to me. Because she doesn't sound so ready to open up to you right now and asking her out right away seems so risky. On the other hand, since she's popular, there is the possibility of someone else asking her out before you do which makes such matters tricky. If you change your job before asking her out can't you just meet her in your former work place and ask her out?

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To me it sounds more like she doesn't understand the reason behind his behaviour but I could be wrong. In my experience, women don't get that uncomfortable over a guy being awkward if the know it's down to him liking them (though that is very limited, anecdotal experience).

Matt4, I think you'll have more respect for yourself in the long run if you have a go at things rather than having to wonder what could have been. Maybe try and start small, see if you can muster up the aptitude for casual conversation and see if you can get things to grow from there.

In saying all this, I'm probably the worst person to ask for advice on this.

Just make conversation with her, and try to ask her out casually. Well, I know it's the workplace, so there might be SOME residual awkwardness to deal with, but other than that... what do you really have to lose? Especially since you mentioned that you might be leaving your job soon, you might miss your shot. Since you've had some success with hookups, you should at least know the basics of not coming off as a total creep. The only thing keeping you back is your own fear of rejection.

MentatsGhoul said:

Just make conversation with her, and try to ask her out casually. Well, I know it's the workplace, so there might be SOME residual awkwardness to deal with, but other than that... what do you really have to lose? Especially since you mentioned that you might be leaving your job soon, you might miss your shot. Since you've had some success with hookups, you should at least know the basics of not coming off as a total creep. The only thing keeping you back is your own fear of rejection.

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This summed up what I was trying to say more succinctly than I did.

Well shyness its the efects of negative sugestion and autosugestion from your childhood .The program shyness and social anxiety at *link removed* helped me a lot to understand the nature of shyness and how to gain self confidence in me an to love my person .All of this helped me to beat my shyness and anxiety also

MentatsGhoul said:

Just make conversation with her, and try to ask her out casually. Well, I know it's the workplace, so there might be SOME residual awkwardness to deal with, but other than that... what do you really have to lose? Especially since you mentioned that you might be leaving your job soon, you might miss your shot. Since you've had some success with hookups, you should at least know the basics of not coming off as a total creep. The only thing keeping you back is your own fear of rejection.

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Thank you all. I'm writing from an iPad so finding this a bit awkward then at the desktop excuse me if the quotes or punctuation is messed up.

Firstly, It's hard to make conversation with her because I put a load of value on her. I fancy her, this is why I know try so desperately hard to avoid these situations. I have nothing else to lose. I asked another girl out my workplace out about 5 years ago and got rejected. Glad I did though because she turned into something not too nice at all! She's so attractive it throughout everything off for me.. I know that's shallow. She looks like Eugenie Bouchard, trains for her football matches lots etc
I try not to think of leagues but if there was a league, I'd be pushing on the boundaries, ha.

Yes, I'm pretty certain other guys are talking about her. One has made a move and got her number. She wants a relationship I know that much.

I think, the reason why I had success in the past was that I didn't place so much value on the other person. Yea, I may have thought they were hot but never fancied them. I'm going to be so focused on not being a creep etc and a million other things that I'll probably look like one

To be honest, the age gap is another thing. She's 20! Seven years younger, after the experience with my ex who was 23. I'm not really big on dating anyone younger, maturity reasons, and I tend to like people my age or older. I'm 27.

I'll try some basic conversation when I see her. If she doesn't avoid me again.

Thanks for the advice all.