A
male
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*immy2
writes:I am a 38 year old guy with not much experience of sexual relationships but a lot of experience when it comes to missed opportunities. 5 years ago I met a young woman who I really hit it off with. I worked with her but every time it came to asking her out on a date ( and she gave me plenty of chances), I clammed up and couldn't say anything. Missing out on being with a woman who I felt more strongly about than anyone I'd ever had this problem with when she ended up with another guy threw me into the most terrible depression and hurt I've ever felt in my life. I needed counselling for it and it took almost a year to get over the way I felt about her. Not to be outdone and determined to sort out my shyness, I jumped into a relationship with someone I met online. We were together 4 months but because of problems we both had, it ended (possibly for my part that I was still in love with the woman I'd missed out on). After a couple more months of depression, I felt ok and vowed that if I ever met anyone who I felt like this about again, I wouldn't hesitate to ask her out on a date. 4 years on from this and I'm now in a new job and it's happening again. A young very pretty woman started working there at the end of last year who I somewhat took a fancy to and started speaking to on a friendly basis but I never seriously believed she would ever be interested in me (I'd estimate there could be 10 or so years between us). That was until last week when the two of us were in the locker rooms leaving after an evening (we both share one evening a week, I do 4, she does 1) and she said something that took my breath away. She said how she felt bad knowing that I have to work on my section alone when she works with colleagues and that she really wanted to come in on her evenings off to sit with me and stop me from being lonely. I was so stunned all I could manage was a feeble 'aaahh'. What I really wanted to say and do on reflection was hug her passionately and tell how much of a pleasure she is to work with and that while I'd never countenance her coming into work when she didn't have to, if she wanted to meet up after work sometime when we were both free, then I'd love to take her out somewhere. She even said some time ago what pub she likes drinking in and to come down one day to see her since we both live quite near to each other (but I just took that as friendly) and although I have often passed that pub with the intention of going in, for some strange reason the place is hardly ever open. Ever since she said about coming in to be with me, my feelings for her have become so strong that I can't take my mind off of her but because we work in a very busy place (which also has taboos about staff becoming involved since it's the education sector), I seldom get the chance to speak to her and when I do I'm having to look over my shoulder. Secondly, word has gotten out that someone else likes her but she doesn't like him in that way although they were supposed to have gone out but I don't know if they ever did. Also, although I'm not as shy as I used to be, I still find it difficult to pop the question because (and this has always been my biggest problem) I'm terrified that if the answer is no, it will spoil what we have struck up, (which is something I treasure) and that will make her feel uncomfortable around me because she will know how i feel about her. My question is, how can i end this painful and perpetual cycle and finally get together with someone (preferably her) who I can fall in love with because i don't want to go through that terrible hurt of watching the woman I love go off with another guy ever again?
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male
reader, jimmy2 +, writes (2 April 2010):
jimmy2 is verified as being by the original poster of the question Thanks for the latest post. Just in response to that, we did nothing but communicate and I'd hope that due to the raport we struck up she must have realised I really liked her. I'd love nothing more than to have had a longer chat with her but circumstances of work (i.e we work in different sections), means that we get breaks at different times and can only talk when for instance I go off on a break and she's working on her desk alone and we manage to steal a few minutes of speaking together which puts the guy who i suspect she's dating at a distinct advantage because he works with her all of the time as they are on the same section and has spent more time with her both alone and on breaks as when he started, he was allocated to her to show him the ropes of the job. If I'd been able to have half that time with her, nothing would have stopped me from popping that question but I don't believe it's right to ask someone out within the first few days of speaking to them (like he reportedly did) as I would have thought that most girls would then assume that a guy only wants one thing from them. I wanted so much more than just that with her, but now it looks like it probably won't happen.
A
female
reader, anonymous, writes (1 April 2010): You may not realize this (but) when you don't try and ask the person out or communicate more - it's makes the other person feel rejected and almost like they've done something wrong. You owe it to yourself to try and get to know the other person better. That's what dating is for. You just want to get to know her better. If it does not work out. That's okay, too. But, at least you know and you never have to wonder, woulda, coulda, shoulda. And, you can move on if you have to. Carol
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A
female
reader, anonymous, writes (1 April 2010): You may not realize this (but) when you don't try and ask the person out or communicate more - it's makes the other person feel rejected and almost like they've done something wrong. You owe it to yourself to try and get to know the other person better. That's what dating is for. You just want to get to know her better. If it does not work out. That's okay, too. But, at least you know and you never have to wonder, woulda, coulda, shoulda. And, you can move on if you have to. Carol
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A
male
reader, jimmy2 +, writes (1 April 2010):
jimmy2 is verified as being by the original poster of the questionThanks guys,
Your advice has really helped to put things into perspective.
As for the suggestion about asking her what times the pub opens - I did mention that I went past and it wasn't open and all she said was 'how strange' but this was when we first spoke of this and I did smile and say 'that would be kind of nice'. The sugestion of sending her an e-mail is good but the e-mails are monitored and besides I'd rather speak to her face to face. I have to say I'm not what one would call a 40 year old virgin because I've had some experience during my last relationship 4 years ago, so it's not all doom & gloom on my part. The other thing which somewhat confuses me is that I have asked her (as for the suggestion above) if she wants anything from the canteen when I go on a break and she is in the area but every time she has said 'no thanks but that's really kind of you'.
I have not long finished work (we finish early as it's the easter break). I Had quite a long chat to her today (on a friendly basis) as I'm on holiday next week and I was chatting to her about what I might do on my time off and again asking her is she wanted something from the canteen and she again said no thanks, but still I couldn't say to her that maybe we should meet up and in a way I'm glad I didn't because when we left, her and the guy who was rumoured to have liked her left in a somewhat together kind of way (not holding hands or anything but quite obviously holding back so that they could leave together) right behind me when I left. I stopped and waited to cross a road because of terrible traffic and glanced back to see that they were waiting together for a lift which she normally gets. I am pretty sure this is not a recent development (at least not since she said what she said to me) but why say what she said to me last week if there wasn't something there between us? Does she pity me is that it? I still cherish her friendship & will always do so for as long as i know her but I'm feeling pretty hurt and upset at the moment because I've lost yet another chance to be happy in life. I'm really glad I've now got a week off because I think I'd break down if I had to go in next week & it would affect my work. Since it's the best job and the first proper career I've ever had, that would be something of a folly, especially since we are in the middle of a global recession!
So, what to do now? Try to forget & move on is the only realistic option I've got. There are several things I need to sort out in respect of my life (not least giving up smoking and keeping fit) so next week is going to be the start of that. Not the blissfully peaceful week off I'd hoped for but it will give me the time and the space to look at all options open to me and to start ticking them off of the list. Thanks for your advice guys - you have REALLY helped me to understand a few things. I just hope it won't take too long to sort out my feelings. XX
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A
female
reader, dearkelja  +, writes (1 April 2010):
 I think because you are dealing with shyness here and are further concerned about losing the friendship that you work on strengthening the friendship.
This will do two things, make you feel comfortable with her and allow you to get to know her in a non-threatening way. If you sincerely enjoy her friendship then cherish it. You also mentioned the work thing maybe an issue.
What I would do is say, "hey that pub you mentioned, I went by there the other day and they weren't open. I wanted to check it out. What are their hours?" Then when she says 9-12 or whatever you can suggest the two of you go there during that time and have a drink. Don't go right into a relationship, cultivate the frienship and move things on at a pace that is comfortable for both of you. If things move towards a relationship you both will feel comfortable. It's not like you're missing out and also, you can find out this way if she's seeing someone else or if she is indeed interested in you.
I agree with the other poster. You do seem like a great catch.
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A
female
reader, mystiquek +, writes (1 April 2010):
 Sweetie, take the other aunts advice. I know it won't be easy, but you have GOT to be brave and make the move. The girl has already made it clear that she likes you..don't let the opportunity get away! I think she was just waiting for you to make a move and was to shy to be any more forward. So she's leaving it up to you. Come on..you can do it! Find a chance to talk to her again, just make it casual like "Would you like to go get a coffee/coke ect.." It doesn't haven't to be any fantastic line..if she likes you..she'll say yes! And it sure sounds like she's say yes. Like the other aunts have said..ok..she might say no..but then again..she might say YES! (And I think she will). How will you ever know if you don't ask?? Please don't waste time wondering..be brave! YOU CAN DO IT! GOOD LUCK!
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A
female
reader, trishine +, writes (1 April 2010):
Honestly, you sound like a really nice guy who has had far too many missed opportunities due to shyness. You need to use the next opportunity you have with her to ask about the local pub and see if you can arrange to meet for drinks. She's already invited you to stop by so it shouldn't cause you too much anxiety to follow through on that. Don't become the 40 year old virgin who ends up alone and making up fantasies in his head about what could have happened if only he was able to get over his shyness. Good luck!
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A
female
reader, celtic_tiger +, writes (1 April 2010):
 Be Brave!
Tell her you like her, and enjoy spending time with her. If you find it difficult face to face, send her an email, ask her out that way. Just do something!!!!!!!!
I speak from experience here, having always missed the boat, train, car or any other form of transport when it comes to talking to the guy I like. It took me over 10 years to tell him how I felt. 10 years!!! Because we were both as shy as each other, and the times he did approach me, I literally clammed up and ran away to hide.
This is the turning point for you, and you are just going to have to grit your teeth and get on with it. She may turn round and say no, but she could also say yes! I would say the odds are much more to the yes answer, as she WANTS to spend time with you! How many people go into work when they dont have to, just to keep someone company?
Take the bull by the horns and talk to her!
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