This should really be titled: How to talk/flirt/banter with work colleague over email or How to let a girl down gently without hurting her feelings. This is the dilemma I find myself in.

A little about me:

I am a mid-20s guy. Never had a girlfriend. Lost virginity to prostitute aged 21. Had sex one times since with random girl in club (she 'picked' me up). I finally got my first job ever a few months back. It is working in an office/cubicle environment. Had some rough times over the past few years. Life is starting to improve for me. Well, it was, at least. But I will get to that part. Anyhow, I feel like I am a good looking guy and I am well groomed and look after myself. I get a lot of heads turning in work and it was the same back at university. I do not walk around like the most unconfident person in the world. But deep down I feel like a loser, lowe self-esteem, low confidence, clueless with women.

The Situation:

Was in work today. Work friend says to me out of the blue that there is someone in the office interested in me. He did not say who. Right away I felt nerves I had not felt in years. Felt like I was about to turn red. He says he got an email. I say forward me the email. I reluctantly check my email. There is his email and one from another work friend. The one from friend #1 has a quote from the girl saying she thinks I am 'cute'. The one from friend #2 says girl x is interested in me and she is too shy to email and I should email her. I felt sick in the stomach.

I knew who the girl was. I had noticed her looking at me often and smiling. I will be honest. She is not my type. Too fake. But I would no doubt have sex with her, you know, a one night stand kind of thing. But that is as far it goes. I would not want a relationship: a) she's not my type b) she has a kid - would not even go down that road c) I want to be free. I have dreams to travel the world. Don't want to be tied down. Pus I have always be single and sort of used to it now.

Anyhow, back to the story. A few times as the day goes on, one of the guys brings this up and says I should email her and I should 'get in to her' and he will set this up. I feel sick with nerves and anxiety everytime he brings it up. I try to forget about it and get deep in to my work but it is impossible to concentrate. I feel like I need the toilet. I feel sick. I let out gas a lot. I eventually go the toilet for a number 2 but it is not long before I feel I need another one. I just want the day to end. The girl was facing my direction but there was something obstructing us so we could not see each other directly. I just sunk in my chair. I have to walk past her to go the toilet so I tried to avoid that.

Then I go in to my email for work reasons, and as I do, I receive an email from girl-in-question. She says half-jokingly that she was forced to email me by the guys. I reply saying thanks for earlier compliment. She aks what compliment. I say maybe the lads were winding me up and quote what she supposedly had said. She confirms it was a wind up and she had in fact said I was 'cute'. I say thanks. She says surely I must have noticed by the amount and way she stares at me. I half-pretended I did not notice. She says I must be oblivious. I say something like, people stare at people all the time, does not mean much. I take a long time in between answering the emails, where as she was replying immediately. I was just really nervous and felt sick. I was scared of writing the wrong thing. Scared of showing too much interest. Scared of hurting her feelings. Scared of saying something stupid.

My main problem is this. I do not want to give her false hopes. One of my biggest problems is I am too sensitive to other people's feelings. I do not want to make people feel bad or be responsible for making someone feel bad in some way or another. I also believe a lot in karma. And this has been a major problem with girls: what if they are after a relationship but I only want a one night stand, I do not want to make them feel bad / hurt their feelings. And this is one of the reasons I am scared to approach girls. And this is a problem I have with this girl, I think. As I have said earlier, I would give her one and that is that. But what if she is looking for a boyfriend, someone to be a step daddy for her child.

1) How would I approach this for the one night stand aspect? What would I say over email? How do I have playful banter over email? What should I say if I talk to her? What if we are walking towards each other? Is she expecting a boyfriend or is she is expecting a fuck? How would I know. I am not what you would call sexy. I do not have a hot body. I am skinny. I just have a nice face. Aren't I the sort of guy girls want to be their childs step-daddy?

2) How would I let her down gently? Not just blow her off like. Not just avoid the problem. I will have to see her in work every day remember. Plus I am sure other people no about it and do not want to be some talk of the office.

3) What the fuck would you do in this situation? What should I do, please?

I am in work tomorrow and I am lying here feeling like crap. So nervous and anxious. Like I just want the world to swallow me up. It is a long day tomorrow. Today this thing started near the end of the day. Tomorow I may have to deal with this the whole day. I am scared. Then what about the next day and so on.

I just know the guys are going to pesture me tomorrow, as guys do. They are the sort of guys were if a girl shows an IOI they would not hesitate. The could not understand why a guy would be nervus around a girl or say no to a girl. There the sort of people who will tell other people too and scared lots of people will no. I swear my life was getting good and now this thing has happened. I feel like getting a new job now. I am under pressure to improve my performance at work at the moment and this thing does not help mattets.

Please reply as soon as as I have to get to bed in the next 40 minutes or so as it is late here and as mentioned I have work tomorrow. I just need to go in to work tomorrow with some preparation, some advice. I am already thinking of taking what would be my first day off.