Hey guys, i'm hoping you can help me. I don't normally check this reddit out because I don't feel I belong here. I'll try to keep this as simple as possible.

Background: I'm 29(30 in 2 months) have been single since I turned 29(literally. my girl left me on my bday) and that relationship was 4 years long. Since I was with her, my social circle has diminished and most of my friends all found significant others and/or have kids. I need to start dating again. Dating sites aren't working out for me. I have huge self-esteem/confidence issues and find myself with fewer and fewer people to even just bullshit with on the phone...

Problem: One of the clients I work for has an intern that I like. She's not a 10 by any means, more like a 7.25. I speak to her very briefly when I help her with her IT issues and most of that pertains to work and what we're trying to accomplish. I've probably spent a good 7 - 10 minutes total getting to know her as our schedules are wildly different. My last days of working at this client are fast approaching and I feel if I don't act soon, I may never run in to her again.

The question: How do I get the balls to talk to her? How do I bridge the cap from being "the IT guy at work" to "the guy that stuffs her?" What are some tips or techniques that I can employ? I'm a fairly(VERY) negative person with a shitty outlook on the world. I'm not a good looking guy. I'm probably average in every respect. If this post doesn't belong here, let me know and i'll go elsewhere. Thanks.