I'm a 25 year old male and a graphic designer at a pretty prolific printing company in my city. I consider myself not so much a people-person, in that I hate crowds, I hate being in large groups with people I don't know. I completely close down and just end up feeling depressed.

I am not too shy, but I do lack confidence when it comes to speaking my mind. I'm not one for drama or embellishing or divulging my innermost, personal pains and prides, but I am getting better at holding conversations with people, making them laugh and so on. I do work with and meet with strangers often for my work, so that's amazing practice that has paid off a great deal over the last 5 years of working for this company.

I am, however, getting a very late start in my life. I never went to high school. I was homeschooled, and so I missed out on a lot of interpersonal interactions that could have really bolstered my social fluidity. As such, I'm a 25 year old virgin who has never had a girlfriend. It doesn't bother me THAT much anymore, but I'm tired of it. I mean, I'm not ugly, I have style, a sense of humour and so on. My problem really is just that I lack the confidence to step up to a woman and express my interest in her from the outset.

I learned that the hard way recently by getting rejected and friendzoned so hard I have whiplash, by asking out a girl I've been close friends with for more than a year.

But tomorrow I am going to be presented with an opportunity to express my interest in a girl I've met only once (she's a client, and we had discourse only for about 10 minutes discussing the project, then she had to leave with her friend.) Tomorrow she has to come and collect what we made for her, and so I will have an opening to talk to her. I have her number already from asking her to fill out a contact sheet for our client database, so I can call her also.

I'm not asking for tips, but tips are very welcome. I'm mostly writing this so that I can come back to this post and report on the happenings. Wish me luck!