Josh - I am the new guy here and I somewhat look like your 2001 picture right now.
I must say that I am very impressed with your results and I think you do look very good. What I mean is fit and in nice shape.
I am 32 yrs old, I stand 5'8" tall and I weigh around the 230 mark. I used to lift weights, but marriage and three kids will put a damper on your workout routine.
I gained most of my weight when the wife became pregnant with child number one. She would not eat unless I ate with her..and being pregnent, she needed to eat and eat she did. Fortunately for her, she lost almost all of her gained weight shortly after she had the baby..unfortunately for me, I didn't.
I would be interested in hearing more about your work out routine for my added benefit. My diet has got to change and I have started hitting the gym again now.
I may not be able to add any info to your work out routine, but I think I may be able to give you some advice on the self confidence with the girl situation.
Before I go on here, I would like to say congratulations on your recent date. It sounds like you are happy, but you are young and I don't think you should be looking to entertain anything long term. What I mean by that is that you should not focus all of your efforts on just one girl at the moment. If things workout between the two of you, then that is fine - and only time will tell if that will work. Some might disagree with what I am saying, but that is just my personal opinion here.
Here is my advice: FLIRT FLIRT FLIRT
When I graduated high school, I had self confidence issues just like you do. I was fit and in the best shape of my life - then. Heck, I was breaking weight lifting records at college and loving every minute of life - with the exception of a relationship or oposite sex attraction.
Then one day, I decided that I just needed to be myself and then people would find me. I decided that if I was looking for love, I would never find it.
I have always been a fun person to be around. When I was out with the guys, I was always getting in to stuff and partying all the time. But if you threw a girl in the mix - whether i knew her, or was just admirning her from a distance, I shyed away.
One day I was checking out at the grocery store, and there was this somewhat attractive girl behind the counter. I decided it was time to put "OPERATION ME" in action.
I just kind of leaned down on the counter and asked her name (she wasn't wearing a name tag). She told me her name and then I told her that I thought she looked very nice today. Not really anything too outlandish, but it wasa start. We made a little small talk and I flirted a little more..paid her for my groceries and left.
Well, I got to the truck, took out the receipt so I could write it down in my check book and low-and-behold, she had somehow written her name and phone number on the receipt while I was talking with her (I didn't realize that she had done that) with a small note that said "Call me" and a little smiley face.
Not only that, but she had given me an employee discount on my groceries. Now that wasn't right for her to do, but I didn't complain. Please no bashing me for my morals on that one.
I called her and we even went out once or twice. But i found out that by me being myself, it worked. I tried this again and again and again. Sometimes I got weird looks and snobby noses shoved at me, but more so than not, I got a positive response. Whether it was just a little smile and a thank you to a blush and a phone number.
I started using my new found glory everywhere I went and still do. The wife knows that I am just harmlessly flirting and she doesn't mind. I no longer look for phone numbers or anything, I just be myself and I always get a positive result.
By just being nice and polite and being yourself, you will be surprised at what you can accomplish.
Sorry for such a long winded post and I hope I wasn't too far off the content.
Keep your chin up - you will be fine.