You have quite a bit to work with. Your confidence seems to have taken a beating. What you project is key. Relaxed, smiling, and confident are hugely attractive. I definitely agree with growing out the hair. Talk to a stylist about how to soften your look. As far as facial hair goes, that is up to what makes you feel comfortable and confident. If you just don't know, talk to the stylist. You will want a salon that has a lot of good reviews. You are looking for someone with professional experience who isn't afraid to tell you what they think.

I agree with most of the advice. Definitely the fade cut. Right now your hair says harsh. With fashion, go to a store that has clothes in it you like and ask the store clerk if he or she can help you pick out clothes. I knew a guy who did that and he always stood out compared to the other fellas. Regarding the advice about no jeans. Yes, still wear jeans. Just be aware that being well dressed is a huge confidence boost and women definitely notice when a man is dressed a cut above. Have a couple pair of slacks and a few shirts and/or sweaters so you can dress appropriately if you take a girl to a nice venue. For jeans, make sure they fit well and for cryin' out loud, none of that baggy boxer ass-crack stuff. I am sure there are some women out there who find it attractive. Most of the ladies I know think it screams douche bag and won't even look at a guy who's wearing that.