Firstly I'd think seriously about mechanical_fish's advice - if you are still depressed get help, and this relationship you are about to enter into, whether as

Firstly I'd think seriously about mechanical_fish's advice - if you are still depressed get help, and this relationship you are about to enter into, whether as a friend or lover is not going to help, relationships have highs and lows, and people who are already feeling low can get influenced by that - so try and get on top of that problem first. Next problem you are asking about is should I try my luck or just be friends with this girl. I've never been in your position (not an introvert) but I have seen literally dozens of people in your position. Being friends with someone you secretly fancy does not work. She will get a boyfriend, you will get upset. She will stand you up as friends going to dinner, you will get upset etc etc etc. In my opinion you have to make a move, and if it works then great. If it doesn't then that doesn't necessarily ruin your chances of being friends. I've certainly seen people have lasting friendships after rejecting one party for a relationship - as long as both parties know the score. I have a very good friend who is in your exact situation - for the 10th time in about 10 years - every single "friendship" has ended in disaster because he has never manned up and told them how he feels. So that last part of your puzzle is how to ask her out. I'd imagine 99% of people on the planet struggle with asking someone out, especially someone they know. The best way is to man up and just ask her out (maybe have a drink first, but not 10). On your way out from the bar after your cycle trip ask her if she'd like to catch a movie sometime, or a meal, or one do one of your mutual interests. Be fairly direct to ensure there is no confusion over the reason. Hard to do I know, but it works the best, and despite all the teen movies you may have seen she is not going to run around telling everyone awful things. The worst she is likely to say is no, or no I have a boyfriend etc. And of course the best she is likely to say is yes :-) Good luck, it really isn't that difficult, most men and most women are generally keen on meeting a significant other and don't mind being asked out.