Sitting in Starbuck's studying for Calc II when randomly an older man comes up and says something about Calculus. Although I'm kinda weirded out because he's a random old guy, we strike up a good 5-10 minute convo. I notice this cute 'older' woman (late 20s-early 30s range - I'm almost 20) in the corner of the store listening in on our conversation and smiling a little.

The guy leaves and I go back to studying for another half hour or so. Eventually I look up and the older woman and I make eye contact. I smiled, and that was when I decided DGAF about her age or what comes of this conversation - I'm gonna approach. I used the excuse of getting up to grab some napkins to walk by her, and at that moment I notice a guy walking his two german shepherd puppies outside. I use the dogs to open and we eventually get on the topic of Finance - she's trying to get some professional finance licenses. That's great, because I'm a finance major. Body language turns to face each other. There's the hook, BAM.

The conversation continues, turns deep, and she eventually asks me if I'm interested in employment in Finance. By the end of the conversation I've given her my info, she's given me her card, and I'm being invited to a company event where I'll get to meet her superiors and possibly land a paid summer internship.

TL;DR: I approached a woman, outcome independent, and now I possibly have a summer internship. If you're not approaching people, you're missing out on tons of opportunities. Don't let life pass you by.