"Youthful days of naive optimism" you say? Yet, if a male complains about being lonely and single, he's told to "man up" or be "positive." Damned if you do, damned if you don't, so I'll just choose my way anyway.
Man i hardly can look you straight in the eyes when i talk to my friends, i always feel the eyes are so judging when they look at you for more than 3 secs. I find nearly impossible to win an eye contact with a stranger. I hope i gain confidence after no faping.
Look at them for a few secs, raise your eyebrows and look to the roof, then look at them back and smile with your lips shut.
Hold eye contact and smile. If you're feeling playful and the situation warrants it, throw in an "I know, right?" look or a double-eyebrow flash. Eye contact is great for building relationship, even between complete strangers. I'd only say it's awkward if you stare and do nothing with your face and body - that's creepy.
It's about not wasting your time and being over-eager. There's a middle ground to passivity and cold approach; be observant at all times, in the present, and when you see the slightest interest reciprocate... and only if you're interested [never approach for approaches sake unless you are doing it for an exercise to get over 'approach anxiety']. It's the difference between a natural and artificial approach.