I wouldn't consider myself socially adept. At least if there's any adeptness at all, it's certainly not genetic or any natural skill, but from years of deliberate practice.

> both sides of the equation be uncomfortable.

Why should you feel uncomfortable? Unless you have malintentions, which doesn't seem to be the case, there's no reason to feel uncomfortable. You're simply expressing yourself, spreading positivity, and giving the stranger the opportunity to connect with you.

I'm a digital nomad who generally travels solo to countries, so I have no choice if I want to meet people since everyone is initially a stranger. A couple weeks ago when I entered the locker room of a gym a man saw that I was looking for something, and told me "the bathroom's that way". After returning I said "thanks" and went to my locker. The interaction could've easily ended there, and my old self would've left it at that, but then I decided to ask him where he's from. Turned out to be a really friendly guy. A couple days later I invited him out to watch a game with some of my friends, we partied till 5am or so and had a great time, and spoke about potentially traveling together to some nearby countries.

As a single man (who hates online dating), when I see a particularly pretty girl my type I'd like to meet who seems approachable, I approach. Sure most interactions won't amount to anything - maybe she has a boyfriend/husband, maybe she's not interested, maybe she's not in the mood, etc. That's fine. And by the way, maybe I won't even be interested anymore after talking to her because attraction is way more than just physical. It's a two way street. (and don't buy into this crap that politely approaching someone is "street harrassment". One of my best friends met his wife on a subway train). No need to come up with some elaborate pickup lines or whatever, just be direct and upfront with your intentions, and then say whatever's on your mind. If they don't want to talk to you, that's their right - you have no entitlement to the attention of some random stranger, so don't take it personally.

In any case, it's not rocket science, and there's no need to overcomplicate it. You don't have to try to fit some certain mold. Just be authentic and genuine, and most people will appreciate you for it (so long as you're not being like an a*hole or something obviously). One of my friends who is the best at this is one of the quirkiest guys I know with interests and humor that many might consider esoteric, but he's successful because he's genuine and confident in his own skin.

It's probably going to feel awkward at first. Just take it all in, and focus on the process. Every step out of the comfort zone is a win. The "outcome" itself is out of your control and subject to extreme randomness so don't focus too much on that. The more you do, the more confident you'll be and the easier it'll get, until the point where it's no longer a "thing" in your brain, just like you probably don't get nervous talking to your parents/siblings.

> Where do you hangout that you can just casually approach and start chatting up people?

Anywhere is fair game - parks, cafes, gym, street, whatever. Just be respectful.