Start at work if you aren't remote "Hey I'm mesaframe over in department, what department are you in?" in the break room or hall (NEVER the bathroom if you are male, NEVER, please watch Male Restroom Etiquette to learn the ramifications of talking in the bathroom https://www.youtube.com/watch?v=IzO1mCAVyMw )

Or if you stop for coffee some place regularly, eat some place regularly, etc ask someone that serves you regularly how their day is. For years I used White Castle for my socialization. I'd go in every Saturday and Sunday morning and order the same thing and would chat to the employees once I'd established myself as a regular. Similarly some friends and I had a Denny's waitress that we eventually followed to another location and then even to another restaurant chain as we were there so much at night that we became friends with her.

It was super easy to for me to become friendly with a specific individual when I would see them over and over with small exposure doses.

I've talked to strangers about Boolean algebra, the weather, how long the bus is taking, the slogan on the bag they're carrying and how it relates to their calling in life, and so on. I dated a girl for about a year that I met on the train and started a conversation by joking with her about filler phrases she had used in a cellphone conversation. And of course evangelists are always willing to talk about theology.

I think most people are eager to be heard, eager to talk about their experiences and feelings (even trivial ones like being impatient for the bus to arrive), and lonely. But most people are preoccupied and in a hurry much of the time. You have to be paying attention at a moment when they are willing, and then be able to give them what they want.

It’s a skill and like any other skill it becomes less anxiety inducing the better you get at it. You could start with complete strangers at (say) a coffee shop, so that if you get embarrassed well it doesn’t matter, you’ll never see them again (this is how I improved). Also, learning how to be rejected and bail out is part of the skill. I still get into awkward situations sometimes, but it’s happened enough that I can cut the conversation off and the embarrassment doesn’t bother me all that much

Remember that one time that one random person struck up a conversation with you and it was awkward and you never saw each other again?

Me neither. People generally don’t remember these things.

Strike up a conversation and it doesn’t go well? It may feel like the world is falling apart at that moment, but you can rest assured it will be forgotten, and sooner rather than later. And you may get a sense of accomplishment just from going through the motions and doing it.

Strike up a conversation and maybe make a new friend? Awesome :)

I also have anxiety. The way you deal with it is to talk with strangers. Start by expressing yourself more with the people you are already comfortable with. Something you might normally not share. Then start with chit chat with people who are less familiar. You will be chatting comfortably with people you don't know in no time. Isolating yourself is the wrong way and will lead you to dark places. I know. I'm better. It's scary, uncomfortable and totally worth it.

Start living life head first. I hate speaking too, but I put myself out there and make myself do it, because you really have nothing to loose. Life is sporadic and impermenant. You try and strike up a conversation with a stranger, fail, move on, the next day you've both forgotten eachother's face, the next week you've both forgotten about the event entirely. Most conversations don't matter at all.

Start simple - ask people on the street what time it is. It’s a simple opener that should help you with your anxiety, and you’ll see nothing bad happens.

"Here, pick a card. Any Card. Don't let me see it."