Problems with the first approach: Is it a good training to go to strangers, say hi and give them a genuine (&casual) compliment, then go again?

[HannesK]

The first approach is hard. I wanna get better at that and prevent it from getting awkward. I thought it would be possible to start lower, and first get used to approach people and exchange 2 sentences. That person would also benefit for getting their day brightened with a random, but nice compliment.

Do you think that is a good approach to the problem or do you suggest something else?

[Effably]

Sounds good to me. Don't forget simple additions like "Have a good day," or alike. If anyone is unsure of your intentions that quickly shows it was limited to only the compliment.

And if you want a tiny bit more practice, tell them what you're doing! "Hey so, I was working a bit on my social anxiety and am trying to basically say Hi to people and something nice. Figured you would be easy because that is a seriously cool hat.". That sort of thing is non-intrusive and will probably escalate things to a small response too. Good luck!

[ShesRad80]

best place to do that would be like a grocery store, randomly say good morning or have a nice day to a store worker and go from there. over time you will get better with it and it will be less awkward in general and it will improve your social skills

[Nikki1989]

Yes, practice makes perfect. Socialize and socialize often.

[Middle_Sch_Whirl_Grl]

Yea it's easy 2 say something nice to someone and then just walk away leaving them happy.

[Anonymous]

Sure, just don't overdo it.

[In_Trance]

Sure