Today was a sunny day and I decided to try and get out and do some approaches.

Pre-Game:

I started out by getting some coffee, and my plan was to maybe talk to whoever was working there to get me warmed up a bit. I order my drink, and the barista says to me "Do you put anything in your hair?" I said "No its just natural". She says "It looks good!" I say thanks (yes, I know its just her job to be nice), and try and make some small talk off that, saying, yeah I'm thinking of getting a cut soon, do you know any good places in the area..."

This small interaction had me feeling a little energized, and the compliment feeling good about myself so I go outside"

First approach

I noticed a girl walking beside me with her pashmina scarf wrapped around her face, making her look like a Bedouin nomad. I say to her "I like how you've used your scarf as a mask!" She said "Thanks! Gotta improvise". I respond, "looks cool! makes you look like a desert wanderer" She laughs again, but then for some reason I find myself just looking ahead and walking away. In retrospect I should have taken that moment to introduce myself and start escalating the conversation towards something more flirtatious/direct.

Second approach

I'm at a little vintage store looking at postcards, a girl is doing the same next to me. I see a card where the guy on it looks kinda like Alex Jones. I show the card to her and ask "Is it just me, or does this kinda look like Alex Jones", and she laughed and said "kinda, but i doubt they'd have him at a store like this". We trade back another few quips about the store then I just put my head back down and get to shopping. Another escalation opportunity lost.

Conclusion

I'm glad I used some wit and situational awareness to get an interaction opened, but I didn't have the guts to keep the conversation going to the point of getting a number, or to something where my interactions were more flirtatious. I'm half writing this as a reflection but also could use some advice on how to take an indirect opener and make the interaction keep flowing to some better places.