My go to before I was a bit more comfortable was to make drink suggestions, or talk about why I liked the drink they were getting.

Ex: “grande white mocha? Nice choice, have you ever tried it with (insert additional flavor here)?”

That way it doesn’t have to feel so personal, but it’s extra connection. AND if you have a manager or SSV who is into upselling, they eat it up.

My best advice is to give small compliments or ask a silly question. At my store we have a "question of the day" type of thing. "What's your favorite Disney movie" "if you could travel anywhere in the world, where would you go".

I'm VERY reserved when it comes to customer connections, I've gotten better over the years, however my voice is just naturally soft so I'm very "quiet". So whenever I talk to customers no one but the customer notices me talking to them, it's such a hassle whenever I hear my SM or other SSs tell me "you need to talk more" when even if I try to speak louder to all the guests and regulars they don't like talking to me cause they don't recognize me as a human but as some coffee robot. Just the other day I got written up because I didn't say "thank you" to customers after handing out drinks.

I had a fellow barista who complimented them. Just a simple "hey I like your hair," "cool shirt" or "that't such a pretty necklace" would work for our drive through.

When I am on hot bar or making a drink near a customer, I always ask if they have any plans for today/for the weekend. That usually stirs up a conversation and “connection”. Usually, if they say nothing much, I respond with sometimes those are the best weekends - a chill weekend with a movie or two.

I hope this helps - and if you are already smiling and saying hello, you are making a connection :)