First, let me paint a picture for you.
(har har)
Close your eyes (come on, bear with me), visualize yourself in that moment; you're standing at a park table. It's a beautiful, sunny, slightly breezy, Spring weekend day and you're walking your dog (you have a dog now), but you otherwise have no plans this afternoon.
"Birds are chirping." - your imagination
You come across an acquaintance friend who lives in your building. She's about the same age as you and is the kind of girl you'd like to be friends with. Maybe she's with some of her friends and it looks like they're... painting?... and drinking wine... and eating crackers (sure, there's sharp cheddar somewhere; well, there was ...still plenty of wine). Her friend sitting to your right just patted the empty space to his left - as non-creepy men drinking wine on weekend afternoons and painting with friends at the local park, offering bench seats to new ones are oft to do.

Now listen to your head respond...
"Would you like to paint with us?"
What are those first words that come out of your mouth?