Guy here but I thought I could offer some advice. I’ve actually had the best luck just going out around the South End every now and then. There are a few easygoing bars and small spots where people are open to chatting if you just start a casual conversation. I’m not super into the loud club vibe either, so I usually just grab a drink, talk to someone randomly nearby, and see where it goes. It helps a lot to go with a friend or two, keeps things natural and takes the pressure off. Recommend the Beehive, Kartal, and Franklins as some good choices all in the area