Look for a bar where there's more than just drinking - pool, shuffleboard, trivia night, etc. There's always a group that's one person short. Find anyplace that you like - coffee shop, dog park, or whatever - and go at the same time each week. You'll begin to see regulars and then it's easier to start a conversation because they already feel familiar. Take along a book you like, read a few pages, and then set it on the table. A book looks more interesting than scrolling your phone and can be a good conversation starter. I went to a whiskey tasting recently and it was packed with men over 40!! Seriously, like 50 guys and 5 women! Liquor stores here do free wine tastings on certain nights- there's always a line and everyone's chatting while they wait- is this your first time, what are they sampling today, have you had it before, ...