b1crunch - you should know that there are many other 39-year olds just like you out there.
It is true, making friends as a male in your late 30's can be tough. Everyone seems to either have established social circles, or reaching out proactively to new friends often seems like a business proposition. People also at this age are far more likely to focus on the foibles and mannerisms that 'bug' them or they wouldn't appreciate because they've become seasoned to social interaction and what kind of work that entails. Sometimes you feel like you'd rather not bother.
On that note, I would recommend do something that allows you (and everyone else in the room) to focus on a shared activity that doesn't draw attention to the initial icebreaking. You jump right into a team-based activity that makes you need to think quick on your feet. Then organically you'll find like-minded voices that - at the end of it all if you enjoy the activity - will want to discuss and reminisce over beers and laughter.
Things like Tough Mudder, Night-time jogging groups, festivals that require team work (like canoe sledding at Canoe Volant in Edmonton), gaming nights online (with local players) or trivia nights help with that.
I don't like when people say "meet my friends over drinks". It's too direct. Need to achieve something together for the ice to be broken.
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