When a bunch of us relocated to the Valley, we would do annual FriendsGiving and FriendsMas. As everyone has gotten older and busier, more stressed out or departed, that's kind of gone by the wayside.
Later on when I had my startup, my cofounder and our manager-of-everything would find a place for all of the orphans who were like we had been - without anything to do for the holidays because they, too, had recently moved away from their social circle and family. Everyone wins.
So I say: bid the awkwardness and putting yourself out there. I look back at that era fondly and yes, sometimes it was awkward, but mostly it was not. It was always worth it.
(Ironically, this year all of our plans fell apart, so my wife and I are on our own.)
If I wanted to do something like this, how would I find the orphans? I honestly don't know any grown-up orphans myself. There's definitely a matchmaking problem for finding certain people. Would I put up an ad on the Internet or in the streets saying, "Hey guys, holiday celebration happening, wanna invite all the orphans out there!" Or? Genuinely curious.
sorry for the lack of clarity; "orphans" here was our way of referring to employees who had moved across the country and had neither family [sometimes not in the US at all] nor social networks due to having moved cross-country to join us.
I support this, but offer a word of caution: When we did a Friendsgiving, word got out and friends invited friends and we ended up hosting about 100 people. It was chaotic fun, but also a big lesson. ;)
Later on when I had my startup, my cofounder and our manager-of-everything would find a place for all of the orphans who were like we had been - without anything to do for the holidays because they, too, had recently moved away from their social circle and family. Everyone wins.
So I say: bid the awkwardness and putting yourself out there. I look back at that era fondly and yes, sometimes it was awkward, but mostly it was not. It was always worth it.
(Ironically, this year all of our plans fell apart, so my wife and I are on our own.)