Poker night has been my only attempt at socializing the past several years. While very simple to arrange and host, with my small circle of friends it has been difficult to get a crew together.
Ideally, I would like to play every other week with a rotating group of 15 or 20 guys who are comfortable taking swings of $40-$60. The problem is that poker similar to other activities quickly creates a pecking order where weaker players will de-select and strong players will not be able to find action. With a core group of equally talented individuals this is a non-issue as players just pass money back and forth in the absence of a house rake. Luck will over a long enough period of time even out.
This is the bane of casino poker. The house is pulling money off the table every hour and while short term swings can cover a 10% rake, long term this is a losing proposition.
I am hesitant to organize other activities like group bicycling rides or getting together for tennis because I am self conscience of my skill level. I would be embarrassed if I were to slow of weak compared to others. While this should not be the case it often is.
Golf is an activity where people of varied skill level can somewhat enjoy the game together. While a very weak player would slow the whole group down, this can be offset by playing a scramble or best ball style.