If you’re reading this, one of two things are true:
1.) You are the glue that holds your friends together. You organize outings, arrange seats, and find the good restaurants next to the better ultra hip bar/arcade/barber shop/shooting range/artisanal foie gras stand.
2.) You think you are, but could be doing it a whole lot better. As a matter of fact, everyone could be doing it a whole lot better -- and if you identified with #1, take heed: just because it sounds hip doesn’t mean it’s actually a cool place to hang out. You have much to learn as well.
Eat the fees
Whether this means paying an online ticket vendor its usurous convenience fee, paying a deposit for use of a gym, park space or bar, laying out up-front cash for time on the golf or tennis courts or whatever other incidental costs might appear when planning a day or evening out. Waiting for every single person in your crew to pay their own way in is a sure way to be disappointed. Oh, and unless these fees amount to a sum that really puts a dent in your finances, don’t ever mention them again. Your friends will be more likely to go out for something you planned if they know you’re not the one who’s going to badger them over a Ticketmaster surcharge until intermission.
Learn the art of compromise
This is a prime example of making a small sacrifice to make the most people in the group happy. If you’re dying to try the new sushi place near you, but you know at least one of your friends will complain about how gross she thinks raw fish is all night, and another one of your friends will start to huff and puff every time friend #1 complains, avoid that eventuality altogether by choosing a more neutral food option for your group of friends. If you have a regular spot, don’t feel the need to break tradition for the sake of doing so -- sometimes we gravitate towards the same places for good reason.
If someone in your group has a new significant other they want to bring along, smile and say yes. Plan for an extra, pay their fees if there are any, and treat them like one of the guys. Is it ideal to have to put on your “meeting new people” face while you’re trying to hang out with your friends? Of course not. It sucks: Can you swear? How much can you drink? Can I tell this story in front of them? Will they murder your friend for their comic collection? But with any luck, you’ll only have to put on that face for a few minutes before you realize this person really could be part of the gang if you’d let them.
Don’t be a gym class hero
If you’re at a cooking class, don’t talk up your perfect tiramisu. If you’re mini golfing, don’t wear spikes or a golf glove and make everyone sign your winning scorecard. If you’re going to comic-con, don’t berate your friend who doesn’t know the Infinity Gauntlet from the Hand of Doom. If you’re bowling, don’t go all Walter from The Big Lebowski and threaten someone with physical violence. You get the idea.
Be flexible (even if it hurts inside)
Some of us are natural organizers. We color code, phone ahead, arrive early and pre-read the maps. We’ve got an itinerary in our heads when our friends show up, and sometimes it’s hard to let go of that. But it’s better if we do. Let your inner control freak go and let your friends wander off if you want. If, at the aquarium, they want to see the penguins first even though your plan takes you to the seals, take a deep breath. Everything will be fine, and everyone will see the penguins in their own time. We promise.
Practice your poker face
Not every outing you plan is going to be a rousing success, and that’s fine. What matters in these situations is how we react to planning a bust. If someone makes fun of your failed adventure, try to laugh right along with them, then try again next week. Just don’t get all defensive and alienate yourself -- no one wants to hang out with the person who’s going to judge them for not having a good time.
Don’t try to plan next week’s fun during this week’s fun
If your day is going perfectly as planned and everyone is having a good ole time, don’t spoil the moment by trying to get your crew to agree to next week’s outing. Even if it’s something that needs to be planned a week in advance, it can wait until everyone gets home. Just relax and enjoy the fact that you made the impossible happen -- you got people together in real life.