Dear Alice,

I am a New Yorker who is in college at the moment. Several of my friends from school are living and working in the city this summer, and I love having them around. Whenever I make plans with them, though, I feel a great pressure to make sure they have a good time. As the person who knows New York best (the subway, good restaurants, etc.), I feel like it is my responsibility to make plans and decisions when we go out, and I feel inordinately guilty or embarrassed if the plans ever go awry (e.g., if I mistake the address of a bar, if a restaurant turns out to be unexpectedly expensive, or even if the local subway line unexpectedly switches to the express — things that are often totally out of my control). I know this is silly; my friends can clearly take care of themselves, and I know they don't depend on me for fun. But the pressure that I create for myself is detracting from my own enjoyment. How can I stop holding myself to these absurd expectations and just enjoy myself?

— New York Native

Dear New York Native,

Any New Yorker or visitor to New York will tell you that there's a whole lot to do in New York. The challenge is to know when and where to find it! Often, this takes some inside know-how. Such scoop can be sourced from natives, like yourself, chic guides, magazines, websites and random word of mouth.

In this case, you're the native, and you have opportunities to introduce New York newbies to your wonderful city. Sounds like you've become the go-to person for the insider scoop. While this is flattering, it can be a big responsibility. Eek! It sounds like part of you enjoys being the organizer extraordinaire, yet when things go wrong, you feel anxious and responsible.

There are probably many solutions to this dilemma, but one might be particularly helpful. How would you feel about sharing the fun and anxiety of planning activities with your friends? Yeah, you are the native New Yorker, but your friends are living in the city too. Chances are they might be interested in learning how to navigate the Big Apple as well as you do. New Yorkers know this coveted wisdom does not come easy. As you wrote, New York can be unpredictable, even for the best planners! Subway lines change, restaurants and bars close, etc. It's virtually impossible to plan for every possible snafu! Maybe, you could think of yourself as their city tutor. In this way, it's unavoidable to run into unexpected diversions and last-minute changes of plans because that's how New York operates. Perhaps part of helping them learn New York can be modeling positive ways to deal with the unexpected in a city this size.

While you may enjoy being the outing organizer, this makes you feel responsible for everyone's good, or bad, time. That's a heck of a lot of pressure to put on yourself! Sharing the planning with your friends will serve at least two purposes: 1) you'll surely feel less responsible for their enjoyment, and 2) your friends will get a little taste and appreciation for planning fun stuff to do in New York. They'll also learn how important it is to think on their feet when unplanned stuff comes up. Who knows, maybe you'll all start to find new and exciting elements of the city that you never saw before! Time Out New York and are among the many websites you can check out for upcoming events in New York City. Share these with your friends so you can plan your next adventure together!

Hopefully, taking some of the pressure off yourself will allow you to enjoy things more when you are out with your friends. It's likely that your friends will notice and vibe off of your lightheartedness. Surely, that'll support everyone's good time.

Have fun!


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