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Ask Leslie

Your Guide to Life's Dilemmas

When was the last time you had a new experience?

I’ve been thinking about this lately as I watch my two daughters grow up. I have the awesome privilege of watching them try new things all the time. They’re constantly discovering, experimenting, learning and, yes, occasionally failing big time. But they keep trying.

As adults, I think we get a little too comfortable with what we know. We have our routines, our restaurants, our friends, our opinions and our ways of doing things, making “life” a very convenient excuse for not trying something new.

But maybe life should be the reason we do.

My family and I recently visited old friends who had just bought a country home in Salisbury, Connecticut. They live in Manhattan, and their new place is their quiet escape: a charming house, a lake, mountains, a real general store in town and plenty of roads and sidewalks to explore on foot or by bike. It was a completely different pace from our everyday life, and I loved being reminded how refreshing it can be to step outside your usual routine.

It got me thinking that sometimes, getting out of our routine is simply about being willing to look at things a little differently.That’s what I found myself thinking about as I read this month’s questions. 

One reader is trying to figure out how to gracefully navigate being uninvited to a wedding and then, unexpectedly, invited again (wait. what?). Another is trying to figure out the rules of tipping, at a time when every screen seems to be prompting us to decide what percentage to give.

So, how do we navigate those moments when the “rules” aren’t quite so clear?

My answer? With a little confidence, a little generosity and, as required, a little humor.

I’ve been best friends with two women since middle school. We lost touch for a while after I moved away, but over the past 10 years, the three of us have become very close again. I know their families, have been to countless family celebrations, and have always considered them some of my closest friends.

One of their daughters recently got engaged, and I was invited to the engagement party and helped with the bridal shower. So, naturally, I assumed I would be invited to the wedding too.

Then, my friend told me that she felt terrible, but they had too many people and she couldn’t invite me to the wedding. I was completely caught off guard.

I was pretty hurt, especially because this is a large wedding and I know many of the people attending.

Then, unexpectedly, I was invited to the wedding.

Now I’m not sure how to feel. Of course I’m happy to be included, but I can’t pretend the whole situation didn’t sting. Do I just show up, celebrate my friend and let it go? Or is there something I should say to her about how the whole thing made me feel?

What’s the gracious way to handle essentially being uninvited… and then reinvited?

Dear Uninvited,

Wow. Just when you think you’ve heard it all.

This is certainly an unusual situation. Given that this was a large wedding, it’s hard to use the excuse that they were trying to keep the guest list intimate. And even if that were the case, it sounds like you two are close enough that you would have made the cut.

I have a feeling there’s more to this story than you know, and given how close you are, I think it’s perfectly fair to get an explanation.

If you feel comfortable, I’d go directly to your friend and simply ask her about it. It doesn’t have to be a heavy conversation, you can even approach it casually or with a little humor if that makes it easier to get your feelings out.

And whatever you do, don’t go through mutual friends. Things can get filtered, misinterpreted and distorted like a bad game of telephone.

And now that you’ve been reinvited, go to the wedding! Enjoy yourself, celebrate the happy couple and have a wonderful time. Don’t let this awkward situation overshadow what should be a beautiful day. You can address your feelings with your friend separately.

I’m sorry this happened to you. But go into the conversation giving your friend the benefit of the doubt. Take the high road. That will always be my advice.

How do I know when and how much to tip? It feels like every checkout screen is asking for a tip these days, and I’m always tempted to be generous because I’m afraid of being judged by the person behind the counter, the server, or the delivery driver. Am I overthinking it?

Dear Tip-Toer,

To tip or not to tip, and how much to tip? That is the question.

Tipping has become so ubiquitous that we’re now being asked to tip for everything, and those little screen prompts can make us all second-guess ourselves. 

For me, what’s appropriate comes down to two things: what you’re comfortable giving and the level of service you received.

Personally, I have high expectations when it comes to hospitality, and I tip accordingly. Great service deserves to be recognized, while poor service or an attitude doesn’t automatically warrant 20 percent just because the screen suggests it.

Here’s my general rule of thumb. Feel free to borrow it or create your own formula:

Dining out: 20 percent is my standard for a good experience, with more for truly exceptional service.

Delivery: Depending on the size, distance and difficulty of the delivery, I generally tip somewhere between $10 and $30. With a tip topper if they come in, unbox and take away the cardboard. 

Hotel staff: I always travel prepared with $20s, $10s, $5s and $1s and tip throughout my stay as different staff members provide service. A little cash in the right hands can go a long way.

And when that tip screen pops up at the coffee shop? Don’t let it bully you. You are allowed to hit “custom tip” and decide what feels appropriate based on the service you actually received. A tip is meant to be a gesture of appreciation, and the scale is sliding. 

Want to submit a question to Ask Leslie? DM Leslie directly on Instagram (and follow along!): ask_leslie_official. All submissions are confidential and anonymous.

“Take the high road. That will always be my advice.”