Italy has been on my bucket list for a long time. During my divorce, while I was busy paying my attorney almost every penny I made, my ex took our children on two, count them, TWO European vacations to Italy. I found myself home alone and so pissed off that I developed stress induced IBS. That’s code for the squirts.

So of course, once my divorce was final I decided to plan a trip to Italy. I bought the books, watched the videos, and devised a loose plan. Fly into Naples, rent a car and drive down the Amalfi coast in a tiny convertible with large sunglasses and a headscarf flying in the warm Italian breeze. Once there I would bask in sun soaked beaches, eat ripe sweet oranges on balconies covered in brightly painted tiles, overlooking the Mediterranean. In the evening, donning a white linen dress and leather sandals, to stroll through cobblestone streets toward restaurants offering death by pasta while saying “Ciao!” to tanned 5’2″ Italian men.

Being single can be a hard gig when it comes to travelling. Finding a good travel partner who is equal to the task of your vacationing style, financially equivalent and fun is a challenge. I invited a good friend to go along with me and she immediately got excited over the prospect. We started to daydream and then research on our girl night. Things were looking good.

“Hey, I found a really cool idea. You can book a room on a yacht on the Amalfi Coast and it will cruise around to the different spots. It’s a little more expensive but how amazing would that be?” She suggested.

“That does sound amazing. How much more expensive?” It did sound amazing, it was considerably more expensive. But then the changes started to come in greater quantities.

“Can I bring my husband and kids?”

No, this is supposed to be my vacation. That’s what I thought.

“I guess so, I do love your family.” Is what I actually said.

“Kids will still be in school at that time, can we go a few weeks later?”

That will be the peak season and everything will be more crowded and more expensive. “I can probably swing it since it’s only a few weeks.”

“How about a yacht trip to a different part of Italy, I hear Amalfi is crowded.”

It will be crowded because you changed the dates. “Well what do you have in mind? I guess Italy is Italy.”

“How would you feel about inviting another couple? My friend and her husband would love this.”

Now I get to be a fifth wheel instead of a third wheel? “I suppose the more the merrier.”

“Maybe the fall would be better than the spring.”

Amalfi is a summer destination I don’t want to go in the fall. “Maybe it would still be pleasant weather.”

“What do you think of a River Cruise in London instead?”

That’s not even close. “That’s on my bucket list too.”

Before I knew it my dream Italy vacation was completely hijacked. Now she wasn’t coming with me on my vacation, I had become a guest tagging along with her on her family vacation to London apparently. In the fall when it’s cold. The difference from my vacation and this one was about as far apart as Italy and London. I had people pleased into an entirely different nation.

When it came time to start booking, and here is the kicker, she backed out.

Backed out! Cancelled, flaked. She had some other things on her plate with her family that needed to take priority. She set a perfectly reasonable boundary and I was left holding a vacation I didn’t want. I was annoyed but the reality is I said yes, to everything. Why did I do that?

I’ll tell you why, because I’m laid back, easy going, flexible. These are the stories I’ve told myself for years but the reality is I’m a people pleasing push-over. Well, I used to be. It’s a work in progress. I wasn’t being laid back, I was abandoning my dream. I wasn’t being easy going, I was being a follower. I wasn’t being flexible, I was being dishonest.

Do you know I still have not been to Italy. I was so discouraged that I dropped the whole idea and shelved it for “To do someday.” That can be the price of people pleasing, your dreams get put on a shelf while someone else is out there living their best life.

She was not being selfish to express her desires or to prioritize her family. I would not have been selfish if I had said at the beginning, “I already have a plan. Let me know if you want to join.” But I did learn a lesson I’d been resisting for a long time. I’m not selfish for having my own desires, dreams, needs and preferences. I actually love it when someone else plans an entire vacation and I just tag along. But there are times when I want to do what I want to do and there is nothing wrong with that. It doesn’t make me difficult or, god forbid, bitchy. No one wants that, it’s like the worst possible curse for every cool girl ever. Setting boundaries that protect my dreams actually makes me more interesting, happier and a better friend.

We are still friends because she is an amazing person but she has taught me a lot about expressing my wants and holding my ground. We often talk about boundaries and she is always the first one to tell me, “It’s not selfish.”

Now about Italy, just writing this made me realize I need to take that dream off my shelf and dust it off. I’ve discovered that I don’t mind traveling alone, so … when I close this laptop, I’m going to go back to planning a trip to Italy. And if I invite someone I will say, “I have a plan, if you want to come, great.” Love ya, Ciao!

More on this, if it’s landing: if guilt is what’s been keeping you from saying the true thing, Feeling Guilty Is Not The Same As Being Guilty digs into that. And if you’re still figuring out where you fit after a big life change, Where Do You Belong? goes deeper.