I have been sitting here for 20 minutes, what is taking so long? The restaurant had only opened minutes before I arrived and the lack of significant patrons in the restaurant confirmed I was in the first seating. My waitress looked nervous and I’d overheard her chatting with the shift manager about “some tips for managing your first fully booked lunch shift” so I had gathered that she was new.

But I had picked up the menu at least 5 times now, looked for a few minutes and after placing it back on the table, glanced around at the room. I was ready to order. Could I have waved her over as soon as I decided? Yes, but I was enjoying my book and wasn’t in a particular rush. Plus I didn’t want to get pushed off the table.

I was on my second day in London on another solo trip. I had already finished one book and logged over 15,000 steps each day traversing new neighborhoods. This meal was a much welcome respite in the middle of a jam packed day. But at this point, I had figured out what was going on.

She thought I was waiting for somebody.

I recognize that solo travel and solo dining isn’t the norm. And as I write this, I know that some of you probably are thinking, “Oh, that’s great that she likes traveling solo but I wouldn’t be comfortable with that.”

So I decided I needed to clarify something.

While solo travel can help you get comfortable being alone, its most powerful benefit is learning to be comfortable with being challenged.

And in this way, my philosophy toward solo travel and dating converge.

When you are traveling solo, you are practicing a behavior that surprises people. For that reason, you will come up against those who, intentionally or unintentionally, challenge your behavior. And that's a good thing.

When I realized that this waitress wasn’t ignoring me but rather trying not to bug me while I waited for a dining partner, I waved her over. Can I place an order please? Surprised, she looked back at me and said, “Oh, I thought you were waiting for someone!” Nope, just me!

Just me.

In this small moment, I had the opportunity to either own my decisions or apologize for them. You can’t hear the tone with which I responded “just me” but it makes all the difference. Excited. Apologetic. Proud. Ashamed. Disappointed. The way in which you say the “just me” is the revealing moment. We should be watching for those “just me” moments through every part of dating and relationships.

How we feel when we encounter someone with different views or expectations is most importantly an opportunity to check in with how we feel about ourselves.

I am a practiced solo traveler. Even before I started taking international trips solo, I was doing solo dinners in New York. Solo museum days. Solo walks with no earphones on. I’ve cultivated this skill over years - a combination of enjoying the company of my own thoughts or a book and reducing my anxiety over the opinions of others if I am seen alone in the world, on purpose. Even so, there are moments when I’m solo where the “just me” comes out disappointed. Other times it sounds fully at peace.

But I wouldn’t know if I didn’t take the trip. Go to the restaurant. Visit the museum. If we are never challenged, we never get the chance to evaluate and sometimes, decide to change.

When we are on dates, or seeing somebody new, there will always be moments where they react differently than we expect or they question something we take for granted. Our reaction to these moments, just like the “just me” statement can give us a clue how we feel about the topic.

Okay, now, people pleasers - listen up. This next part’s important.

If, like me, you naturally lean toward people pleasing behavior, your natural instinct is way more focused on collecting information about what makes the other person happy. This may feel very generous. You may think it makes it more likely the relationships succeeds but you'd be wrong. It clouds out your ability to listen to your own thoughts and feelings.

You notice your date bristles at the pop music in the bar at your first date and you log the info to not take him to the kitschy bar you and your friends loves that plays endless 90s nostalgia music. You’re not actively rejecting pop music, lying with “Oh yeah, it’s the worst” but what you’re doing is almost more insidious - you’re noting how to make tiny alterations to who you are with him in order to create a version of yourself you think is most likely to be accepted. And in doing so, you're filing away at the fine details of what make you interesting, compelling and attractive to the right guy (or girl) for you.

People pleasers are really good at overriding their own preferences in an attempt to make the other person comfortable. But in doing so, we are forgetting two key truths:

  1. You are allowed to have preferences different than your partner. Family. Friends.

  2. Sometimes those differences are actually a good thing. Sometimes people like us for the reasons that we disagree or are different than them.

What if he hates pop music and you love it. Couldn’t a relationship work between people of different music tastes?

She is a homebody and you love nights out with your buddies. Could a relationship work between people with different social schedules?

Spoiler: there’s no hard and fast answer to any of these questions.

But when you log an opinion or a point of disagreement in your people pleaser brain as “topic to avoid” or “behavior to fix,” you’re not allowing for the possibility that it’s actually not a problem.

Contrary to your natural belief, you can be fully yourself and be loved and accepted.

One of the most important muscles that solo travel helps you build is recognizing when your opinion or reaction to something differs from the person in front of you without automatically requiring a change or adjustment.

When you are on a solo trip, you cannot magically have another guest appear across the table from you. So even if you wanted to people please the heck out of that waitress, you can’t! No matter how much the waitress is or isn’t judging you for eating alone, you are eating alone. So instead, you have an opportunity to register your feelings about “just me” and just observe.

If we are going to find a relationship where we are able to be deeply, authentically ourselves, we will have to have conversations and interactions where our beliefs, opinions or behaviors are different than the person expects from us. And we have to be able to manage that difference without jumping immediately to bending over backwards to make ourselves more like them. And we have to recognize that us being different isn’t automatically a bad thing.

There’s one subtle distinction to make here. There is plenty of room in relationships for compromise. In fact, I doubt a single relationship works without it. But people pleasers often make accommodations without being asked. They also are more likely to adjust personality traits in addition to actions. “Oh yeah, I’m easy going!” when you’re really more comfortable with a complete plan. Demure when you’re really strong-willed.

Compromise exists in the space between two people with differing views. If you never acknowledge that you have a different preference or reaction, but make an adjustment, you’re people pleasing.

Own that solo meal. Your love of pop music. Your strong willed-ness. Your love of nights out. Can you find ways to challenge yourself to be exactly who you are and just notice when somebody expects something different of you without feeling like you need to change it?

If it’s really important, let them have a conversation with you about wanting to stay in more. You can even proactively bring up the conversation but as a compromise, having acknowledged first that you have a different desire.

Yes, I love Taylor Swift. I like nights out with friends. Just me.


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