Do you sometimes struggle to find dating enjoyable? Is dating something that makes you nervous, tense, or anxious, when it seems like something that should be fun or exciting?

If you find that you can’t seem to relax and act naturally on dates, then stick around, because today, we’re going to be discussing a small shift in your mindset that will help you to radically improve your emotional response to dating!

While dating can often seem hip and glamorous from an outsider’s perspective, the reality can be very different from the dream.

When we’re stuck in the middle of a relationship that’s just not working out, we see our young friends and people on TV shows living it up, and we get jealous. Once we’re on the date, however, we realize that it’s usually draining and confusing.

Often, even when things are going well, we’ll find ourselves thinking that it’s just not as much fun as you thought it would be. Why is this?


When interacting with others, we’re constantly navigating the lines we can toe—or cross altogether—with others. The problem is that we seldom look after our own feelings and preferences as carefully.

What do I mean by this? Here’s an analogy: picture your boundaries as a fence surrounding your ideal backyard. What do you see in this yard? Let’s say you have a beautiful fountain, a flower bed, and some great patio furniture. Now, imagine that a neighbor you’ve never met walks into your yard: How do you feel about them entering?

Some people would be totally against anyone coming in unannounced, while others would think it was just fine as long as the other person is friendly—either way, it’s good to know which you are.

Now, imagine that this person steps through your flower bed, rinses his hands in your fountain, and puts his muddy feet up on your furniture cushions—how do you feel now?

When someone crosses a line with us—even a small one—we often feel like we have no right to let them know.

This is why dating can be such a drag.

Even something as small as changing the subject to avoid a topic of conversation you hate can feel like a difficult or rude thing to do. Instead, you sit there like a hostage, being held captive to this person’s diatribe about antique doll clothes (no offense, antique doll lovers!).

So, why do we think that simply making our preferences known is selfish and wrong? Because we’re too busy people-pleasing and being nice to tune into our own needs and emotions.

For people with this tendency, dating scenarios increase it tenfold. In fact, in dating situations, micro-boundaries can virtually vanish.

On your typical date, micro-boundaries involve noticing all the little things you like and don’t like from moment to moment: the conversation, the connection, the other person’s behavior, his ability to focus, the tone of her voice . . . everything.

So, let’s take something basic: the topic of conversation.

As mentioned above, most of the time, we’ll just sit there and let the other person steamroll the entire conversation. This, however, is not necessary. Whenever you feel as though you don’t like the way things are going, you can simply assert a micro-boundary.

But, how do we do that?! Simple: you just do it.

Is that person talking about something that bores you to tears? Kindly and gently change the subject: “I had no idea you did that, and it sounds like you really enjoy it—hey, actually, there’s something I wanted to ask you about. . . .”

It’s that simple.

If you feel like this sort of thing is way too far outside your comfort zone to jump in all at once, then a better place to start might be one of my programs, such as Confidence University. This particular program is the most comprehensive I’ve ever created, covering in-depth topics such as social mastery, dating, setting micro- and macro-boundaries, and starting conversations with ease (and that’s just the basics of what we cover).

In the meantime, you can begin to absorb these practices and slowly develop the confidence to put them into practice.

Generally speaking, what you need to understand is that it is NOT your job on dates to be a people pleaser.

When you’re on a date, the primary aim is to discover whether or not this person is someone you’ll potentially want to be spending a LOT of time with in the future.

If you want to change the subject, you need to do it. If you want to ask a question, you need to do it. if you want to let her know that a subject she’s going on and on about is touchy for you, you need to do it.

Now, you don’t need to do any of this in a negative or critical way—even commentary on that person’s demeanor can be broached in a gentle way. Say, for instance, the person is being super negative and judgmental about everything he or she says. If that bothers you, you can simple say, “Hey, I’m noticing that you’re being very critical of the people in your life—is everything ok? I’m not trying to judge you; I’m just sincerely curious about it.”

If you’re going to possibly date this person long-term, you need to know if this is everyday behavior, or if he/she is simply having a bad day.

Now, let’s say the date goes well, and you want to continue to date this person. Now, you have to consider additional micro-boundaries that may come into play.

Are you looking for a relationship? How serious would you like that relationship to be? Are you cool with him hanging out at your apartment every night? Are you ok with her leaving a few toiletries at your place?

These are serious boundaries that you first need to understand about yourself and then communicate very clearly once they come up. If we fail to do that, we run the risk of allowing the other person to set terms for the relationship that we’re not comfortable with—we may even find ourselves stuck in a one-sided relationship for years because we’re too “polite” to speak up.

Frankly, that’s insane.

If you want to create a healthy dating life—and, eventually, a healthy relationship—then you have to be willing to recognize what you want, communicate it clearly, and ask for it effectively.

The truth is that dating is as much about advocating your own needs as it is about discovering and respecting the needs of the other person.

If you can’t speak up for yourself, I can guarantee that no one else is going to. If you want to create honest interactions that will lead to the best possible outcome for everyone involved, then you need to be truthful and open about your needs. If that person is the right one for you, he or she will understand where you’re coming from, and you will ultimately find common ground and a deep connection much sooner.

As always, I’m thrilled to share this information with you so that you can go out into the world and make it work for you in your own life. What are some of your biggest boundaries? How can you express them clearly in a civilized manner? What are your major difficulties when it comes to establishing boundaries? If you need some additional help getting into this work, you can also check out my book, Not Nice, in which we dive deep into letting go of mindsets that don’t serve us and learning to become more honest.

Until we speak again, may you have the courage to be who you are and to know on a deep level that you’re awesome.