Wright Foundation | October 1, 2019

What to Do When You’re
Sick of Dating

Are you sick of dating? It’s time to change your perspective on dating, take the pressure off, and enjoy the dating scene more.


A man kisses a woman's hand in a coffee shop: are you sick of dating and ready for a new perspective?

I’m sick of dating!

There are no good men out there!

Women are full of drama!

I don’t meet anyone I click with. I can’t find the ONE!

If these complaints sound like you, it’s time to rethink your mindset on dating. Here’s how to start having fun on dates, instead of dreading them.

It’s Not Your Date…It’s You

We’ve all been sold the Hollywood idea of dating. We see romantic comedies where two people find their soulmate. Typically, through a series of mishaps (some ridiculously outlandish), the stars align, and these two lonely people find each other and feel fulfilled.

This very idea of this type of fairytale romance sets us up for failure. In fact, it’s a bunch of bull.

True romance comes from sharing intimacy with another person. It comes from opening up. It doesn’t come from sex, either. It comes from engagement.

Now, I know it may not sound as exciting at first. We want someone who lights our fire and gets us excited. We want someone who stirs up our feelings and piques our interest. But most people are multi-layered individuals. If we’re really working on getting to the heart of who they are, to connect, and to see and listen to them, we will discover everyone is interesting.

That doesn’t mean you’ll experience a romantic connection with every person you date, but you can enjoy a human connection.

The idea of finding “the one” has sent us down a difficult and misleading path. We’re searching for someone who completes us, who fulfills us and makes us feel whole. But you are the only one who can truly make yourself feel whole. It’s not your date’s responsibility, nor is it even in their capacity. You may feel turned on and intrigued, but don’t mistake those feelings for fulfillment.

So, what’s a single person to do? How do you start going on better dates?

If you think dating sucks, you need to take a step back and assess. Has it occurred to you that when you’re on a date, you have all kinds of thoughts you aren’t saying? There are plenty of ideas and judgments going through your head. Maybe he’s a loud chewer. Perhaps you didn’t like what she said. Maybe you aren’t sure what to order because you want to make a good impression. Perhaps you’re wondering if this person has potential as a partner in the long term.

It’s your cowardice keeping you from saying what you really want. It’s fear holding you back from expressing your wants and true yearnings to your date.

Opening Up: What if You Told the Truth on Your Dates

What if you radically told the truth on your next date?

After all, it’s not the other person’s fault you’re noncommunicative (and judgmental). It may sound harsh but think about it. You’re going into a date assuming the other person won’t be open to your perspective. You’re walking in, figuring they won’t like you for who you are, so you feel like you should put on a false front.

When we’re trying to “seduce” someone, we’re deceiving them in a way. We’re convincing them to go to bed with us (or to love us). What if we thought about it in more honest terms? What if we stopped attempting to charm the pants off our date, and instead we told them how we felt? What if we were intimate with them through honesty?

You may be surprised at what happens when you start to behave honestly and openly on dates. What’s the worst that could happen if you began to call out your dates when they did something you didn’t like? Imagine if you were clear about your expectations, what you wanted, and what you needed from someone else.

Often, we take dating so seriously. This comes back to this delusion that there’s only one person out there for us.

If we’re looking for the ONE, we may believe we only get a single chance with one person. If we blow it, that’s it, and we’ll be alone (and unfulfilled) forever. What a sad scenario—no wonder we put so much weight on our dating experiences!

When we shift our mindset to believe there are plenty of people we could connect with, and some we could even form a partnership with, it takes the pressure off. The pressure is alleviated even further when we realize it’s not up to our date to boost our self-esteem, make us happy, or whole. We find fulfillment and purpose with ourselves.

So, if the pressures off, start letting the truth out! Say what you think. Order what you want to eat. If you think your date’s being a jerk, say so!

View dating like a playground. We get plenty of opportunities to meet new people and connect. We will have fun as we test out engagement in this great big sandbox. We will see what feels genuine, what meets our yearnings, and what satisfies us. Approach dating like a game—not a deception, but an experiment!

Dating is All About Give and Take

Women (and sometimes men) often fall into the role of emotional caretaker on a date. They’re sensitive and open. They listen, rapt (or pretending to be), as their date waxes on about how great he is. They stroke his ego and let them emotionally barf all over them.

Years ago, a mutual friend suggested I start dating Judith. This was after seeing her at a party. I’d watched her talking to a guy spill his guts out on her all evening. She listened but couldn’t seem to get a word in. Judith is a great listener, but she’s often not a big talker.

I said to my friend, “You want to fix me up with Barbara Walters?!”

My friend said, “I think you should tell her that’s what you think of her.”

When we went into our first date, I said, “This is going to be a mutual conversation of give and take. I don’t want you to sit there and listen to me just to feed my ego. I’m not going to be one of those guys who is going to barf his emotional guts out on you like at that party.”

Judith said, “Well, you’re not going to be the asshole that you were at that party, either.”

And that’s how our first date began. We’ve continued to operate in honesty. That means, if one of us doesn’t like what the other person is doing, we don’t tiptoe around it. We say it. We obey the Rules of Engagement as outlined in our book, The Heart of the Fight.

The Rules of Engagement are:

1. Accentuate the positive.

2. Minimize the negative.

3. No one gets more than 50 percent of the blame.

4. You each get 100 percent responsibility for your happiness and satisfaction.

5. Express and agree with the truth, always.

6. Fight for, not against.

7. Assume goodwill.

If you want to get something great out of any relationship, whether you are friends, colleagues, spouses, or dates, you must get honest. You can’t hold back your feelings or sugarcoat your needs for the other person. You want something amazing, but you don’t want to be vulnerable or make the wrong impression. Fight for, not against the relationship, but don’t avoid the big stuff.

Instead, say what you’re really thinking.

If the date ends early, so what?!

You may discover all those bad dates in the past weren’t the result of dating boring people (you might even realize YOU were the boring date). You weren’t engaging and expressing yourself honestly to your dates.

So, if you’re sick of dating, remember, dating should be fun. Think of it like a big game or an experiment. Go in with an open mind and a commitment to be 100% truthful. You may be surprised at how much more interesting and exciting your dates become!

For more on engaging with others, please visit the Wright Foundation. Join us for an upcoming More Life Training, where you’ll connect with others on their transformational journey. We’re also pleased to announce our courses are available for download at a special introductory price. Learn how to strengthen your relationships, hone your leadership skills, and build the life of your dreams!

The Wright Foundation for the Realization of Human Potential is a leadership institute located in Chicago, Illinois. Wright Living performative learning programs are integrated into the curriculum at Wright Graduate University.