Not Enjoying Dating? It's Not Them, It's You

Not Enjoying Dating? It's Not Them, It's You Hero Image
Photo: Hillary Fox

When it comes to dating, people love to complain. Whether you’re hopping back on the horse after a relationship or have been patiently waiting, date after date, month after month, to meet "The One," it can be tough to actually stay present and enjoy the experience of dates themselves. Is the problem dating, or is it just a matter of how we approach it?

Yes, we've all gone on really bad (or just plain boring) dates, but the bigger problem behind the "dating sucks" mentality isn’t dating itself. In my experience, it’s about the limiting thoughts we bring to the process and how we respond to them.

So, for anyone out there who has ever thought, "Dating sucks!" I’ll offer some insight as to why you may be stuck in a negative cycle—along with some advice about how to rewire your expectations and tune back in to the present experience of your dates themselves. After all, dating really is just about meeting new people and exploring the possibility of connection. Here's what might be causing trouble:

1. Judging everyone against rigid expectations:

Everyone can relate to this one. All too often, I hear friends and acquaintances gripe about how dating can feel like a waste of time. "Why did I waste a free night with someone who could never be my future husband?!"

Trust me, I’ve been there. It’s natural to show up to a date wanting the person to conform to your expectations of what An Ideal Partner should look like. But the irony is that our "ideal" criteria tend to cloud our perspective and keep us from actually being open to the people right in front of us. If you’re finding yourself not enjoying the process of actually meeting new people on dates, ask yourself what expectations you’re bringing to the table. If you can shift from expecting every date to be a home run and instead shoot for a solid single, you’re bound to be pleasantly surprised more often than not.

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2. Showing up to the date thinking about the future:

This one is related to No. 1, and of course, the reason behind all of these anxious thoughts is natural. A lot of us would love to go on a first date with someone we could imagine dating seriously in the future.

But the problem with being fixated on the mythical future—that trip to the mountains, the party next weekend, the question of when you will sleep together—is that it totally prevents you from being present on your first date itself. How could you enjoy taking a walk with a new person and getting to know them if your brain is 50 million miles away in the mountains, worrying about an experience that has yet to come?

If you find yourself doing this often, take a step back, and try to settle your attention on your date itself, and the experience you’re having at the moment. A mentor once told me, "Focus on what’s now, and what’s next." By focusing on the present, you’ll be way more open-minded, curious, and excited—and who knows? You may find you actually like the person enough to invite them to the party next weekend!

3. Not asking honest questions about what you're looking for:

When I think back on some of my bad dates, I attribute most of them to being dishonest with myself about what I was looking for or not honoring my deal-breakers. Often, we can dupe ourselves into going on dates with someone who is actually totally misaligned with what we’re after—and of course, the outcome never feels great.

When you show up to a date, it’s important to do your homework. What must-have qualities are you looking for in a partner? What are your deal-breakers? What are some red flags you want to be on the lookout for?

Being authentic with yourself, and others, about who you are and what you are looking for is one of the most important (but also challenging) aspects of dating consciously.

Whether you’re going on dates with someone you met online or IRL, it’s crucial to know what you want going into the date. Get in touch with your values and priorities. Ask them questions up front and be honest with how you feel about their responses! Remember, no one is "right" or "wrong"—they might just have different priorities than you, and that’s OK. It’s your job to parse those things out so you can avoid mismatched intentions.

4. Putting your ego before your emotions:

Ah, the ego! It loves attention, doesn’t it? Many people I know—me included—are often drawn to dating because it scratches the itch we all share to be liked, to feel attractive, to be the object of someone else’s attention.

Don’t get me wrong: These things are all good if they also jive with where you’re at emotionally.

If you’re finding that you don’t enjoy dating right now because you simply would rather be with friends, family, or by yourself—then, by all means, do your thing! If you need "me time," take it. Don’t get caught up in the dating rat race just because your ego likes the attention…

5. Not being honest when there's not a connection:

You go on a date with someone who is great on paper. They treat you well, maybe you even have stuff in common. But for whatever reason, there wasn’t a spark. We’ve all been there.

Sometimes, the hard part is being honest about that. I think we’re all inclined to believe that there’s something wrong when we don’t feel a connection—as if it’s our fault or we’re failing to recognize something about the other person. But the bottom line is that feeling connection is very intuitive. If it’s there, you’ll know—and if not, well, you’ll also know.

You owe it to yourself AND the person you went out with to be honest and kind about where you’re at. Rather than "ghosting," always be straightforward and tell someone you’re not up for a second date. Simply "keep it real" and tell the person something like, "It was great to meet you, and I think you’re awesome. But I didn’t feel a strong connection, and that’s something that I’m looking for."

6. Comparing your date to past partners:

It’s never a good idea to fixate on the past—especially when you’re on dates with new people. The most fun and engaging part of dating is the opportunity to meet new people, explore the possibility of connection, and to feel greater space and inspiration in your life as a result.

If you’re on a date wondering whether or not the person will "live up" to the role of an ex, then you’re bound for disappointment. Whatever the story is/was with your past partner, it’s important to simply not go there when you’re going on dates. And if you feel like that’s not possible, it’s probably a good opportunity to examine whether you’re ready to be dating new folks, anyway.

7. Looking for the bad in others:

This one’s related to No. 1, and the first step for both is realizing that it’s happening. If you’re showing up to your dates with a metaphorical microscope, ready to dissect the other person from top to bottom, then you’re setting yourself up for failure. After all, we all have flaws. Plus, as social creatures, we’re all likely to act like worse versions of ourselves if we feel like we’re being judged. As Carl Jung said, "What we resist, persists."

Instead of focusing on the bad, can you use your dates as an opportunity to ask questions? If a person’s quirk jumps out at you, ask yourself why! What about it catches your attention? From a place of curiosity, you’ll be more likely to see the good in people—and get something out of the experience, even if the person’s not "a keeper." Another way to shift this mindset is to focus on a great quality in the other person because it helps you call in more of that quality in people you meet in the future.

By homing in on the thoughts we’re bringing to the process of dating, we can actually shift our attention so that we’re more open to seeing the positive—in others, in ourselves, and in the experiences we have in the present moment. For more, check out the dating app I created, MeetMindful.

Want more insight into your relationships? Find out the five things couples who stay together do every day and the ways your sex life can show you what's wrong in your relationship.


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