Whenever the topic of dating comes up amongst my friends, I’m always struck by the number of them who hated the process of dating. They couldn’t stand it: the frustrations of trying to find the right person, the disappointment of another “close-but-no-cigar” first date that went absolutely nowhere. Even worse were the near-misses, the people who seemed amazing but disappeared into the ether after a handful of dates, or the Crouching Stud, Hidden Douchebags who seemed great at first glance but proved to be assholes in disguise. There were the dates that were so bad they crushed the soul, the long parade of assholes, game-players and just plain toxic individuals who would be better off buried in unmarked landfills inscribed with dire warnings to alert future generations to the dangers.

Now I’ll be the first to tell you that dating is hard. It can be frustrating and time-consuming and there will be dates that make you believe that the dating pool needs a Herculean dose of chlorine before you’ll ever step foot into it again.

But at the same time, it can be fun. And, in fact, it should be. You can’t insulate yourself against dating’s inherent frustrations, but you can learn how to make dating enjoyable again.



If It’s Not Fun, It’s Going To Suck

Dating for me was a struggle for a long time. In the bad old days, I couldn’t even approach the women I was interested in and tended to rely on the Platonic Best Friend Backdoor Gambit as my way of trying to get laid or find relationships. After I’d started with the pick-up community, I had some successes, but so much of my self-esteem and sense of self-worth was tied up in my performance as a pick-up artist that every single woman I would talk to became a referendum on my value as a man. I would be so focused on my immediate goal – getting her into bed – that the whole process felt mechanical; it was an if-then-else flow-chart as I tried to direct her down the path that would end with us making out in the corner of the bar before heading back to my place for 30 minutes of squishy noises followed by the awkward “does she stay the night or should I call a cab” conversation.

Every night out became exhausting. I’d be going home feeling like twenty pounds of crap in a ten pound sack, carrying the tattered remains of my ego back to my car in the single man’s equivalent of the walk of shame. Every conversation with a woman felt like trying to make a dungeon speed run; I wanted to get through everything as quickly as possible so I could get to the end boss and find out if I was getting lucky or not that night. Instead, I was enduring that frustrating moment when you find that one point in a video game you just. Can’t. Get. Past. and playing it over and over again.

Small wonder I wasn’t improving as fast as I’d like; I was making myself miserable and turning every night into a trial.

When you’re doing something you hate, you don’t perform at your best. You try to get through it as quickly as possible instead of doing it as well as you can. It becomes the emotional equivalent of trying to perform ballet while tensing every muscle in your body at the same time. It’s theoretically still possible, but it’s going to be more difficult by orders of magnitude because you’re going to be fighting against yourself. The less you’re enjoying the process, the more that it’s going to show through your body language, through the way you talk to others, even in the way you think. Everything about you is going to radiate “unhappy”, and your potential dates are going to pick up on that.

So let’s look at some of the things that make dating more fun.

Be Positive

One of my friends has been back on the dating market for a few months now and has been consulting with me over some of her dates. One of the things I’d noticed right off the bat was the way she was approaching each night’s date: “Well, this is going to suck…” And, like clockwork, it would. The conversation was stilted and awkward, his flaws were magnified and getting through the date was a trial instead of a fun evening out.

I couldn’t blame her for having a less-than-optimistic outlook in general – she was coming off a quasi-abusive relationship, one of her dates was refusing to take “go away and don’t talk to me again” for an answer and 99% of the messages she got from OKCupid were about her tits – but the negative outlook she was taking into any date, even ones with guys who seemed perfectly charming, would quickly become a self-fulfilling prophecy. She was expecting to be disappointed and so she was keyed up to find whatever thing was going to ruin the night or prove that this was just another in a long line of assholes and social maladjusts that this was all that she could see. When you’re looking for flaws, you’re going to find them after all.

Negativity in general is an unattractive trait. When it’s directed inwards – through low self-esteem or a need for external validation – then you’re telling other people that you’re not worth dating; after all, if you don’t like you, why should they? When it’s directed outwards – when you expect to be disappointed or hurt, when you’re looking for the negative – then you come across as unpleasant and not fun to be around. Grumpy Cat makes for an excellent meme, but in person, someone with that attitude would quickly become exhausting. Dr. House is fun to watch on TV, but we like him because we’re at a step removed; we don’t have to put up with his constant snide remarks or relentless cynicism on a daily basis.

Part of making dating more fun means deliberately reframing situations for the better – forcing yourself to look on the bright side of things. A getting rejected isn’t the end of the world, it’s one less person you don’t have to focus on; you know how they feel and you’re free to move on to find someone who digs you. A bad date can be more proof that you’re going to die alone or it can be something to laugh about with friends later; one of my favorite bad dates ended up with me following a woman around Austin looking for her coke dealer. A willingness to laugh at the absurdity of it all can make the difference between something being soul-crushing and just another anecdote to share when you and your future snugglebunny are swapping war stories.

Maintaining a positive outlook is a habit; the sooner you cultivate it, the easier and more relaxing you’ll find dating to be.

Let Go Of The Future

One of the most important things in dating is to be willing to be outcome independent.

It’s a little counter-intuitive; after all, the whole point of dating is the outcome, no? We all have something we’re hoping to achieve, whether it’s getting laid, finding someone to settle down with or even simply getting a second date. The problem is that by focusing on that end goal, we miss everything around us. We end up so wrapped up in whether or not this person meets our criteria that we end up psyching ourselves out. The more goal-focused you become, the more you get anxious about meeting that goal, which puts absurd levels of pressure on you. You’re no longer flirting with somebody, you’re desperately trying to rack up another achievement and if you don’t play it perfectly, you’re going to blow it forever.

Being outcome independent is incredibly liberating. You no longer spend each date wondering about whether there’s a potential future or what this might represent, and you can just relax. It might go somewhere or it might not and that’s ok. You don’t need to worry about making sure this interaction “succeeds” because you’re free to just enjoy it.

It’s the ability to just enjoy a date for its own sake that’s critical to avoiding dating burnout; it’s easy to get frustrated when each date is another two to four hours of your life spent not getting any closer to getting what you want. It’s another entirely if you are just looking to spend time with somebody new and interesting, even if it never goes anywhere past that night. They may not be your soul-mate. Hell, they may end up being somebody you wouldn’t normally go out with on a bet. But if you can just see your date as another experience to be savored, even if it’s just for the stories later, then you’ll be surprised how much more enjoyable it can be.

And besides: you never know where even a supposedly “failed” date might end up.

When we focus on goals we tend to narrow our outlook based on preconceived notions and assumptions: this person couldn’t possibly be a future spouse for me, they’re just a one-night stand. I’m not going to meet anyone at this pick-up bar, everyone’s just looking to get laid. This person’s nice enough, but they’re not my type, I should just end things now. Except many incredible relationships start off as one-night stands… they just become one-night stands that never end. There are people at that bar who are just like you, looking to meet and start a relationship with somebody awesome so they never have to go back to that bar again. That date that didn’t quite work out might end up being a valuable friend – possibly even someone who could introduce you to the person who is perfect for you.

One of my favorite quotes on this matter comes from the master:

“Don’t think. Feel. It is like a finger pointing out to the Moon, don’t concentrate on the finger or you will miss all that heavenly glory.” – Bruce Lee

Dating is as much about the journey as it is about the destination. Focusing entirely on the end of the journey and getting there as quickly as possible means that you miss all of the incredible scenery and adventures you can have along the way.

And while we’re on the subject of outcome independence…

Simply Connect

All too often, we go into a date with preconceived ideas of what we’re hoping to get out of it. Sometimes we treat it like something we need to endure to get what we want. Other times, we go in feeling like we’ve got something to prove – we have to demonstrate our worthiness to this person in hopes that we can see them again (or see them naked…). We go in trying to mark off the checklist of relationship must-haves, watching for our deal-breakers, running down our strategies of how we’re going to get them to like us, how we’re going to get them into bed.

What we don’t do often enough is go into a date simply looking to connect with another person. It’s easy to get caught up in what they represent – another potential disappointment, a spousal candidate, a chance to escape a dry-spell – that we build up our expectations and lose sight of them as just another person and connecting with them on that level. We want to find out more about them – what drives them, what they are passionate about, what makes them special, what do we have in common with each other? While it’s good to have standards (up to a point), slavishly insisting that potential partners must meet EVERY one of them can blind us to their other qualities that might make up for not having attributes that we would otherwise require, or finding out that what might be a deal-breaker with any other person is an acceptable price of entry for this relationship.

You’re not dating a list of attributes or an abstract representation, you’re dating a person.

Remember: They Want Your Date To Succeed as Much As You Do

It seems obvious but occasionally it needs to be said: nobody goes on a date thinking “Man, I hope that this is some jackass who’s going to waste two hours of my life! I can’t wait to reject him!”

I’ve seen far too many guys who treat a date like a military campaign; they plan out everything with the idea that a woman’s default position is “no” to anything and they have to fight to change her mind right from the get-go. Small wonder then that they don’t get a second date. Nobody appreciates being treated like an opponent, especially when they’ve already signaled that hey, they’re kinda interested in you. While folks may have occasional bouts of cold feet or second thoughts, if they’ve agreed to go on a date with you, they want it to work too. They’re not looking to see if you’re going to leap through hoops for their amusement. They’re not looking for an opportunity to break somebody’s soul into a thousand pieces. They’re hoping to have a good time and realize that they’ve just met somebody awesome just as much as you are.

You don’t need to try to impress them or overwhelm them by being the most entertaining person they’ve ever met. You don’t need to be perfect; most people are going to forgive the little screw-ups and imperfections because they’re just as worried that they’re going to spill something on themselves, say the wrong thing or fling their silverware across the room. You need to just let yourself relax. Enjoy building the chemistry. Get to know them without pressuring yourself to feel like you need to put on a full song and dance routine in order to get a second date. Some dates are magical experiences where you feel like you’re meeting somebody you’ve already known for years. Some will go nowhere. Some will be people who are so wrong for you that you’ll be amazed the two of you don’t spontaneously combust just by being in the same room together.

Let yourself have some fun, and you’ll find dating to be a more enjoyable and memorable experience, even if it’s after the fact.