How To Put The Fun Back In Dating

When I was a teacher, a lot of my colleagues took the view that if the students were having fun, they couldn’t be learning! I sometimes kept my view of such asininity (yes, that’s a word) to myself, because I honestly can’t think of a dumber view of learning! The reality is that research shows the opposite is true. If you absolutely hate what you’re doing, not only will you resist doing it, but you won’t learn anything from it.

And, this is why most people hate dating in 2019: we have taken all the fun out of it, view it as an arduous and gigantic pain in the ass, and then wonder why it is so horrible.

But, I argue that dating actually can be fun, if we just “get out of our own way,” and start thinking differently about dating. Below I list a few ways to do just that!

Stop Pre-Screening So Much

couple riding a bike togetherYou may think pre-screening is a good idea, and I do suggest some degree of “gate-keeping” to keep out the worst-of-the-worst (like felons, scammers, etc).

However the problem with pre-screening is that it takes out a lot of the potential fun and connection of dating. Think back to the fun times you’ve had romantically. Now, think of how many of those people you never would have met in 2019 because you probably would have pre-screened them because they: were too short, too overweight, too old, or too young, didn’t open with anything clever, “are not going anywhere,” didn’t look like they’d take good couples photos you could show off on social media, etc.

Part of the fun of dating involves mystery and intrigue, and the chemistry that can come from this. Pre-screening eliminates a lot of this element of dating. It also usually selects for the most boring “guy or girl next door” type who may seem really good on paper, but in reality may be a lot less fun, exciting, and fulfilling than you think.

Stop Inventing Red Flags

Let me tell you a romantic story. You saw him at work. He caught your eye immediately. Something about his personality just made you take notice. His cute and slightly nerdy style wasn’t your normal thing, but somehow it made you think about him even more. His smile when he said “hi” for the first time gave you butterflies, and you couldn’t stop thinking about him after that.

However, the next day you heard him say that he isn’t sure what he’s looking for in a partner and isn’t fully sold on the idea of marriage. You can’t be dating someone who has no long term relationship goals, and at 31 you definitely want marriage. So, you decided to quit talking to him and are talking to a guy on Bumble instead, who met most of your filter requirements, but even though you aren’t really attracted to him, he said he’s probably up for marriage, so you’re rolling with it.

Now that’s romance!

Ok, yes that last sentence was sarcasm, but hopefully you can see why this way of viewing dating is particularly awful. I totally get observing actual red flags, like if the guy said his last home was Riker’s Island or he’s a polygamist cult leader. However, in this example, the guy didn’t say anything definitive and may actually like our story’s main character, and may even like the idea of marrying her at some point. But, she invented a red flag where there wasn’t one.

Break Your Pointless Rules

man lifting woman in silhouette at nightThis is probably the biggest reason dating is awful in 2019. We have created so many “rules” that nobody ever stops to question whether they are useful. You would be shocked how many people (women in particular) will start a sentence with “he is so amazing and I really like him…” and then explain why they can’t date him because he is outside some sort of personal rule they set for themselves (or, more likely, society has told them they should set for themselves).

Often it’s followed by “…but he’s younger than me” or “…he doesn’t have a college degree.” In many cases, people refuse to date a colleague (even if there is no official company rule against it) or convince themselves that they can’t ask out that cute guy or woman who checks them out at Starbucks every day because “you can’t ask people out who are working.”

Then, after obeying these rules, they’ll go online and complain they can never meet anyone good and that dating sucks.

You know what? If an arbitrary rule causes dating to not be fun for you, then ditch the rule. It’s as simple as that. Also, ask yourself who comes up with these rules? The answer is probably people who are miserable!

A Date Is A Connection, Not A Job Interview

Another reason dating sucks for most people is because dates themselves are boring events that are more like job interviews than something fun.

I don’t like dinner dates as first dates for this reason. I’m not a big fan of coffee dates either. Alcohol ones aren’t as bad simply because a few drinks can loosen people up to have some fun. When you get people together to simply sit and talk, most people treat it as a back-and-forth session designed to “interview” the person as to whether they would make a good long-term partner.

Besides being boring, the main problem with this method is that it is horribly ineffective. Someone who gives perfect answers may make an awful partner, and someone who doesn’t answer perfectly could turn out to actually be the best partner ever. And, that’s assuming you are even asking the right questions!

So, instead I plan dates with the goal of making an emotional connection and actually having a lot of fun. Yes, you heard me right. Having fun is the goal. And, when you’re having fun, you’re more likely to make a connection.

Go do something fun, like a concert, miniature golf, or mountain climbing. Run a 5k together. Do something that will be fun and will help you connect. And, if you feel that connection, go on a second date, even if your “find a red flag everywhere” sense is tingling a little.

Good Enough is Good Enough

african american coupleYou can make dating fun again by getting rid of insane perfectionism. I once learned about a woman who had a requirement that a guy must have never have “peed outside.” Yes, you read that right. Any guy reading this knows that this probably disqualifies most guys on the planet.

Where this came from, I have no idea. And it’s pretty extreme, but when dating and choosing a potential partner, remember that “good enough” is good enough. Many people search for perfection and miss great people as they search for “perfect.” They also miss out on great date opportunities, fun nights, and even friends.

Statistically speaking, perfection doesn’t exist, and if it does, the odds are stacked against you. Looking for a single guy over 6′ who has an athletic build and also has a college degree? Statistically the first requirement alone eliminates nearly 90% of men. The college requirement eliminates about 60%. And if you look at obesity stats, such a guy is even rarer. You start combining these requirements, and you may be looking for a person who is less than 1% of your local population. And, guess what?  You’re competing with a lot of others also wanting him or her, if that person is even single (statistically also unlikely)!

Get Offline

social media apps on phoneOnline dating makes a lot of the previous issues worse. Dating is fun when it’s about making a connection to a fun and interesting human being. Online dating makes dating about logical filters, common interests, and evaluating a person based on a few photos and a brief profile. It also encourages dialogue that defaults to boring, fact-based interview questions.

I believe online dating has a place in the modern dating world. However, I also believe that people use it as a crutch. One night my friends and I were hanging out at a local place. Two women were sitting next to us. They were on Tinder. Despite being around a lot of eligible people having fun, they were loudly and rudely criticizing guys on the app.

Personally, my friends and I were not interested in these women, but I’m sure some guys in the place would have enjoyed talking to them. So, rather than opening themselves up to that, they chose to look at guys on an app they didn’t even seem to like anyway. I don’t think I have to explain why looking at profiles and hating it instead of talking to people around you isn’t fun!

Online dating may allow you to swipe in the comfort of your own home, but that’s also a pretty boring way to go about it. So, even if you use online dating, opening yourself up to offline social opportunities and dates will likely make dating more fun and exciting.

So, if dating is a horrible chore, remember that it doesn’t have to be! So, let’s make dating fun again!

About the Author

David Bennett

David Bennett

David Bennett is a relationship expert, and has been a dating and relationship coach for over 8 years. He is listed in the top ten personal coaches for 2019, and is the author of seven self-help books. He has been featured in over 400 publications and other media appearances, including The Chicago Tribune, The Boston Globe, Men's Health, Bustle, Prevention, and Woman's Day.

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