In Defense of Dating

Dating is scary. No doubt about it. Whether you’ve been in a relationship for a while, just gotten out of one, or are brand new to the scene, there’s a never-ending list of obstacles and questions to keep you up at night: “her laugh is a little weird,” “he spends all his time playing Call of Duty,” “is she sick of me yet?”, “when are we having a DTR?”, “why hasn’t he held my hand yet?”, “is it time to start talking about marriage?”, “why are there no good men?”, “why are all women crazy?”, “why are we having another DTR?”, “what’s a DTR?”

Now, I’m not claiming to be an expert on this subject, but I’ve been around long enough and have had enough personal experiences and interactions with friends currently in the dating pool – a horrible metaphor that needs to stop, by the way – to identify a few avoidable trends that, for lack of a better word, cause dating to suck (emphasis on the word avoidable). We can make dating awesome again, if we can just keep a few important things in mind.

Stop Making Deal-Breakers of Small Details and Vice Versa


Take for example the story of a couple who we’ll call David and Jenny. On paper, David and Jenny had all the right things in common: they were both good looking, driven, athletic, and incredibly family-oriented. David was funny. Jenny was completely genuine. Each person had exactly what the other was looking for in a partner and eventual spouse . . .

. . . except David was about an inch and a half shorter than Jenny, a professional volleyball player (that means, pretty tall . . . or pretty/tall, as it were). Believe it or not, for Jenny, this was more than a big deal; it was an existential crisis! “I’ve always dated guys who are taller than me,” she anxiously recalled. “If I date David, I can’t wear heels anymore. If I marry David, we’ll have short children. But he’s so cute. What am I supposed to do?”

Jenny experienced what we in the making-up-new-medical-terms community refer to as dating myopia, a fallacy in which one small, insignificant detail about another person outweighs everything else. This is not to be confused with common sense, in which the detail is actually significant (e.g., he’s an actual Nazi. She stole my kidney. You know.). Put yourself in Jenny’s shoes (or flats): you’ve met someone who seems to check nearly every box on that conceptual list that we all have – except for one. Maybe it’s you don’t feel “romantic feelings” yet towards that person, or he has freckles, or she has man hands, or maybe she’s not blonde, 5’5″, and a size -4. BUT EVERTHING ELSE CHECKS OUT!? Are you kidding me??

Look, we live in an imperfect world. If you find someone who is nearly perfect, it’s okay, even preferable to round up. My mother thought she wanted to marry someone who could sing and dance; my father, a tall blonde. They both got the exact opposite of what they thought they wanted. Were they disappointed? Well, 37 years and six kids later, they’d probably tell you they’d do it again.

(Speaking of marriage, you ought to know that Jenny was big enough – pardon the pun – to look past David’s height, and the two are to be married next month.)

Have a Plan*


I qualify the word plan with an asterisk because of the following hypothetical, but not uncommon, story: James and Christine are thinking about dating. Each finds the other one attractive, and they both want essentially the same things out of life; however, both are hesitant to begin the courtship process, but for completely opposite reasons. Prior to dating Christine, James wants to be completely sure that this is what he wants, that it will lead to an eventual marriage, and a long and happy life. James wants structure, because therein lies control and security. Christine, on the other hand, sort of wants those things too, but is less eager to fix deadlines on her feelings or her personal growth. In fact, she’s a little unsure she’s wants all the same things as James – at least in the way that he wants them.

Neither person is necessarily incorrect in their approach to a potential dating situation. Dating, like marriage, represents an interesting balance between fun and work. There needs to be structure, but there also needs to be room for spontaneity. Work and fun are both needed for dating to be successful; if dating becomes all about fun, and expecting things to “just happen,” it may never develop into something that’s deeper and more enduring. It may never develop at all. But if dating purely becomes work and structure, overplanned dates, and meeting expectations, it leaves no breathing room for organic development. It becomes forced. On a similar note, If you keep employing the same rigid plan, going after the same kind of girl, etc., and the plan repeatedly does not work, the plan is flawed, and needs to change.

In my own experience, I learned that dating is more about contingency planning – learning how to react when things don’t go the way I think they should – than actual planning; it was the planning itself that became organic. Before I got married, I was a lot like Christine. I wasn’t too concerned with plans, so long as dating was just really fun. Unfortunately, as a couple of my dating relationships became more serious, I found myself continually unprepared to take any further action. I didn’t have a plan for life after dating, much to the chagrin of the great girls I dated as well as my own regret for wasting their time. I didn’t want to be tied to a structured timeline because I knew that as long as other people were involved, life was a gamble, involving risks and disappointments. But I had gone through too many bad breakups to be satisfied with dating without some kind of plan.

Finding that happy medium was not easy. But after receiving some timely advice from someone much smarter than me, I began beta-testing a “plan” of sorts with the next girl I dated. I kicked myself at its simplicity: if spending time with this girl makes me want to spend more time with this girl, then I should spend more time with this girl. If, however, spending time with this girl makes me want to spend less time with her, then I should spend less time with her. This allowed for fun, but it was fun that was going somewhere. And you know, the more we got to know one another, the more time we spent together. The plan was working. Of course we had arguments and disagreements along the way. But fortunately for us, we both saw those arguments as being productive and eventually bringing us closer together. Dating for us was work, but it was rewarding work. Engagement was a nightmare, but a thankfully short one. Marriage, really, is a lot like dating should be. It’s like graduate-level dating: we still have arguments, but because we still really love spending time together, the arguments get us somewhere. We’ve worked them into our plans.

You Are Good Enough . . . but Don’t Let It Go to Your Head


We live in an age that treats self-esteem like currency: How much do I have? How much do you have? Why do you have more than me? Where can I get more? Why am I spending so much of it on ice cream? Much of the difficulty surrounding dating has to do with self-esteem: either not enough of it, or too much of it. For this, I have two stories you’ve probably already heard. The stories of Hannah and Jacob.

Hannah doesn’t date much, but you know she really wants to. She’s one of those girls that doesn’t really fit the mold, and is therefore permanently friend-zoned. Maybe she’s awkward in social situations, doesn’t have a model build, or is even perceived as intimidating to potential suitors because of her paycheck, her candor, or the fact that she can bench press more that most guys her size. Thing is, Hannah is very datable, but for one reason or another, she doesn’t get asked out, which leads her to believe that something is surely wrong with her, which causes her to resort to some pretty unusual, even extreme measures to make herself “datable” by others’ standards.

Then there’s Jacob. He doesn’t date much either. Not because he doesn’t get asked out, or because he’s not a swell guy, but because he doesn’t really try. Doesn’t have time. He is perfectly content with living his life as a bachelor with his bros because things are less complicated that way. Plus, for Jacob, the dating sphere leaves a lot to be desired. It’s filled with girls who just want to get married, or who are crazy. Girls who don’t wear enough makeup, or too much. Besides, if he’s not sure that he wants to date seriously, why would he want to lead anyone on? Those girls are just better off without him. He just needs to play it cool, and save himself for the time when that perfect girl will come gliding into his life – and of course she will, because he’s such a swell guy. Right?

Both stories reflect a serious imbalance of power in our dating culture: ultimately, the guys are the gatekeepers of the dating world; it is their responsibility – no, their right – to decide who is allowed entry. And if girls try to take that gatekeeping position from the boys, they are immediately labeled as too forward, masculine, and unattractive. Not to say there’s no overlap. Physically less-attractive guys can be equally shut out by their more-attractive female counterparts, despite their best efforts to ask those girls out.

To this, let me restate the section heading to everyone: You are good enough . . . but don’t let it go to your head. There is not a thing wrong with self-improvement or making yourself attractive to a prospective partner, but don’t let your success in attracting dates determine your success as a person. You’re good enough without having to compete with unrealistic ideas of beauty, etc. Just because you don’t fit into someone’s mold of the ideal candidate gives you all the more reason to break it!

Prior to marrying me, my wife was a lot like Hannah, friend-zoned by many of the guys she liked because she didn’t look a certain way or act in a manner contrary to who she was. Of course, she experienced her fair share of self-doubt. But do you know what she did when we started hanging out? She asked me out! Or, more accurately, she sternly asked me why I hadn’t asked her out, so I asked her out (but we all know she really asked me out). And let me tell you, I will be eternally grateful that she did – because I was a lot like Jacob, completely oblivious to a golden opportunity right in front of me.

Guys, I don’t hate to tell you this, but if you end up dating someone who continues to feed your ego, who doesn’t challenge you, or doesn’t motivate you to change your thinking in some way, you’ve found the perfect woman chances are very good you’ll never really love each other. Real love only comes from sacrifice; you can’t really love someone you don’t serve in some way, and in dating, that service comes in the form of giving of yourself, your effort, and your desire to see the other person happy. If these things are not common to both parties, the relationship will fail.

There’s No Substitute for Real Dating


I mean actual, formal dating. Not group-dating, not simply hanging out, not texting. Dating. What do I mean by dating? Or love for that matter? Well, I’ll let my good friend Brak handle that one:

Real dating involves no more and no less than the two people relevant to the relationship; it’s two people alone doing what they love together. My first date with my future wife was three rounds of H-O-R-S-E followed by ice cream (which I had to buy because she beat me two out of three). It wasn’t necessarily creative or magical in nature, but it was the beginning of four solid years of arguing who has the better shot (right now it’s me), as well as mountains of ice cream (and this marks the third time ice cream has been mentioned in this post). We may not be the most lubby-dubby couple, but our marriage is built on things that are important to us both, simple as they are.

In dating, trying is succeeding! If you don’t know what you want, then go out there and at least figure out what you don’t want. If you’re absolutely certain of what you want, then go out there and see if that something really exists. The whole point of dating is to practice being around another person whose company you enjoy, and you can’t get that practice in any other way. The reason it’s called dating is because it is marked by a period of precious time. I’ve put in my 10,000 hours and so should you. Yes, it’s an unprotected investment of time, money, and emotion (and I can tell you horror stories of people who have lost big time on such investments). But if you’re willing to be a little braver than you think you can be, look past that inch and a half difference, put some kind of flexible plan into effect, and be completely honest with yourself, you’ll find that dating is not so scary or complicated as you once thought; sometimes, it’s just a matter of sitting down with someone to eat a salad and a big piece of beef.

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