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Online Dating: Avoiding Witches and Flying Monkeys

Updated on June 5, 2022
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Mike Shoemake is a former worship leader and youth minister who grew up as the son of an Army chaplain.



Dating is not easy. I think, for most of us, this is an understatement. Those of you who were divorced after years of marriage may have experienced the silent shudder of realization as you considered the prospect of walking back into that land of suffering and apparent desolation. Dating really is a game of persistence and endurance, but there also is a fair amount of strategy involved. For some of us, dating basically amounts to a dice roll. Every so often, you cross your fingers and roll again. This model certainly has the advantage of being simple and uncomplicated to put into practice. For others of us, loaded dice are an absolute necessity. If we can't play with loaded dice, we'd rather not play at all.

Some of us would love to go dating with a checklist of requirements, 5 pages worth of essay questions, a background-check consent form, and a well thought out contract to be signed at some point if things appear to be working out. The disadvantage here is that most prospects will disappear the moment we flash the dog-eared stack of paperwork. Those that remain are almost certainly not who we're looking for anyway. At least with the dice roll, there's no documentation to scare them off.

Some of us have simply stopped rolling because we've experienced enough failure to decide that it's just not going to work. Maybe it works for Jim or Jane, but it won't work for me and my needs. The good ones are taken, I don't have enough to offer, etc. As we look out across that barren wasteland, off in the distance is a city on a hill. The billboards say it's great but of course they would. That's their job. The people who have been there apparently don't want anyone to know about it, and nay-sayers stand along the road with signs of protest. But in the distance, you hear music playing and you wonder if maybe this is the place for you. As you listen more closely to the music, you realize that it sounds an awful lot like munchkins.

The Yellow Brick Road

So what is it that makes online dating work or not work? The answer is you, although I understand that this is an uncomfortable and irritating thought. The truth is that you will experience a lot of failure in the dating world. It really is trial and error. You can ignore the failure and keep doing the same things, or you can examine your part of the failure and make adjustments. If we can ignore the idiosyncracies of those who irritated us for a little while, it's incredibly advantageous to recognize our own issues and actually deal with them. When we do that, failure becomes our friend. Each failure is another learning opportunity and another step towards the goal you've set for yourself.

As we look off toward that city (you know, the big green one), we notice that there is a road that takes us right up to the gate. And behold, the road is paved with large, yellow bricks! Along the path are some key stops for us to help us be successful on our journey. You could skip one or two, but I wouldn't recommend it. You might actually be surprised to learn that you've been setting yourself up for romantic pain and suffering all this time.

First Stop: The Medical Station

While none of us have come through life completely unscathed, some of us have been through especially difficult times. Maybe for you these are recent events. When you start dating, it's really not a good idea to carry unprocessed baggage into a new relationship. Dating is hard enough on it's own. Open wounds from divorce, sexual abuse, physical abuse, emotional abuse, or other traumatic events will definitely derail your attempts to find love.

Often this is because we compensate for the trauma in ways that are not healthy or helpful. We find ourselves unable to trust and become controlling, interrogating, micro-managers. Our anxiety causes us to constantly assume the worst and freak out over little things. Or maybe we're so afraid of conflict that we keep everything inside until one day we just disappear for seemingly no reason. Fear of commitment, fear of intimacy... These are issues that will sabotage your attempts to develop a long term relationship. If these are things you struggle with, I strongly suggest that you invest in your own healing somehow (preferably counseling) before you start actually dating. Otherwise, you're likely spinning your wheels and creating more sad stories for yourself.

Second Stop: The Radar Station

Does it seem like all of your dating options can be categorized as either witches or flying monkeys? Maybe you find yourself attracted to people that you know are bad for you. We all have a radar that goes off when we get close to someone we find attractive. For some of us, this radar is not tuned correctly. Do you consistently pass up the nice guy in favor of the bad boy only to find yourself hurt again? Some of us have an uncanny ability to pick out the people who will ultimately mistreat us, cheat on us, lie to us, etc. Nice guys are boring, bad girls are sexy, etc. If this is your pattern and you're tired of where you always seem to end up, now would be a good time to revise your model. What is a dud really? Maybe your definition of that word is part of your problem.

Some of us just need to be more discerning (ie. less gullable). Be skeptical of anyone you meet on a dating site who asks you to bail them out of a crisis financially. I exchanged emails with someone on who turned out to be a predator with a sob story about how she had gone away to some foreign country as a missionary, both of her parents were killed by the natives, and now if I will give her money for a plane ticket to get out of there she'll comes back to the states and we'll live happily ever after. While I've bumped into many predators on and SinglesNet, I never saw one on eHarmony or Chemistry. Both of those sites require a fair amount of overhead which make it less ideal for people who aren't interested in real relationships.

Third Stop: The Armory

Dating absolutely requires protection (and no, I'm not talking about safe sex). Too bad no one has come out with condoms for the heart. The bottom line is that the dating process is full of negative messages that we can internalize. When someone walks away from a relationship, it doesn't say anything about either of you separately. It just says something about the two of you together. It doesn't mean that person #1 is a heartless scumbag any more than it means that person #2 is unloveable or a loser. These two people simply don't belong together. Out of the millions of options out there for them, both parties can say "Well, that's one down..." While we may recognize this is true intuitively from the outside, it's incredibly hard to remember in the moment.

One danger of dating sites is premature attachment. Dating sites are a way to prescreen your dating prospects and to get an idea about fit, how well you might click, etc. But, what you see in Q&A or email or even on the phone is not necessarily what you get. In fact, I’ve heard that most people don’t let their guard down enough for you to completely see who they are, warts and all, until a year into the relationship. Attachment should build over time as you learn more about who they are, and actions (not words) are the best indicator of who they really are. It's just not a good idea to attach emotionally to someone you haven't even met yet. Save your terms of endearment until after you've actually spent some time in the same room. Be wise, guard your heart, and go slow emotionally. This is an important principle for all types of dating–-not just dating online.

Fourth Stop: The Lookout Station

I strongly suggest you hire a relational lookout. Find someone who is wise, insightful, and trustworthy. Ask them to walk with you through this dating thing and to let you bounce things off of them. Once you've done that, be transparent with them and allow them to help you. I believe that we're the most myopic when we're dating. It's a terrible time to try to go it alone. Really, really stupid ideas make enormous sense to us when we're in the middle of the endorphin haze. Wise counsel can be critical to not walking away with regret.


While there are detractors of online dating, I respectfully disagree. People you date are strangers no matter how you meet them (online or otherwise). Dating sites give you an opportunity to screen your dating prospects before you actually see them in the flesh. Some sites help you find compatibility in more of a scientific way, while others give you search options so you can do it yourself based on shared interests. You can read their profiles, ask them short answer questions, and drill into things like faith, values, integrity, interests, communication style, family relationships, etc. It helps you make the actual dates count as much as possible. For those who are tired of going on dates with people who aren’t even close to compatible, it’s a great tool. It's just a tool that should be used wisely.


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