What is it about love and money that causes people to make bizarre and often terrifying mistakes?

There are lots of other things in life that are easy to screw up. For example I am horrible at waking up. Most days I hit the snooze button until ten minutes past when I should which means I have to do the rest of my morning routine in a dizzying stupor.

This morning I forgot to set my alarm at all and had to do the whole thing in three-and-a-half minutes.

Daylight Savings Time is the worst. Last year I showed up at work an hour late one day because of it. I don't even know how I managed that considering I use my phone as an alarm and that sucker updates automatically.

But there's something about love and money that causes people to stop thinking logically and start pursuing bizarre romantic notions. If you're old enough you've probably lost at least one friend to a toxic relationship that never seemed to end. We all have an uncle or a cousin who has been roped in by a get-rich-quick scheme or a stock deal gone bust. And as some kind of cosmic joke most people who are afflicted with poor judgment in love or money never seem to get better. They keep repeating their mistakes over and over with the hope that it will be different next time. It rarely is.

I'm a big fan of Mark Rosewater's writing and I've long wanted to riff on one of his best columns: To Err is Human. If you haven't read it yet go check it out when you're done with this one. In it Mark shares some of his most memorable dating stories and likens them to mistakes he's made while designing Magic cards. While I've never designed a Magic card—not a real one at any rate—I've certainly had my share of dating stories. While thinking back on them the other day I realized that the lessons I learned from them are pretty similar to the things I've learned buying selling and trading Magic cards.

Coincidence? Possibly. But I'm always up for continuing to learn from the foibles of my youth. If I can entertain you in the process even better.

I've changed all of the girls' names so I don't embarrass anyone other than myself. The stories to the best of my memory are completely true.

Caroline

I met my first girlfriend at a middle school dance.

I was in seventh grade and puberty was in the process of turning my brains into mush. My friend Brooks had just scored his own girlfriend—a tall striking blonde—and I wanted one too.

Compatibility? Communication? Gender equality? None of those concepts meant anything to my fourteen-year-old mind. All I knew is that girls were mysterious smelled nice and were probably soft. These were all things that I wanted to know more about.

Unfortunately for me there wasn't an eligible female within a quarter-mile radius. Seriously: my home was in the backwoods of central Massachusetts and I went to school at a private all-boys academy two towns over. The idle childhood crushes from my days at public elementary school had moved on. I was marooned on an island of testosterone.

Every couple of months however our school had a dance. For that one glorious night our halls played host to the pupils of an all-girls school on the other side of town. These dances were notoriously awkward affairs; imagine taking the normal drama of the school dance and adding in the wrinkle of 'this is the only time you will ever see these girls unless you get one to go out with you based on something you do tonight.' For a weird gangly geek like me these dances were terrifying.

At the beginning of seventh grade my plan was to spend most of the evening psyching myself up and eventually ask one of the girls I found kind of attractive to have a slow dance with me. Since I was tall (six feet by sixth grade) I would usually ask one of the taller girls to dance and hope that she would say yes out of some misplaced sense of solidarity. The problem with this plan is that one of the girls I kept asking was the sister of one of the meanest kids in my school and he didn't take too kindly to my advances. If I wanted an actual girlfriend I needed a new plan.

Enter Caroline. Caroline was…unremarkable. She had a face full of braces and acne but so did I so who was I to judge? Her redeeming qualities were…heck I don't know. She was a girl and she liked me. I knew she liked me because she told my friend Brooks' girlfriend and she told Brooks and Brooks told me.

I asked Caroline out at the next dance and she accepted. On our first date both of our parents drove us to Bertucci's pizza and waited outside while we had lunch. I was so nervous that I accidentally left the entire $20 bill that my parents gave me on the table. For our second date we saw O Brother Where Art Thou. For our third I decided to take her to the movies again. Yeah I wasn't all that creative in the romance department.

And that's when everything fell apart.

Caroline and I would talk on the phone once a week or so but we never had much to say. I was scared to screw things up and to this day I won't even pretend to understand what she was thinking at any point during our time together. She seemed excited to go to another movie with me though so I decided to take her to some generic romantic comedy. That's what all girls like right?

That was also the first date where I was bold enough to put my hand around a girl's shoulder. I kept it there for the entire film and that small piece of human contact was such a thrill that I still can't recall the title or plot of the movie we saw.

The next day Caroline broke up with me.

She didn't even have the decency to do it in person. Brooks' girlfriend found me on AIM and relayed Caroline's message. When I pressed her for details she told me that Caroline thought I was a creep for inviting her to a movie that was 'all about sex' and for being 'all over her' the entire night.

I was crushed. Even though I had wanted a girlfriend for all the wrong reasons I still thought of myself as an honorable guy. Heck I had already started to develop the paladin complex that would plague my love life for the next eight years.

Even though Caroline and I had absolutely nothing in common and I didn't even really like her all that much the fact that she didn't want me—and thought I was some horrible creep no less—was too much to bear.

The Lesson: Get to know the person not the fantasy.

There are about a hundred different lessons that can be learned from my time with Caroline but this is the strongest. Through my entire 'relationship' with her I never got to actually know her as a person. If I had taken the time to do that I might have realized that she wouldn't have appreciated my film selection and forwardness. I might have even learned that we had nothing in common and had no business dating at all.

In Magic we all have fantasies—and they rarely come true. This is why it almost never makes sense to preorder cards.

Remember Skaab Ruinator? Even the most bearish financial gurus still thought this guy would likely see some play and I don't remember anyone thinking he'd fall to his current $1.49 price tag. I figured that his bottom dollar was $5 and he'd still be a great one-of in Birthing Pod decks. The general community consensus was that he had a real shot to be the flagship of his own archetype and stay in the $20 range.

Most of the time it makes sense to get to know a person—or a card—dedicating yourself to them. Fantasies are beautiful but at a certain point you have to be realistic. Successful speculation and successful relationships always need a solid foundation. If you get swept away with the hype you will find yourself blindsided.

Some cards do live up to the hype. It looks like I was too bearish on Tamiyo a planeswalker that I liked a lot in theory but didn't want to bet on. I still think I was right to think logically and conservatively back history instead of falling in love with a card I hadn't even played yet. When in doubt go with results and performance over theory and hope.

Mary

I wasn't sure that Mary liked me until the morning in Drivers Ed when I had to wear beer goggles on in front of the whole class. The teacher asked for a volunteer to help guide me in a straight line and her hand went up so fast I thought he was going to issue her a speeding ticket.

I had heard rumors of her interest before that point but when you're a lonely geek in his first year at high school you tend to assume most of that stuff came from a buddy who just wants to get you to make a fool of yourself in front of the wrong people.

At the end of class Mary asked me if I wanted to hang out for a bit. It was a Saturday morning so we had a couple minutes to kill before our parents came to pick us up. We ended up going down to the science labs in the basement and I remember her interrupting our conversation about parallel parking by asking me if I wanted to kiss her.

I didn't say yes—I just did it. It was my first kiss. Hers too.

The next day and a half was agony. I didn't get a chance to talk to her again until Monday morning when she asked me to ask her if she wanted to be my girlfriend. She accepted and we kissed a couple more times over the next few days. I was walking on air.

On Thursday she broke up with me.

I couldn't believe it. Had I done something wrong? Come on too strong again perhaps? Did my breath smell bad? Did I talk too much about my comic book collection? Oh god—had I told her that I had like seventy blank CDs all filled with bootleg concerts by The Dave Matthews Band!? That must have been it.

The Lesson: It's not always about you.

People have a tendency to see themselves as the protagonist in all of life's stories but that simply isn't true. Sometimes you're just playing a supporting role in someone else's tale. This was one of those times.

My six days with Mary weren't about me—not really. She raised her hand in class. She told me to kiss her. She told me to go out with her. She initiated all of our time together. Then she broke up with me telling me that things were going too fast and she needed some time to regroup.

I don't think I was ever all that important to Mary. She was a strong woman who was attracted to me and wanted to see what all of that 'boy stuff' was like so I was the obvious target. Once things became a little too real she needed to step back and figure out what she was going to do about it. I was collateral damage.

In Magic finance it is always important to broaden your viewpoint. When you think of yourself as the hero in your own story it's easy to get swayed by your own experiences and biases. If you spend an evening losing to Hero of Bladehold chances are you're going to overvalue the card in your mind. It's just human nature; the card was great against you so therefore it is probably undervalued right? Well maybe. Maybe it was just a fluke. Or you were playing a really bad matchup. Or you just didn't draw your removal at the right time.

It's also important to realize that a new market has officially started to affect the price of Magic cards in a major way: pure speculators. I'm not going to pass judgment on them for now though I may talk more about this in a future article. The point is that you now have to consider hype and speculation as a real effect when analyzing the market for a card. Enough people are doing it that it has a massive impact on card prices.

Consider Wolfir Silverheart. He was sitting between $1 and $2 before the latest Pro Tour but the coverage from that morning was showcasing just how powerful the card was. Nearly every deck in the room was designed to take advantage of it or beat it.

Naturally there was a run on Wolfir Silverhearts everywhere. A week later the price sits at $8 on StarCityGames.com—but it's sold out. It's difficult to find them anywhere for under $10 retail.

This would make sense…if the pros had been playing Standard. But they were playing Block a format for which there is literally no demand on the local level.

Based on pure playability the card should be in the $4-$5 range. It's a very good monster and I still think that is where the price will settle. But speculators went mad buying them up and the card rocketed past $10 by noon. It still hasn't come down.

You can have a spot-on analysis of the format but sometimes it isn't about you. Sometimes a couple of guys with a lot of money create a swirling maelstrom of demand and stores have to raise the price of a card to compensate. With Wolfir Silverheart the age of rampant speculation in Magic has officially arrived.

Erin

It didn't take much to start a club in my high school. All you needed were a couple of signatures and you were good to go.

Junior year I decided I wanted to start a Magic: The Gathering club. After asking around I learned that Erin—a quiet girl I who I didn't know all that well—had been thinking of starting one too. We decided to partner up in order to get more signatures.

It worked. We're both in the yearbook that year standing next to each other on the club page holding Ornithopters.

At the time I was dating someone else (a wild and horrible story for the next time I do an article like this) so I didn't think about Erin in a romantic way. We played Magic together a lot that year and she won our first-ever tournament but we didn't hang out much otherwise. Even though we had started the club together there were a lot of bigger personalities we orbited that commanded everyone's attention. They were all a year older than us though and by the start of our senior year she was one of my only friends that hadn't graduated. We started spending more and more time together and by the end of February we were going out.

Our relationship flourished over the following months. We both decided to go to college in Boston albeit at different schools and we were together constantly. Being with her was easy and fun; she was never boring and our life was never a chore. I started thinking she was 'the one' and most of our friends did too. I idly assumed we would get married after college and start a life together.

Her brain chemistry had different plans.

Erin suffered from a variety of psychiatric conditions that made life a constant struggle. She was taking medication for depression and bipolar disorder when I met her but during our first year and a half together she was both happy and stable.

Unfortunately these things can change overnight. Her medicine stopped working and it took her doctors several years to find a new cocktail that would restabilize her mood. During the interim bipolarity made her life a living hell. In her depressed states she was a total mess. In her manic states things were even worse: she would try to sabotage her happiness and our relationship.

I thought I could deal with it. I thought I was a stable enough person to sail above the waves and not get sucked into her vortex of unstable emotion. "It's not really her" I tried to tell myself. "She doesn't know what she's doing right now. She's sick. You're mad at her disease not her."

But I couldn't do it. I hadn't fully internalized the lesson I learned from Caroline (don't idealize people) or the lesson I learned from Mary (it's not always about you). My paladin complex was also in full swing and I was operating under the assumption that I could somehow 'save' her as though she was a frail damsel that needed to be shielded from dragon fire. I hadn't yet realized that the battle she was waging was far bigger than me and her bravery far greater than mine.

I refused to let go of anything. She needed space but I insisted we talk through her transgressions and try to find a way forward. I asked her to explain herself when she was doing things that were completely illogical. Even when she broke up with me I spent the next six months trying to get her back. And I did—but only for a few months until things ended even worse. I destroyed myself for this girl and that year was absolute hell.

The Lesson: Know when to let go.

At the time I thought the lesson I would learn from Erin would be different. I believed that my problem was simply a weak will. Perhaps if I had stayed with her and simply let her disease run its course until her mood restabilized things wouldn't have ended so poorly.

That's fiction too.

My favorite quote about love is from the character Spike in an old episode of Buffy the Vampire Slayer. When Spike saw Buffy and Angel pretending that their tragic past was behind them he gave them the following bit of wisdom:

"You're not friends. You'll never be friends. You'll be in love 'til it kills you both. You'll fight and you'll shag and you'll hate each other 'til it makes you quiver but you'll never be friends. Real love isn't brains children. It's blood. It's blood screaming inside you to work its will. I may be love's b**** but at least I'm man enough to admit it."

The truth is that I never could have been the person she needed me to be in those dark moments. I loved her too much and being there always would have destroyed me no matter how strong my will

The only thing I could have done would have been to leave—to allow her to work things out with her doctors and to reenter her life in some capacity when she was ready to see me again. Instead I stayed. I turned my world upside-down trying to make sense of insanity. Trying to realize how something so wonderful could become so corrupt.

Believe it or not though this story has a happy ending. Erin did eventually find a medicinal cocktail that allows her to live a happy stable awesome life.

And six years later I can tell you that Spike's quote isn't entirely true. Time has reshaped us our lives evolving in a hundred different ways that have brought us worlds away from the end of our failed relationship. We are friends now the awkwardness long gone. She's currently engaged to one of the best people I know and their life together is fantastic. I couldn't be happier for her.

I just wish I had let go sooner and spared us both from so many nights filled with anguish and betrayal.

It's hard to let go in Magic finance too. Being objective is easy when you're not actually faced with making tough decisions. This is the same fallacy that makes people think they'd be great at running a Major League Baseball team or that they'd be able to destroy the competition if they were ever allowed to be on Jeopardy. Once you're actually sitting in the drivers' seat decision-making gets very difficult.

Just like in a relationship people have the biggest problem letting go of financial subjectivity in times of extreme volatility. When a card price is shooting into the stratosphere you often have a very small window to sell at full value. While the price may take a few days to 'officially' drop there is a point when demand for a card at its high value suddenly dries up. When you reach this point your window to cash out at maximum has officially closed.

Things are even worse when a card is on the way down. In the past I've talked about the sunk cost fallacy which is a human tendency for people to fixate on price points in the past in a futile attempt to recoup what they believe is lost value. Instead of looking at the road ahead and judging whether to sell based on what might come next they look at the old price and do what they can to try and get their investment back to that number. In many cases they hang on far too long and end up with nothing.

The best time to sell then is at some point on the way up. But when? How do you know when the time is right? What if you sell too early and miss out on the card's true ceiling?

When investing in a card it's important to understand how stable your investment is and how volatile it is likely to get. Wasteland for example is a card with low volatility. The only time that card ever starts making a massive climb or dive is when the entire Legacy format is going through massive upheaval. There is never a need to panic sell Wasteland.

When a volatile card 'breaks out' like Wolfir Silverheart did last weekend there are usually a few stages:

- Online rumblings usually on Twitter of a card on the rise. The financial experts and savvy grinders tend to be the first ones in.

- A run on the reputable stores and eBay. This usually takes 2-3 hours.

- A restock on StarCityGames.com and other online retailers. Sometimes the price is just raised a couple bucks but remains out of stock.

- The next morning the price is up everywhere but the card is entirely out of stock. This is when you see a $1 card up to $10 but you can't find a copy anywhere.

This is generally the best time to sell. Usually though you'll have to wait about a week for your orders to come in so you can't take advantage of the high price unless you have stock on hand. In 3-5 days once the cards from the retailers have been delivered to the speculators they'll start to flood the market in an attempt to unload. At this point the card drops back down to whatever price it 'should' be since player demand begins to overtake speculation demand.

When the price first starts to drop again your natural inclination will be to hang on for dear life and try to ride it back up again. This is almost always wrong (unless the card is a true 5 out of 5 Jace the Mind Sculptor or Stoneforge Mystic); the price will come down from this initial high. Sell while you can.

Emma

My friends warned me not to go out with Emma.

I was still reeling from the Erin debacle and I had finally gotten my self-esteem up to the point where I wasn't curled up on my best friend's carpet most nights shouting about the tyranny of the heart while we watched South Park. The timing was also horrible; it was only two weeks before college summer break and I was due to spend the first semester of my senior year living in LA and interning at a production company. My life was about to enter a period of great physical flux and the last thing I needed was an emotional commitment that I was in no way prepared to make.

I ignored them. We went on our first date during the last week of classes and I brought ice cream to her dorm on the first night of finals. As luck would have it our parents' houses were only about an hour apart so I spent a good portion of my summer driving my fifteen-year-old Cadillac up 495 from Harvard to Lowell taking Route 3 to Burlington and then bombing up 128 to Gloucester. When I moved to LA we decided to keep the relationship as a long distance thing even though I knew there was a very real chance that it wasn't going to pan out.

The Lesson: Nobody knows anything.

The great screenwriter William Goldman once said that the number one rule in Hollywood is that nobody knows anything. The same is true in love.

Just last month Emma and I toasted to five years together. We live together in LA now and couldn't be happier—all because I started a relationship that by all odds should have failed.

At some point you have to throw logic out the window and take a leap of faith. In finance make sure that you never risk more than you can afford to lose. In love it is crucial that you don't hurt the friends and family you rely on. If you're anything like me you'll have your share of failures but that's perfectly normal and perfectly healthy.

It just makes victory taste that much sweeter.

Until next time –

– Chas Andres