Lessons Learned From Failed Loves

I’m a 33-year-old man.

I’m also single.

That realistically means every single relationship I’ve ever had has ended in failure.

To be honest, when I look at it like that, it’s kind of depressing.

But I like to think of myself as the Thomas Edison of relationships.

Sure, I’ll fail on the first 10,000 attempts, but gosh darn it, relationship 10,001 is going to be the bee’s knees!

I’ve also been married once.

For a whopping six months.

You see, I went to film school, so I wanted to get that Hollywood marriage length under my belt before anything else.

I haven’t come close to having a serious relationship since.

You know, the “I’m taking this one home to mom” serious.

Although I have told my mom about a few here and there.

While I could dive into the current state of my relationship desert, I find it much more beneficial to look at the lessons I’ve learned from failed loves.

Age Is Just A Number…Until It’s Not

My first little innocent crush came in the first grade. Girl named Danielle.I don’t remember much of it, to be honest.

But what I do remember is that at the ripe old age of six, I had convinced myself girls liked candy and flowers.

My dad wasn’t exactly the gift giving type, so honestly, I’m not totally sure where I learned the magic of sugar and pretty colors. Probably from the daytime soap operas my mom would watch.

Anyway, I was invited to her birthday party. So I showed up with a single rose and a Nestle Crunch candy bar (sidebar, Nestle Crunch candy bars are heavily underrated).

I don’t remember how any of the party went. Other than it was a “Wild West” themed party, so I delivered the flower and chocolate bar in cowboy boots, cap blasting six-shooter slung over my hip (and let’s face it, probably dragging down past my knees), and a vest.

Needless to say, I don’t think we ever had another grade school class together after that. And in the days pre-cell phones and social media, there wasn’t anything more of a relationship death warrant than that.

At that time, age was just a number. It was the exchange of candy and talking with someone who had fewer cooties than her friends.

Flash forward 27 years and age is so much more than just a number.

I’ve found the vast majority of dates I go on, when I decide to go on them, are with women younger than me.

They say it’s because they like a more “mature” guy.

But they only think that because they haven’t seen my Star Wars LEGOS yet.

Every time such a date comes about I always convince it will be different from the last one.

But the reality is, it’s not.

Being 33 and going on a date with someone who’s 21 might sound like swell math for many guys out there, but our lives are in two completely different places for it to ever be compatible.

Hell, The Simpsons had been on television for nine years before she was even born (yes, I do compare someone’s age to how long The Simpsons had been on TV prior to their birth…which again probably contradicts that whole “mature guy” notion).

Needless to say, age is just a number in some cases, but in this stage of my life, it’s much more than that.

There Is Such a Thing As Going Overboard With Gifts

My dad wasn’t great at giving my mom gifts.

Well, let me clarify that a bit.

My dad wasn’t great at putting much thought into his gifts. Every Christmas he’d give her a general gift certificate to the mall. Which she’d more than likely end up spending on my sisters and me.

To not throw complete shade on my dad, my mother is that one person in the family who’s impossible to shop for, but still.

Early on, and I mean really early on, I vowed I’d never been like that. I’d do what I could to put as much thought into the gift.

In the back of my brain, going over the top with a gift always seems like a good idea. In reality, it isn’t.

Because the bigger the gesture, the bigger the letdown. It can also terrify the person because they don’t know how to react to it.

The first girl I’d say I was head over heels with, back when I was 19, I planned this big birthday event for. I rented out an ice skating rink (because she loved it as a kid but had to stop because her twin-brother hated it), followed by courtside tickets to a Detroit Pistons game (because she was a super fan).

I even had them put up a Happy Birthday message on the scoreboard.

I get super excited and pumped when I’m planning something like that. There’s just a great feeling of picking out the perfect gift for someone. Which I thought I did.

Anyway, I had all of this as a surprise. Didn’t tell her what was happening. Just to have the day cleared. Annnnnnnnd the night before when I called her she told me she went back to her ex-boyfriend.

CRASH!

Oh, that sound was my heart slipping past vital organs and smashing at my feet.

So that sucked.

That one might have just been bad luck.

Maybe.

But it’s been a bit of a recurring thread that’s continued on for basically the history of those failed relationships.

I won’t get into the others. Let’s just say there’s plenty more, and some are much more elaborate.And yet I’ll probably never stop doing it. I like it. Makes me happy.

But what I’ve learned is to just not expect any kind of grand reveal. Because grand reveals are for car commercials and The Price is Right.

Sometimes it works. Most of the time it doesn’t.

But that’s life in general, isn’t it?

Can’t Buy Me Love

So that six-month marriage thing.

That was something.

Long story short caught her doing things (other guys) she shouldn’t have been doing maybe two weeks before the wedding.

Why I didn’t cancel everything is something I’ve thought about more than a few times.

And yes, I did seriously consider being the guy on those YouTube videos who pretend to go through the entire ceremony, only to call her out at the vows portion.

But I didn’t.

And I still went through with it.

Why?

Well beyond being an idiot, it’s because I was paying for the entire damn thing. Which included flying a family friend up from Jamaica to be the minister (you want to feel better about life, have someone with a Caribbean accent talk to you for an hour).

I also had friends flying in from Florida and California and New York. Didn’t want them to be stuck with expensive flights they couldn’t cancel.

Probably the most important lesson I’ve learned about relationships to this date is if money is playing any part in keeping you around, run as fast and as far away as you can. Because it’s not going to end well.

I know plenty of people who are in current relationships because of the cash. Because they are showered in presents and jewelry and boob jobs. The thing is, there will always be other people with more money.

There won’t always be other people who can be there mentally and emotionally.

It’s About Knowing What’s Best For You (and Fair For Them)

Few years back I was seeing this girl.I wouldn’t say full blow relationship yet, but teetering on the edge. Every single guy friend I had wondered how in the world I was able to swing it.

Kids on the street might say I out kicked my coverage (a term I’ve never been a huge fan of because usually when a punter outkicks his coverage there’s a greater chance of a big kick return….but that’s beside the point).

Yet it didn’t work. And I had to walk away.

Because I was so engrossed with work that it wasn’t fair to her.

I was spending most of my free time on a screenplay. Basically non-paying work that I did on top of regular work.

Because that’s what I want to do when I “grow up.”

It, like most of the other screenplays I’ve done up, has been received well at competitions, festivals, and that kind of things.

But as many of you know, there’s a massive difference between doing well in a festival and signing an agent.

Trying to track down an agent is itself a full-time job.

She asked me what would happen if I couldn’t sell that story.

I told her I’d keep trying.

And I’d write another one.

And another one.

And another one.

Until it did sell and it did work.

Most people don’t understand that. They think its crazy or dumb or a waste of time.

Maybe it is.

Yet maybe it isn’t.

It’s something most creative minded people understand and what more structured minds don’t. Attempting to explain this philosophy to an accountant leads to nowhere.

And so I decided it would be best to almost cut myself away from most relationships because the other side would likely never understand my need to devote so much time into it.

Lessons I’m Trying Not To Repeat

So many lessons.

I’m trying to keep hold of them and to learn from them, so I don’t make the same mistakes twice.

Because if I am the Edison of dating, I still have like 9,870 lessons to learn, and repeating them will delay finally discovering the one love that works.