I’ve been in the dating sh*tter a few times. It’s cool. 

If you have too, solidarity, my friend! Dating can be rough. Especially if you’re looking for something real, and it really doesn’t work out.

That said, dating has its perks. Each person you meet will teach you something new, if you let them. What are their beliefs? How do they see the world? What’s it like working in their current profession? Why are they passionate about xyz?

Some things you learn will be illuminating. They may even influence your own life path. Other times, you’ll learn tough life lessons that simply make you stronger.

In any case, dating is an opportunity. Not only to learn about others, but also to learn about yourself.

The more you know yourself, the more you’ll know what you want in a partner. And that knowledge is worth its weight in gold.

But wouldn’t it be nice if we could avoid dating fails altogether? 

A worthy endeavor. And I’m not sure if it’s possible. But my promise to you? The lessons I’ve learned via my own dating fails will give you a fair shot. Check ’em out: 

1. That guy who brought PBRs to a date

If you’re into PBRs, rock it. We all have our tastes. (My sister actually loves them, and her date scored major points by bringing PBRs to their date.)

BUT — PBRs did not save the first online date I went on.

He had one profile photo that did not look like him at all. His profile said he was a lawyer.

On our date, he droned on to me, a law student, about how law was a horrible career choice. He admitted he wasn’t a lawyer, as he didn’t pass the bar exam.

He chose the Marriott lobby bar (he was not staying at the Marriott) for our date. He didn’t order anything. He then pulled out PBRs from his briefcase and started chugging them.

He asked if I and my Marriott beer could join him in the hallway, so he could drink more PBRs. I avoided other peoples’ stares and crawled into my metaphorical shell.

At the end, he lunged at me without warning, forced his lips (slobber?) onto mine, and said he had a great time. I told him I’d “see him later.”

Sigh. Such is life.

man drinking beer

HOW YOU CAN AVOID THIS:

 1. Do not rely on a single photo on someone’s dating profile, if you’d like to know what they look like beforehand. (Especially if it’s covered in shadow — my bad.)

 2. If you have a good date idea, suggest it! It’s awesome when your date already knows a spot, but it’s okay to choose a place, too. (Especially if the alternative is a hotel lobby.)

 3. Don’t be afraid to speak up on a date. We all want to keep the peace, but if someone says something offensive, it’s okay to say you’re offended! We all have our boundaries.

 4. Say no to hallways, alleys, etc. on a first date. (Or any date? Idk. Do you.)

 5. Be honest at the end of a date. Don’t say “see you later” if you mean “see you never.”

Does it take a little more effort? Yes. Is it awkward to reveal you’re not interested? It can be. But being honest saves them from waiting and wishing.

If you’ve ever been on the other side of this, you know it’s the worst. Spare someone from that, and hope that kindness is returned to you one day (if you don’t meet the love of your life first!). 

2. That guy who told me to “not be such a fan”

This is a short story. Girl meets guy, guy is great, and girl falls too hard too fast. Before she really knows who guy is.

At least, I think that’s how he saw it.

He was driving us to my place, and I complimented him in some way. Can’t remember how — but it was something simple. His eyes, his intellect, whatever.

But I’ll always remember the moment he turned to me and said, “Don’t be such a fan.” 

It was one of those simple moments that most would forget. But it got me thinking.

Is this why people sometimes hide their feelings? Play hard to get? Play the “cool” person who’s just looking for whatever?

Because they don’t want to be “such a fan?”

Bachelor #I-lost-count and I had a good night. We talked about life and philosophy as we sipped Manhattans.

woman covering her face with a fan

Then he went home, and I never saw him again. I never learned who, really, he was. It’s all good. Anyway, here’s how you can try to avoid this scenario.

HOW YOU CAN AVOID THIS:

1. Don’t date people who don’t want fans. I’m currently in a beautiful relationship, and I am my boyfriend’s biggest fan. He is mine. It’s another way of saying we love each other. That said, I get you don’t want “too much too soon” in dating. So:

2. Remember you don’t know your date. You’re getting to know them. It’s easy to get caught up in the romance and what could be. They’re attractive, respectful, and have a good career?!

But it takes time to know someone. The seemingly best person could turn out to be a horrible match. And someone who doesn’t catch your eye at first could become your life partner. Life is weird and awesome!

3. Remember your date is evaluating you, too. Ask yourself: are they a fan? Because for me, I’m not down to be a fan of someone who isn’t my fan! (Jk – kind of. I’m just saying it’s best when appreciation goes both ways.)

4. Come from a place of confidence. People can smell it. If you compliment someone from a place of confidence, they’ll feel flattered. If you compliment someone from a place of insecurity, they may feel uncomfortable.

For example, let’s say you value physical health, but you’ve been skipping the gym lately. If you say to someone, “You’re so fit! I wish I could look like that. I just can’t keep up a consistent workout routine . . . I’m the worst,” you’re placing them on a pedestal.

And while self-deprecation can be used humorously at times, it’s probably best left out of this scenario.

If you instead say, “I love that you make working out a priority! It’s important to me, too,” you’re complimenting that person from a place of confidence.

While you haven’t been to the gym lately, you still value physical health. And highlighting the latter fact displays more confidence and positivity.

In any case, we should all strive to cultivate confidence for ourselves, before others. It’s just that confidence helps in dating, too. 🙂 

3. That guy who said I was “his person” and then no-showed to Valentine’s Day dinner

Okay. So this was THEE WEIRDEST. 

I meet this guy, and he’s a realtor and model who shows up on local billboards sometimes. He’s got pretty eyes, an infectious laugh, and a sense of adventure. He sings songs on his guitar.

Fast forward — we’re relaxing on the couch, those pretty eyes look into mine, and he says, “I think you’re my person.”

I’m like, woah. But also kind of pleased. Could this be the guy?

I certainly felt things inside me, but I needed more time for those things to evolve. And he met my sister and some friends, so there was that.

So when he invited me to dinner on Valentine’s Day, I said yes. Thing is, he never showed.

I ended up joining a group of girl friends out for dinner. I ate a big burger, and yes, I got a little teary eyed. They helped me through it. Thank god for friends.

wine being poured into a glass

HOW YOU CAN AVOID THIS:

1. Take things slow. If the person in your life is truly the one, you have the rest of your lives together. What’s the rush? Let feelings evolve and deepen on both sides, as naturally as possible. If you’re truly a match, the right things will fall into place.

2. Remember it’s easier to say than to act. People can say all kinds of things, but pay attention: do their actions measure up?

No-showing on Valentine’s Day certainly did not. But sometimes, the lack of action will be more subtle. Do give people the benefit of the doubt, but don’t settle for less than you deserve.

3. Consider holding off on introducing friends or family to the person you’re dating early on, if this is a big step for you. (For my sister and I, we’re pretty free-flowing when it comes to intros, but everyone is different.)

If things don’t work out, not having introduced your person to others in your life could help make the break easier.

4. Never say yes to Valentine’s Day dinner early on. (Jk — a solid Valentine’s Day dinner is always worth the risk, in my book!)

It’s Just a Bunch of Land Mines. You’ve Got This.

Okay. So that was a lot. And you’re probably thinking, oh sh**, there’s a lot to try to avoid in dating.

And you would be right. 

Dating is like crossing a field with a bunch of land mines. Your happily ever after is waiting on the other side, and you’ve just got to cross safely. It seems so easy and simple, but it’s not always.

You could get lucky and encounter no troubles along the way, or you could get some bumps and bruises. But in any case — you can come out of it stronger and happier than ever. It’s all about perspective.

You just have to go for it.

Be smart, but be hopeful. Be patient, but be determined.

And, most of all, be bold.

Xoxo,

Sam

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