Let’s talk about one of the scariest things around dating: how to text a woman you’re interested in.

I can’t tell you how many times I’ve worried that I’m texting her too little and she’s going to forget about me, or I’m texting her too often and she’s going to think I’m clingy, or even that I’m texting her something that gets taken the wrong way and now she’s super offended at an innocent comment I made.

And the worst of all is when you text her and she doesn’t respond…for…several hours. When that happens, all I can think about is basically,

• “Did she see my text? Maybe she didn’t see it yet.”
• “Is she busy? What is she doing?”
• “Why hasn’t she responded yet? OMG she probably hates me.”

Continue reading How to text her – including scripts and examples →

From the first time I saw her face, I knew I’d love her until the day I die.

I can still picture it clearly today. All the other boys in my Middle School were fawning over that one redhead who looked like Mary Jane from Spider-Man (you know…the Tobey Maguire one).

On the other hand, I happened to crush on my classmate in English class who came in every day wearing a ridiculously cute Mickey Mouse shirt and headband. She was the first person I ever had feelings for.

I’d like to tell you that she never even knew I existed. That’s what I really want to write right now because it would hurt less to whitewash the story and remember it a different way than how it really happened. But that wouldn’t be true to myself.

What really happened is that some time later, one of her friends secretly came up to me and told me “You know, Chloe used to have a crush on you for like, forever.”

That hurts because it’s one thing if I never even had a chance. It’s another thing to know that the first woman I ever found myself crushing on actually liked me back and I just let that slip through my fingers!

Looking back, it’s a mistake I’d made many times throughout my dating life. Whenever I found myself romantically interested in someone, I’d fail to unambiguously convey my romantic interest. That’s the key. If you too indirect and treat women that you’re interested in as friends like I did, then you can’t be surprised when you only end up being friends and nothing more.

Here’s an example to show what I mean:

• Morning coffee or lunch with a coworker? Not romantic because people do this all the time professionally.
• Inviting a coworker to a group activity with you? That’s ambiguously romantic because friends also do this platonically, and professionals commonly do this for networking purposes.
• Asking a coworker to watch a movie and have dinner with you on a Friday night? That’s unambiguously romantic because you’ve set up a series of 1-on-1 activities just for the two of you and you’re meeting her on a night when you can stay out late and not have to worry about going to work the next day.

The key is to unambiguously convey romantic interest. If you treat her platonically then of course your relationship will be nothing but platonic. But if you ask her out 1-on-1 to an activity at a specific time and place, then she’ll know that you’re interested in her. And maybe…just maybe…she’ll be interested in you back.

I’ve loved a lot of women throughout my life. I have two competing memories of the first woman I ever loved, and I wish I could remember it the less painful way but that just tastes like a lie. I can tell you with a straight face that most of the other women I crushed on probably never even knew I existed. Maybe I’m whitewashing those memories as well when I say that. But I honestly don’t know and that allows me to honestly remember it that way.

Ever had an Uber ride was off-the-rails crazy?

I have. It had neon lights, a freaking disco ball, and some sort of weird glasses on the driver’s face that, in hindsight, I sure hope to God wasn’t covering up a lack of sobriety.

At the end of the ride, the driver turned to me and asked “Hey! Did you know I’m also a rapper?’

“No. Really!?” I reply with feigned surprise. Given all the wacky stuff in this guy’s car, the fact that this guy creates rap music was perhaps the least shocking thing that night.

“Yeah! You should check out my channel,” he says and gives me the name of his channel.

“Will do. Thanks!” I reply, stumbling out of this strange car.

(In the words of Stephen Colbert, “Guess which state this happened in? Never mind, it’s Florida.”)

Well, I have to confess that I never did check out that guy’s rap channel. I wanted to, I swear! But as soon as I got to my destination, I went about the rest of my night and the events of that Uber ride fell out of my brain about 30 seconds after I stepped out of the car. I wish I could tell you what it was called so you could check it out for yourself but I’ve totally forgotten what the name of that guy’s channel was.

When that Uber-driver-slash-rapper was telling me about his channel, he made one fatal mistake. Can you guess what it is?

His mistake was that he left the ball in my court.

Of course, I wanted to check out his channel! But once I stepped out of the car, about a thousand other things started vying for my attention and I just totally forgot about it. He could have prompted me to pull up his channel and subscribe to it while I was still in the car. Or, at the very least, he could have written the name of his channel down on a piece of paper and handed it to me.

But he didn’t. He committed what Ramit Sethi calls a “failure of the last mile” and left me to do it on my own. This cost him not just one potential follower (myself), but many potential followers since I could have recommended you the name of his channel if I thought it was any good.

It’s easy to point out how he screwed up by leaving the ball in my court.

How many of us are doing the same thing when it comes to women?

Continue reading Don’t leave the ball in her court →

Once upon a time, I used to look like this:

That was in high school, back when I was too dumb to realize how dumb I looked. I mean, jeez! Did I seriously go outside looking like this??

Give me a second to bury my face in my hands until I get that picture out of my head…

…

…okay, I’m back.

Here’s what I look like now:

Hey, that’s a lot better!

So, how do you go from having hair that looks like a helmet, to looking presentable in public? I have absolutely zero fashion sense and, honestly, I just have someone do it for me. It’s easy! Just find a good hair salon or barbershop near you and let them know you’d like their professional judgment in getting a haircut.

This is the important part: if you’re like me and don’t know what makes a good haircut, just let them cut it for you! Don’t tell them how you would like your hair done if you have no idea what looks good on you. Leave it to the professionals.

Of course, it helps if you check the reviews beforehand and make sure it’s a good place. It also helps if you research the barbers and pick a good one. Personally, I have the owner of my local hair salon do my hair because I know he’s skilled. It’s easy to tell who the owner is because his own name is in the name of the salon.

After getting a haircut, how do you know if it looks good? By the way your friends react. Do they say things such as, “Nice haircut! It suits you.” Or are they like “Hey…you got a haircut.” If your haircut turned out less-than-stellar, try getting a different barber or going to a different salon altogether.

Getting a professional haircut is a quick and simple way that I improved my appearance (and boosted my confidence) with little to no effort!

Let’s talk about where to go on a first date. You want to leave a good first impression, and the venue you choose sets the stage for the rest of the evening. I’m going to share a few guidelines I always used whenever I was trying to decide where to take her on a first date, then I’m going to give you my personal favorite places to go on a date.

Continue reading The best places to take her on a first date →

You ever have a time where you’re lying in bed, trying to fall asleep, and then your brain suddenly decides to be a jerk and replay all the embarrassing things you’ve ever done in uncomfortably vivid detail? Turns out there’s a name for that. It’s called “Fridge Horror”. This happens when you experience something horrifying but it doesn’t register in your brain until much later, such as when you’re rummaging through your fridge the next day trying to grab a midnight snack. For example…

…this was my face when I watched Star Wars Episode 6: Return of the Jedi for the first time, and…

…this was my face when it dawned on me that the cute and cuddly Ewoks probably ate all the fallen Stormtroopers after the film ended.

I still kick myself over this one mistake I made a long time ago. Not as hard as I used to since I’m married now, mind you, but still on occasion when I’m trying to sleep and my brain decides to remind me of all the dumb things I’ve done in the past so I wake up at like 2 in the morning and my wife just looks at me weird.

My pain is your gain. I made these mistakes so you don’t have to. Enjoy!

Continue reading What really happened when I followed the “Three Days” rule →

Back when I was in college, I always stressed out about dating. I believed that I absolutely needed to have a girlfriend before Christmas because the holidays are the time of year that you spend with a woman you love. Same thing with New Year’s. And don’t get me started on Valentine’s Day.

None of that helped, though. It just made dating much more stressful for me. If I could go back in time and give some advice to my younger self, I’d tell myself not to take it so seriously.

Dating is supposed to be fun. If you’re finding the whole thing to be a little bit too stressful, maybe it’s time to take a little break from it. There are no deadlines that you need to hit when it comes to finding love. Take some time and go work on yourself. Read a book. Watch your favorite TV. Work on your hobbies. Meet some new people.

Go enjoy yourself! When you’re living a life that you enjoy, dating becomes a lot less stressful and a lot more fun. I promise that the women of this world will still be here when you are ready.

Getting a first date can be hard. Getting that second date can be harder.

I’ve had a lot of first dates with women I met online that have not led to second dates. I’ve had women tell me that they didn’t feel a romantic connection. I’ve had women tell me that they’d rather be friends. I’ve had women agree to go on a second date and then later cancel on our plans.

And, occasionally, I’ve had women just stop texting me altogether.

When you meeting her from the internet for the first time, how do you have a great first date with her so that she’ll want to have a second date with you?

Continue reading How to have a great first date with women you meet online →