The Playbook For The Modern Man

High Level Dating Mistakes Smart Guys Make

Cocksure as a Mexican Matador? This one’s for you.

You roll up in your Carrera, Persols askew, podcast bubbling and Ralph Lauren ‘popping’. You nab the last park, and stroll in, one minute to spare, feeling cocksure as a Mexican Matador.

You order an extra hot Macchiato and sidle up to your date. You chat, get to know each other, and even have a couple of mutual interests. Coffee! Books! Music! Surely this was destined to be.

Fast forward two weeks and your romance has stalled, you’re both talking to other people, and neither of you quite know how to end things.

But you’re smart. What the hell went wrong? This guide to ‘the dating mistakes smart dudes make’ should help you understand why.

Not initiating

Think your Porsche speaks louder than words? Think again. This is a pet annoyance, which a trending thread, posted nine days ago into Reddit’s r/dating community, called, “Stop expecting people to take hints! And don’t feel bad if you don’t pick up on them,” attests is a real pain in the hot pants.

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“This is a major peeve in dating and relationships and life in general, but especially with someone you’ve just met/are getting to know. We are adults and would probably be much better off confronting things and just stating what we think is obvious (but may actually not be obvious to the other party). Most of us miss social cues at some point or another and the nerves and excitement of dating makes some of us completely blind.”

Killing chemistry

There are two reasons to postpone a date. 1. It’s a power move. 2. You can’t make it.

If it’s the first, you’re shooting yourself in the foot. Think of your fling like a clay pigeon. Not the suavest analogy but bear with us. From the moment you match, your possible ‘bed frame busting’ relationship is hurtling away.

The more time goes by, the less the chance you’ll get together, and the more things will start to feel stale.

Trying to rehabilitate a ‘bad girl’

Every women’s website ever has an article on ‘how to rehabilitate a bad boy’ (or why you shouldn’t do it). Well, the shoe’s on the other food now and let us turn to Glamour to understand why, “Knowing when to cut your losses and move on leaves you available and baggage-free when the right [person] comes along.”

The solution? Let them take you for a ride, enjoy every it, and keep your expectations in check.

Rejecting anyone who isn’t a carbon copy of you

Because if we all liked Trigonometry, cryptocurrencies and craft beer, the world would be one giant set of nails-on-a-chalkboard. Also, opposites make good teams, even if they don’t always attract.

Playing it too cool

While less sophisticated dudes fall prey to talking about their ex or wiping their mits on the table cloth, you are one sophisticated MF. You lounge in your seat and deliberating like a French Professor from the school of Fug Youse literature.

You also speak only in rhyme, and preface everything with a scoff, saying things like “it just comes down to a case by case basis.” Please reconsider this behaviour.

Running from red flags

Think you’ve got this whole thing figured? Guess what? Red flags build character. And if you’re hitting the apps with anything other than a Chris Hemsworth rig and James Corden personality, you’re going to need it.

Having breakfast phobia

Just a heads up: having breakfast together doesn’t mean you’re getting married. And a French Press is the key to anyone’s heart.

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  • Doug Keating

    Good article. I would be careful ignoring red flags. They are there for a reason.

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