Cool Guy Summer Dating Edit: Style & Image

Okay, I do have some very light expectations for you. I simply expect that you read each Substack I post from beginning to end, which means you already knew the Summer Dating Edit was coming, right? If you didn’t, that’s your sign to get caught up here. Am I asking for too much!?

Now let’s get down to business. So I have a friend. One of my hottest girlfriends, and she went on a date with this great guy recently. He’s an art dealer, very put together, amazing style. He was checking every box.

They met at this cool restaurant in Venice on a Friday night. She loves this place. She had her outfit all picked out, scheduled her Uber, and updated the group chat on the whole play-by-play. Everyone was highly invested.

So she gets to the date and from the second they sat down, he revealed somewhat of a plot twist: he had other plans. It went something like, “I have to get out of here around 8PM, my buddy planned a dinner party later.”

Uhhhhhhh. As you can imagine, this came as a shock. Now, they had matched on Hinge, they messaged for a few days, they added each other on Instagram. Enough banter and rapport was established for her to assume this date was the dinner.

And if we backtrack, that’s where it was a little vague. When he set up the date, he never said “dinner,” but given that it was a Friday night, she assumed.

“Let’s meet at Market around 6:30” were his exact words, I believe.

As someone who works exclusively with men on their dating lives, this date setup moves us into some gray area. I like when men are very direct with making the plan. They make the reservation, set the location, choose the time, send a confirmation text, etc. There’s a whole protocol.

But this one was purposefully vague, which I don’t love. “Let’s meet for dinner?” Love that. “Let’s get drinks at 7PM.” Sure. “I want to see you. How’s dinner / drinks at Market?” Brilliant.

But this guy chose a restaurant (not a bar), booked a prime dinner hour, and booked her on a Friday, one of the most desirable nights of the week.

So from the beginning, this made her feel like their date wasn’t his main event. In her eyes, he was using it like a pre-game for something else. And look, I would give this guy a little grace if he had mentioned it from the beginning, if he was setting the plan with a genuinely busy schedule and really wanted to see her anyway.

There are a few variations where the double-booked night could slide, but this particular case didn’t qualify.

So from that point forward, she felt incredibly awkward on the date. They ordered drinks and some light bites and of course the service took forever. Of course the restaurant was extremely busy. Of course it was loud and they could hardly hear each other.

And to make matters worse, he was stressing about the time the entire date. Sometimes a 1.5 hour date feels like enough time, but other times, when you’re at one of the most popular restaurants on a prime night, it takes 15 minutes just to get seated.

So the night ended up being a disaster. They never really hit a good stride in their conversation, and not only did she not want to go out with him again, she was ready to swear off dating at that point.

This is what happens for girls, and it’s highly important you pay attention. By the time you’re going on a first date with your dream girl, she has been on so many let-down dates like this one that, by the time you show up, you’re not just being compared to some idealized version of a boyfriend.

You’re being compared to the art dealer. To the guy before him who cancelled twice and rescheduled a third time like it was nothing. To the one who couldn’t recover when the conversation went quiet and just let it die there. She’s not grading you on a scale of 1 to 10.

She’s grading you on a curve against a rotating cast of guys who couldn’t get the basics right, and most of you have no idea how low that bar actually is. That’s not a compliment to them. That’s a very strategic opening for you.

So here’s what we’re doing with that opening. Inside the Cool Guy Dating Edit, I’m breaking down the exact 3 variables that separate the guy she deletes the number of from the guy she’s telling her friends about:

• What you wear and why the timing of it matters more than the outfit itself

• How to actually run a date so she’s not doing the work the art dealer left on the table

• The exact move for when your banter goes quiet and your brain forgets every word you know

This is some of the key parts I usually only walk my 1:1 clients through, the stuff that turns “great on paper” into someone she can’t stop thinking about. Consider this your fast-tracked version.