Five Dating Hacks for the Non-Douchiest of Men

The founder of the League on how a gentleman does romance

By Michael Nolledo

Five Dating Hacks for the Non-Douchiest of Men
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19 December 2016

Contrary to what dating apps claim, there is no shortcut to love.

Because with dating — like everything else in Chicago — you’ve gotta put in the work.

Still, the right dating app wouldn’t hurt.

And by right, we mean the League, the invite-only dating concierge for the well-heeled and well-to-do, now taking applications in Chicago.

For the uninitiated, the League is the private members’ only club of dating apps, where, to find your perfect mate, you’ll have to go through a rigorous vetting process that screens your education, occupation and social media influence.

Less than a month launching in Chicago, the waitlist counts 13,000 and rising, with a “Founding Class” of 2,000 that includes creative entrepreneurs and CEOs alike. Point is, should you wish to sign up, prepare yourself for judgment day.

To help you stand out from the crowd, we asked founder Amanda Bradford for a few tips on dating, romance and more, which is like asking the head of the SEC for stock tips. So, listen up.

Choose a venue that’ll keep you both active.
“Interactive dates are better than interview dates. Find a spot that has a little something extra, whether that be bocce ball and billiards at Game Room or Yahtzee and Battleship at Guthrie's Tavern.”

Skip the table and sit at the bar. 
"Chicago's a great drinking town, so sitting at the bar will make her feel like you're on the fifth date. And you don't want to be that table that screams "we're on a first date!" Plus, your legs may touch accidently. Sitting next to each other sets a much more casual tone while being a lot more intimate."

Check your ego at the door.
“We cater to busy, high-achieving people, and while many sources will say not to talk about work on the first date, we say talk about it. But be careful. Your date isn’t concerned about your day-to-day tasks or how much money you’re making. She’s interested about what excites you about going to work each day and how you got into your industry. Rule of thumb: if you start talking about work at the beginning of a round of drinks and are still talking about it when you’re both almost done … you’ve discussed it for too long. Move on."

Don’t mate on the first date.
"Let’s be honest: you won’t lose interest in someone based on the fact that you had sex on the first date. But bad sex on the first date? Dealbreaker.  It’s not about holding out, or making sure that you’re being respectful or respected … isn’t it really all about good sex? If you have a good first date chances are there could be chemistry there, and with better chemistry comes better sex. Hold out for the better sex."

Don’t ghost. Just don’t do it.
Ghosting (aka phasing out a relationship by simply not replying to calls and texts) is the most common way to break up these days, because it’s an obvious signal and both people can move on quickly. Trust me. It'll only come back to haunt you. Chicago is a small enough city and there is a pretty good chance you will either A) run into each other again or B) try to go on a date with one of her friends. The repurcussions are not the worth the silence."

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