Go on More Dates and Build Your Dating Experience Using a Quota

Calendar for Going on a Date a Week

Going on a date a week is a great way to build your dating experience. Setting a quota will take focus off of your missteps and keep your eyes on your goal.


It’s been a pleasure helping you through this dating stuff so far. Can you believe this is our 17th letter?! I’m very pleased with our conversations regarding your progress. You’re a terrific guy and you will make some lucky girls very happy soon. That’s right I said girls, with an “s.” That’s what I want to talk about today. You should be casting a wide net and courting multiple girls.

Chances are, James, that even with these new lessons you’ve learned, you will still have more misses than hits. It’s kind of just the way it goes. Therefore you need to stack the odds in your favor via VOLUME.

Dating Is Like Sales – Set and Hit A Quota

I’ve compared dating to sales a couple times in these 17 letters, and I will forever. Sales is my “slight edge.” My secret weapon. My sales experience taught me that it doesn’t matter if I get a thousand nos as long as I hit my quota.

Your quota is modest James. For now we are going to set it at one date per week. That’s only 4 measly dates a month.

Quotas are great because they have a way of taking the focus off of your missteps and keeping your eyes on the goal.

As you learned this past week, there are a million ways to screw up with girls. I can’t just teach you the magic trick that makes them swoon because it doesn’t exist.

You will probably have to encounter all these mistakes on your own. I can’t help you avoid them. Besides, experience is the best teacher.

What I hope these letters will do is help you SEE them when they happen, so you can do in a couple months what took me years.

I had no mentor James. I unwittingly made the same mistakes four or five times before I saw a pattern. Girls do not just go, “Hey bud, I thought your socks were cute. But using a line to get my number came off as timid and you do this upward inflection with your voice that doesn’t come across as very confident. Did I mention I hate uncertainty?”

I had to do a lot of guess and test, but you can catch yourself doing these things. I am happy to help how I can.

You’re like a lot of men that started down this path of wanting to learn how to woo women. You don’t want to be a jerk and play all the girls. You honestly have good intentions. I know. I can tell when we talk and you ask me stuff like, “Is it messed up to text two girls at the same time?”

Well James, since one of them stood you up and has not responded to your texts and you haven’t ever texted the other yet, I think it’s a safe bet no one will think less of you for texting them both at the same time.

It’s Okay To Fail

It seems like I’m rambling but I’m getting to the point now.

As a necessary part of learning to talk to girls you will have to:

  • Take a lot of L’s
  • Deal with a lot of what-ifs and time wasters
  • Cut a lot of girls loose that you really like because you just screwed up at some point

That’s why I want you to cast a wide net. This is not the time to get invested in one or two girls.

You have some skills that will set you apart from other guys and make you better. But for every step of the process that you conquer, there is another one waiting.

After you master dating entirely, then you have to look at the next step: the mid game. How to keep her interested. What about a relationship? On and on it goes. You never stop learning.

You’ve spent over a week focused on one girl who checked you out at a party. That didn’t pan out, and you should know that MOST won’t. Especially not while you’re still learning.

But think if you had been simultaneously texting another girl who wasn’t so flaky. While you were waiting to see which way the wind blew for girl A, you actually could have developed a great relationship with girl B.

That’s what we want to see.

It’s not a big deal how many L’s you take as long as you learn from them. Don’t be abashed by any missed opportunities. Just hit your quota anyway.

Your goal at this point is to go out on one date per week. That is it. You have the resources. I’ve offered you the tools.

I don’t care how you get the dates. You can score an easy date on Tinder. Meet them at a party. At a coffee shop (like in Chapter 23 of Hang-Ups and Hangovers). A quota will force you to find ways to make it happen.

One Date A Week Is Not A Big Deal

Just get one girl to agree to have a drink with you per week. That is your assignment.

When you have a quota, you’ll be surprised how much more efficient you become. How much more capable you are than you thought before. And you’ll realize that NONE of this is a big deal.

Texting two girls at once (gasp). Going on a couple dates a week. Being intimate (kissing or otherwise) with a couple girls a week. It’s not a big deal.

Treat Dating like sales get more dates

Treat dating like sales and you will find yourself going on more dates and caring less about rejection.

One time I was visiting a friend in Raleigh. I swiped on Tinder while we were out that night. I woke up the next morning to some matches. I messaged one and I met her for lunch before I left Raleigh.

One time I was visiting a friend in Columbia, South Carolina. Same thing. I swiped while we were out, woke up to some matches, picked one and asked her to lunch. It’s that simple.

You don’t have to marry these girls. A date is not a big deal.

The comfort you develop from asking a lot of girls out will convey confidence all over the place. Because at that stage you’ll know it’s not a big deal to go on a date, and you’ll communicate that with your entire being. That confidence and attitude will take you far.

Don’t Take It Personally

When I first got in sales, I was super nervous. What if the customers ask me a question I didn’t know? What if they call me on my bullshit or say my price is ridiculous? How will I handle that?

After the first couple customers said, “sorry, not interested,” I realized it’s not a big deal. Because every so often I was getting customers who were super excited about what I offered.

Hearing “no” mattered less and less. My feelings stopped getting hurt.

And when you find someone who truly appreciates what you offer them, you could give two shits about all those past uninterested customers.

That’s it for today James. I’m excited to hear about the adventures your quota takes you on.

Good luck,


About the Author Kyle Milligan

I'm Kyle Milligan, I write New Adult Books that don't suck. i.e. The Hang-Ups and Hangovers series. I like to write about the challenges of being a single twenty-something in today's hookup culture. My blog offers Dating Advice For Men.

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