Pro Tips: The Psychology of Getting Free Shit- Pt. 2

The first reason people fail at getting free shit is because they try and get the wrong things from the wrong people. Even worse- they don’t know what they want, nor who can give it to them.

The second reason is that their attitude sucks.

If you read Part 1 then you’ve already mastered the art of your own behavior.

But before break it down for you, I must give you the harsh truth. There are only two situations which ever result in getting free shit.

  1. Its a gift
  2. There’s a problem

That’s right. So here I have lined up a set of behavioral techniques for each scenario.

Scenario 1: Its a Gift

Appearance Always Matters

  • When dealing with people in person, look presentable. Make sure you interact with and greet everyone when you are in tip-top shape. Build relationships when you are the most physically attractive. I make sure the times I have a 15 minute convo at the bell desk are when I’m about to go out for a dinner date and done up.

Be a Regular

  • The more you frequent a spot, the more special you become. People build an attachment not only to you, but to your happiness. True regulars are friends, and friendship will get you very far.

Reward People

  • When someone goes above and beyond for me, I always ask if there’s a customer survey I can fill out to help them. If not, I ask if there’s someone I can talk to about just how positive my experience was with them. This is important especially in hotels. The survey the hotel sends you at the end of your stay holds huge weight. Some companies offer their employees cash bonuses for every time they get a positive mention in a guest review! I left a positive review of a couple hotel staff members that I love, and came back the next week to a room with a flower arrangement. Always show you are loyal and willing to scratch someone’s back. They will scratch yours in return.

Give Gifts

  • This works great in conjunction with or as an alternative to reviews. Bring someone a holiday gift, vacation souvenir, birthday present, or (the best…)  a thank you gift. Write a card too! When two girls at the hotel went above and beyond for me, I told them I wanted to give them a thank-you gift from Sephora. Instead of just giving them something random, I asked them to tell me “one item you have always wanted but just wont buy out of practicality.” Every week since then they have sent me champagne and chocolate covered strawberries.

Be Everyone’s Funny Friend

  • Crack jokes whenever possible. Even in the shortest of interactions. Everyone loves a good light hearted self-deprecating joke. It’s vulnerable and relatable.

Remember Names

  • It is even better if they see you write it down. I always ask someone what their name is then proclaim, “Hold on!” as I get out my phone, “I’m going to write this down because I want to remember this.” Then address everyone by name when you see them. If you think you have forgotten, say “Wait, let me try and remember… ugh!… Mike?” That way if you are wrong they know you really wanted to remember. If you are wrong, apologize and write it down. Then restate your name without giving them a chance to think about it. It shows there was no expectation on your part for them to remember yours. The first time someone remembers your name, make sure to reward them with happiness and excitement. Even better if it is surprise. Humility is important.

Break the Touch Barrier

  • Especially if you are a regular and see them often. If you feel awkward the first time, you can say you had a hard day and need a hug. From there, make it an expectation. Hug them every time you see them. Hugs are for friends, and friends get taken care of.

Act (Almost) Uncomfortably Familiar

  • People love vulnerability, even if it scares them at first. The easiest way to become someone’s friend is to treat them like a friend. This works really well in super formal or uppity environments where you will seem like a breath of down-to-earth fresh air.

Scenario 2: There’s a Problem

Be Sad, Not Mad

  • People hate angry, demanding behavior. Saying things like “this is unacceptable” is a death sentence.  God forbid you threaten someone! The right attitude is one of sadness or disappointment. People are more likely to try and cheer someone up than calm someone down. When you’re upset, people see it as a chance to do the right thing. It inspires sympathy- and sympathy inspires action.

Meet Them Halfway

  • This is possibly the best tip I have, and a highly underused one. Let’s be real, if you aren’t spending any money, it is going to be very hard to get anything worthwhile in return. Offer to pay half, or say “well what is possible for $25? That’s kinda the budget right now.” You may get more in return than what you expect.


  • When things go wrong, you are more likely to be rewarded if you have evidence. Know who you spoke to, keep receipts, remember what day you ordered something, etc. Know the facts. When my DSW order arrived at the hotel one day late, I called customer service ready with my order number, time it was placed, and when the expected delivery was. I got the 2-day shipping I paid for completely refunded, and still got the shoes 5 days earlier than I would have with free shipping.

Don’t be the Problem

  • Whenever possible, express that you are only upset because someone you are with is upset. It makes you look empathetic, and takes the blame off of you. Make someone feel like giving you free shit would help you save face.

Offer to Pay (even though you don’t want to)

  • “Ugh… do you think you could just put in an app so it will arrive at the table when we get there? I don’t care what it is, you can put it on the check or whatever I’m just trying to think of ways to make up for this.” The odds of it getting comped are very high.

Make Your Circumstance Important

  • Assert “I wouldn’t normally care, but this is a special occasion!!” Or… you are going to be late, this is your first time there, you had a particularly bad day, you had a particularly good day (until now!), you are visiting from out of town…. It doesn’t really matter what, but if you make something seem special, people will treat it with more importance.

Sound Hopeless

  • This shouldn’t require an explanation. There are times where promoting a solution to a problem works best (the solution being getting free shit), and there are times when acting completely demoralized works best.


  • Get awkwardly vulnerable. It’s not just that the hotel forgot to send up the champagne, it’s that the champagne was for you and your boyfriend and you have been having lots of relationship issues lately. Maybe your sex life is shit, maybe you are falling out of love. Make people feel awkward and they will do anything to shut you up, and shut you up fast.


  • Outright ask for things. When Jamba Juice’s loyalty system went down, I contacted the franchise owner and asked him to honor the company rewards system based upon  my dollars spent. I ended up getting rewards for 3x the amount of money I spent.

Thanks for reading Part 2! Look out for the next installment, where I will run through what to get and how to get it from restaurants, hotel, airlines, and more. Hope you enjoyed this! Until next time.




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