4 Ways Hang-Ups and Hangovers Can Keep You From Hang-Ups and Hangovers

There are TONS of relationship and dating self-help books and they all say the same things: “Hold frame. Put yourself first. Have confidence.” What does any of that stuff mean, practically? That’s when I decided to write a novel showcasing the details of a personal dating journey and evolution told through the eyes of David McCleary with Hang-Ups and Hangovers. To show you the real anxiety and inner monologue of a man trying to approach and talk to attractive women. And along the way I dropped some wisdom.

The 4 core concepts David McCleary learns in Hang-Ups and Hangovers are tried and true for attracting the opposite sex. If you follow these rules, you’ll have a shot at avoiding hang-ups and hangovers yourself.

Those 4 concepts, listed in order of importance are:

  1. Eye Contact
  2. Abundance
  3. Self Amusement
  4. Shamelessness

Eye Contact

I can’t stress eye contact enough. It is the foundation for everything. Nothing else can happen until you nail this down. It’s difficult to have a connection with a person unless you can look them in the eye. It makes it harder for people to like and trust you. That doesn’t mean lend someone the penance stare, but don’t look away when you’re talking to someone. It feels shady. Weak. Practice on the people ringing up your groceries at the store. It makes a ton of difference.


This is another one of those “foundation” things, but goes a little deeper. Eye contact is important, especially at hello, but abundance keeps you in the game. The idea behind abundance is that you understand and are intimately comfortable with the FACT that the world is abundant with opportunity. i.e. other suitors. Basically this gives you permission to BE YOURSELF.

The old, “be yourself” line is both one of the most helpful and misguided lines of advice in the book. Of course you should be yourself, that’s how you discover if the person you’re talking to is a good fit for you. If you’re pretending to be someone you’re not, the gimmick will eventually fade and things will fall apart once the mask is off. In order to truly be yourself though, you must first be totally cool with the other person walking away and saying they didn’t find you very attractive or interesting. Knowing that there are myriad other people in the world available for you if this one conversation fizzles out makes you relaxed enough to truly behave as you would, say, sitting with close friends at the bar. That’s what abundance is and it’s critical for finding someone who is truly a match for you.

Self Amusement

Easy. Talk about shit you enjoy! If it bores you, don’t talk about it. Even better, say “that shit is boring.” Be honest. That’s part of fully grasping abundance. The reason you want to talk about things you like, or self amuse, is that it is conducive to you finding a match who truly complements you as a person. Be a little selfish, it’s for the greater good. If you talk about things that make you laugh and smile and the other person is not laughing and smiling with you, chances are that person would make an uncomfortable date. So do yourself a favor and talk about things that you like. If they aren’t into it, you just saved you and them a lot of time.


You can’t always talk about things you enjoy unless you are shameless. You kind of have to be like Tucker Max on this one, or Kanye. They have no shame. Shamelessness is important on so many levels. First, if you consider one of your favorite pastimes to be a “guilty pleasure,” you might be hiding the one thing that truly brings you and the other person closest together as people!


Girl: So what do you write about?
Me (embarrassed by the sexuality in my books): Um, ya know this and that.
See how unrelatable?

Girl: So what do you write about?
Me: Mostly modern dating for 20 somethings. A lot about today’s hookup culture.
Girl: Really? Dating today sucks. I’m over it.
Me: Yeah? What was the last date you went on like?

If you’re embarrassed or insecure over something about yourself, it will show and it will turn people off.

Here’s some rules to live by:

  1. People are flawed, and they only connect to each other through their flaws. Show yours. And don’t be ashamed.
  2. People will only make a big deal out of the things you make into a big deal.

I go into painful detail and show examples where my main character, David McCleary, slowly comes to accept these 4 concepts as true, through trial and error. You’ll laugh, you’ll cry, you’ll grow.

The sequel to Hang-Ups and Hangovers, Redheads and Bedspreads, expands upon David’s experiences and new knowledge into an even grittier part of navigating today’s hookup culture.

Feel free to check out all my books!

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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