0105 – How to Be a Mistress” Part I


We’re talking about the being the woman on the side in this two part series from the ‘other person’s’ perspective.


By the end of this episode:

  • Famous Mistresses
  • Why people take a mistress/’Side person’
  • Types of mistress takers
  • WikiHow’s “How to be a side chick’ article

Describe the problem

Segment #1

Mistresses in History

  1. Jamie Grubbs (Tiger Woods), Rielle Hunter (John Edwards), Marilyn Monroe (JFK), Anne Boleyn (Henry VIII), Monica Lewinsky (Bill Clinton)

Why take a mistress? Business Insider Article:

  1. Here is the wild ride of confidential abuse I have been privy to: “She used to pop pimples on my back when we were making love.”, “If we had a party, she would show up thirty minutes late (also a timeline for nights out) and I would have to entertain or wait.”,  “I only got a blow job three times in our marriage – and the last time was the night before I was served with our divorce papers.”, or, my favorite, “Sex was so Goddamn boring – I just couldn’t crack the code . . . “.
  2. This may sound outrageously simplistic. I am just a mistress after all. The reason men love me? I will tell you. Before I go to meet any one of my lovers, I have one thought in my mind: Please let me please him.

Three Types of Cheaters

  1. The Incessant Cheater (The Charmer)
  2. The Unbelievable Opportunity Cheater (Not looking to cheat)
  3. The Discontented Cheater (Feel Justified)


[message break]


Segment #2

How to Be a Side Chick-WikiHow

  1. Keep things interesting. When he texts you, keep the conversation interesting. A side chick’s main responsibility is to keep things fun and exciting. Giving him short answers and acting uninterested will make him wish he was playing Words with Friends instead — or even just hanging out with his Main. Tell him funny stories; ask how he’s feeling; surprise him. Do whatever you’ve gotta do to keep things exciting, as long as it feels natural.
  2. Don’t ask questions. This should be a no brainer. You can’t ask “Where were you,” “Why didn’t you call me,” “Why are you always so busy,” “Why don’t you ever see me,” “Who were you on the phone with,” etc., if you expect to keep the relationship going. These are not side chick questions. You got yourself into this situation, and there’s no point in acting jealous or surprised when you already knew the score getting into it.
  3. Don’t try to spend holidays or birthdays with the guy. If he cares enough, he might celebrate these events with you the day after or before, but for the most part, don’t expect anything like a gift or acknowledgment. These days are saved and reserved for the Mains, and it may be safe to text him to wish him a happy New Year/Christmas/birthday, but a phone call should not be made. And as for Valentine’s Day, you can pretty much bet that he’ll be spending it with his main.

Final Thoughts:

Let him think he’s the only one. You don’t want him to think you get down like this, even if you do. You’re already a side chick; you don’t want him to think you’re seeing other guys, too. But if you are seeing other guys, then so what? You have every right to do what you want; he didn’t put a ring on your finger, did he?

  • Keep your Facebook clean. Don’t let him see lots of pictures of you with a bunch of other guys.


  • Elijah’s Thoughts
  • Sarah’s Thoughts


In Closing

If you have a question, comment, or funny story about [INSERT SHOW TOPIC] we have a private SafeSpace on facebook where we talk about all sorts of social, professional, and romantic relationship topics, and after every show you can go there and share you story, get some advice from great people or just hang out. Both Sarah and I are there every day and you can be there too, just go to www.relationspodcast.com/join and click the “Join Now’ button.


Until we meet again, keep striving to make every relationship you have the best it can possibly be, including the one with yourself. We’ll talk soon.

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