Cheating Problems

My New Man has a History of Cheating!

I like this new guy, but he has a history of cheating.  Am I setting myself up for disaster?

If you’re in a new relationship with a man who has a history of being unfaithful, you may be wondering if he’s actually a good choice to pursue.  Knowing his history of cheating will likely make you suspicious of his behavior right from the beginning.  However, people can change in the right circumstances, and if you think this might be the man for you, proceed slowly and talk to him about the following things:

  1. Understand His Previous Relationships

You know he has a history of cheating.  You need to understand why he cheated.  Ask him about what was going on in his past relationships when he opted to cheat.  Usually there is a reason for such behavior.  Maybe he wasn’t in love anymore, or he wasn’t satisfied in bed.  The more you understand what caused it in the past, the better you can understand how to keep it from happening in the future.


  1. Ask Him To Be Transparent

Let him know that you have concerns about his past of cheating and that it makes you nervous to begin dating him. He needs to be transparent with you.  Let him know you need to build up the trust with him, and you need him to be as open and honest as he can possibly be to show you that you can trust him.  No little white lies – as harmless as they seem when he tells them – it will make you suspicious of anything he says.


  1. Open Up

Make sure you keep the communication lines open throughout your relationship.  If one of the reasons he cheated in the past was bedroom boredom, ask him what sort of things he’d like to try out with you.  Keep it exciting.  The most important thing is good communication.  Don’t keep things bottled up.  If there is tension in the air – clear it.  Being in a relationship where he feels free to say what he wants, and knows it will be respected – will keep him happy and less likely to stray.


  1. He Can Change

There are many people out there who had a history of cheating and are now in faithful relationships or marriages.  When men cheat it is often because of something wrong in the relationship.  All it usually takes is a truly great relationship to make your man settle down.  If you are the right one for him – he won’t want to stray.

Define… “Cheating”

Define cheating as a couple to make sure neither one of you make a mistake.

It seems that there used to be a definition of dating many years ago.  The lines were clear and it was easy to judge what was and was not allowed.  Over the years, people have become a lot more open about their sexual relationships and desires, and relationship boundaries are often ‘smudged’.  When you get into a relationship with someone, you need to clearly define cheating and what you both believe it is.

Some questions to start with may be:

Is it cheating if either one of you….

  • go to the strip club?
  • get a lap dance?
  • have coffee with someone you find attractive?
  • go to dinner and a show with someone you find attractive?
  • cuddle with someone?
  • kiss someone while playing a game of truth or dare when you are both present?
  • kiss someone while playing a game of truth or dare when the other person is not present?
  • dance sexually with another person at a night club?
  • lightly kiss another person?
  • passionately kiss another person?
  • have phone sex or cyber-sex with another person?
  • kiss a celebrity?
  • kiss or make out with someone of the same sex?
  • give oral sex?
  • receive oral sex?
  • you have sex with someone vacation?
  • watch porn?
  • masturbate while watching porn?
  • get a ‘happy ending’ massage

The list can go on forever, which is why it’s important that you sit down together and make a clear outline of what is cheating and what is not.  Some women don’t mind their man going out with the boys to a strip club, but may draw the line at getting a lap dance.  Some couples have a list of celebrities that if they ever had the chance (highly unlikely in most cases)they would be allowed to have sex with.  Many couples take it further – and allow their significant other to have sex with other people as long as they know about it.

You don’t know what type of relationship your man is used to being in, and vice versa – so you must define cheating in your relationship at the beginning so nobody gets hurt.  You may not agree on everything, but that’s okay – you can always compromise – just make sure that if you say it’s okay, you mean it.  And don’t stray from the rules you have set up.