Should I trust my new boyfriend who cheated on two of his Ex Gf’s?

Should I trust my new boyfriend who cheated on two of his Ex-Gf’s?

Today’s topic is: Should I trust my new boyfriend who cheated on two of his Ex-Gf’s?

To some people, this question is a no brainer because they just wouldn’t go. there. period. After all “once a cheater always a cheater,” has been one of the most popular cliches ever!

Is this a fair assessment to generalize that everyone who has ever cheated on someone will continue their infidelity traits with every partner?

Is it possible that maybe they were just young and ignorant of how powerful these life choices can be? Let’s all take the time to remember how our high school reputation lingered on into adulthood. It’s not an easy path when mistakes are made in our youth. It can be the foundation of our self-esteem for many years to come.

But the question on today’s post is asking if you can trust your new boyfriend who cheated with two of his exes! He was in relationships with both of these ladies and not in a casual sense, or so they thought. This is a repeated action within two partnerships.

He made this choice to cheat not once, but twice. That is rwo big red flags!

OK let’s give him the benefit of the doubt for a minute:

  • Did this happen in high school or shortly thereafter? (We are still finding out who we are on all levels which include our morals.)
  • He didn’t think he was in a committed relationship and was still dating others. They hadn’t had the exclusivity talk yet.
  • His exes had cheated on him first and he was retaliating.

Now let’s discuss how you know that he cheated with these women and what he has done since to change this pattern.

  1. Did you find out he was a cheater from his exes or from someone other than your new boyfriend? Was he hiding his past or open about it?
  2. How long ago was this? Was it as recent as his last 2 girlfriends?
  3. Was he upfront with you from the beginning of your relationship or were you made aware of his cheating after you had developed feelings for him?
  4. Does he feel remorseful about his actions and takes ownership of what transpired?
  5. Has he had any relationship counseling to get to the root of his cheating? Does he know what led him to be unfaithful to his exes?
  6. How long ago did this happen and has he had other partnerships where he remained loyal to them?

Whenever you find yourself in this scenario you really need to pay attention to your gut instincts. You are asking this question so is there something that is making you feel he will cheat again?

How does he treat you?

  • Is he true to his word?
  • Do his actions match his words?
  • Are you his first priority?
  • Is he secretive about things?
  • Have you met his family and friends?
  • What do others say about him? Is it positive feedback?
  • Has he told you he loves you and shows you regularly?

If he has done some work himself and has changed his ways, do you honestly feel that he has learned a valuable life lesson? Be careful that you don’t go into this new relationship thinking you will be the one to fix him. That is not your job, it is his job.

We all make some bad mistakes in our lives but it is how we deal with them that is the most important thing to how we move on to better ourselves.

A repeated mistake is a choice!

Here are a few questions for you:

  • Have you ever cheated on anyone?
  • How did your past relationships end?
  • Do you have trust issues from a past relationship or your childhood?

Make sure there isn’t a bad boy pattern happening here and that you are repetitively choosing drama-filled partnerships. You may think they are full of excitement but they will bring you nothing but heartache with each encounter.

Everyone deserves a second chance but don’t allow someone into your life at the expense of you having to learn another painful lesson. Trust and communication are the building blocks of a healthy relationship, don’t ignore the value of their importance.

Please leave your comments below! Would you date someone who has a cheating past? What advice would you offer to others?

Sybersue xo <3

Susan McCord @ Dear Sybersue YouTubeDear Sybersue Facebook

Dear Sybersue Blogs & Advice ColumnDear Sybersue Instagram


  1. Pingback: advice column for men & women – Dating Relationship Lifestyle Advice - Relationship Advice
  2. Pingback: 3 Shared Values That Are Essential In Relationships - NewsInGeneralNewsInGeneral

Thank you for visiting Sybersue! Your comments and topic ideas are always appreciated!