Ask Amy: Relationship strained by chronic cheating

DEAR AMY: My boyfriend and I have been together for two years. I am 26, and he is 49.

He has been married and divorced twice.

I have heard from his friends that he has not had a great track record with being faithful. My boyfriend’s response to this is that I should believe him over his friends.

I have just recently found out that he has been having an affair with another woman (whom he works with) for almost a year.

Amy, I am completely broken. I cannot eat or sleep. He came crying back to me, telling me he wants to make things work with me and wants me to move in immediately and get married!

I am not sure what to do. I have absolutely no trust in him. He has said he will do whatever it takes to make it work. He has suggested counseling (which he never did in either of his marriages) and he has even suggested that we have tracking apps put on our phones so I know where he is at all times.

Even with all of this, I do not know what to do. A part of me feels like saying “once a cheater, always a cheater,” but the other part tells me to give him a chance because I still love him very much.

Back to homepage

Subscriber Login

Keep reading with a digital access subscription.

Subscribe now

— Cheated On

Dear Cheated On: Not to put too fine a point on it, but if a 49-year-old man with a cheating history can’t manage to stay faithful to a woman with whom he is in a relatively new relationship, then he is a certified and chronic cheater.

Do not marry him. Do not move in with him. Do not put tracking apps on your phone; this puts you in the position of trying to police his movements.

A new relationship should not have the pressure of mutual surveillance in order to maintain trust.

Your guy should pursue counseling for himself. Pulling you into counseling with him holds the assumption that you two have a relationship problem as a couple. You don’t. He has a cheating problem.

If you want to maintain contact with him, then he should demonstrate over a long period that he has gained insight into his own problems, is committed to change and has demonstrated very real change.

There are so many good men out there who don’t cheat. Don’t sell yourself short, and make all of your future choices in service of your own self-esteem and personal worth.