Not sure how to deal with my flirtatious boyfriend

Thanks for taking my question.

So a few weeks ago I found out that my live-in boyfriend been seeing three different women behind my back. Two are ex-girlfriends and one is a woman he’s had an on again, off again relationship with for the past 5 years. I found out because we were on a trip together and I saw an email from a strange woman pop up on his phone, and checked it (some other stuff had also happened over the past few months that made me suspicious). It doesn’t sound like he was having an affair with any of them but its very regular, often flirtatious contact.

Over the course of our conversations together, he’s admitted that he saw one of them recently to "confirm his feelings for me." He said her "energy is very different" from mine and he needed to find out if that was important to him.

Another time he was going out of town for a wedding and one of these women was trying to book a flight out together.

I don’t know what to do.

I feel devastated. I completely trusted him and thought everything was great.

I’ve never tried to control him, in fact, most of my previous boyfriends maintained friendships with their exes while we were together and I never had a problem with it. But all the secrecy, and blatant lying... I just can’t get over it.

Also, in the midst of all these conversations, I discovered that he was still in touch with them, which makes me feel ill and wonder if he has some sort of pathology.

Can you help me sort this out?

I have no idea what to think. I’ve also discovered through all of this that he had a long history of infidelity. He’s 38 but has only not cheated on a girlfriend, once. What is the likelihood we can work this out? How would we ever do that?

Fyi on his side, he’s apologized profusely and has said many times that he is committed to making it work, he’s scared of commitment, but he sees a life together. Before this all came out, we’d recently begun to have conversations about marriage and children, which he initiated.


To begin with, it sounds like you are very trusting person—someone who likes to see the best in a romantic partner and tries to work through relational problems in a constructive manner. If this is the case, you probably have a secure style of attachment (see attachment styles).

It also sounds like your boyfriend may have more of a dismissing style of attachment (see attachment styles). If that is the case, it may be more difficult for him to be in an intimate, romantic relationship.

When dismissing individuals become more involved in a relationship they also feel the need to exercise their autonomy or independence—by flirting, being unfaithful, or acting more distant. This is NOT done at a conscious level of awareness; rather it is an emotional, unconscious reaction.

And some dismissing individuals actually view love as a game—where the goal is to play with other people’s feelings. By playing games when it comes to love and romantic, dismissing individuals keep their partners at a distance, which makes them feel safe (see ludus).

This is why it is critical to IGNORE what people say and instead WATCH what they do. Especially in your situation, if you have a secure style of attachment, you are much more prone to wanting to believe positive things that your boyfriend says to you. You are much more likely to try to forgive him and try to work things out.

And if you are generally a trusting person, but you are now starting to have doubts or suspicions, then that is a pretty good warning sign. Trust your feelings. Reflect on the situation.

You boyfriend has cheated in the past and is being flirtatious with other women. While no relationship is perfect, is this how you want to live?

In other words, imagine that you won’t be able to resolve this problem with your boyfriend—is your relationship worth keeping despite the fact that he may cheat on you?

Don’t expect him to change; decide if you are happy enough with things as they are.

The following articles may also help you find the answer you are looking for:

Hope this is helpful.

 cheating boyfriend | dismissing attachment | ludus | lying boyfriend | troubled relationship | worth saving

Other Options:

  • View all tags (specific issues)
  • View all questions listed by topic (broader focus)

I have my own question to ask

Truth About Deception – back to our home page.