He flirts with other women

I have been dating the greatest man I’ve ever met or could hope to meet for almost a year. He is a very outgoing, friendly person, but often crosses the line of what I and others see as flirting. The vast majority of his friends are female and he has a pretty expansive past in terms of number of girlfriends. This combination makes me pretty uncomfortable.

I know I need to accept who he is and also his past, but I think that I’m having trouble accepting this because I’m either insecure, possessive, or both and I am having trouble trusting him. I know he loves me very much and I love him very much and there’s no reason for me to feel this way. What can I do to get over these feelings?

We have an otherwise very open relationship and talk about everything, but I have trouble talking to him about this because I know it is just my insecurity and he’s not really doing anything to warrant it and I don’t want him to know how insecure I am.


From what you say, I know few people who wouldn’t react with some degree of insecurity in a situation like you describe. Unless you have a history of being particularly possessive or insecure, to an extreme, I wouldn’t think that some insecurity is out of place here. There is nothing wrong with being insecure.

Trust will not develop from hope or wishing for it. It doesn’t come from thin air. It should not be an assumed commodity in relationship. It’s okay to be willing to trust, but foolhardy not to realize you may not have enough information or experience yet to know if you can really trust.

Actual trust comes from actual experience. It comes especially from facing challenges together and overcoming them. In this way you learn if you can trust your partner. You find out how they respond to difficulties or challenges. You learn if they are only around for the good times, or if they can go the distance and deal with problems, too. And since we all know that problems and issues are inevitable in love (we do know that, don’t we?) then at least some part of us needs to find out how our potential soulmate responds to difficulties.

It may be that part of what makes this situation hard for you is that you are not talking about it. If you are silent, you leave the challenge untested and you don’t find out how well the two of you can show up together and resolve it. It remains unresolved. We may hope that time cures it. But how is that going to happen?

I’d go ahead and talk to him about your feelings. You will find out, then, if you can trust him by his response. If he listens to you and accepts that you do feel the way you do and is compassionate and assuring towards you, then you will gradually learn you can trust him. If, on the other hand, he gets defensive or says it’s all your problem, then, unfortunately, you may find out that there are some trust issues at hand to be resolved.

Eventually you will need to bring up and explore this with him if you ever want to establish a deeper and more authentic relationship. Of course, it would be best to state your insecurities as you do to me, here in this email, as emotions that you totally own yourself, rather than accusing him of making you feel that way. The more you can own these feelings as yours, the easier he will be able to hear you without having to defend himself.

Successful intimacy includes being able to share some of our deeper and less pleasant emotions with each other, and that being okay… that we can find out we are accepted by the other as a whole person (which includes feelings like insecurity) rather than having to just show up in a positive light all the time. At one year together, it is more than appropriate to reveal more of who you are, in the spirit of honesty and healing and taking the relationship to the next level of depth.

Based on over 20 years of working with thousands of people to heal their relationships in my marriage retreat, I have written a relationship help book you can download now or get in print. In my book I share many tools and methods for learning to do this kind of sharing in a skillful, positive and productive way. I also discuss what I am referring to above, becoming more whole, and healing our old baggage and parts of ourselves that get triggered or afraid in relationship. And many other things, too, like how to develop your shared vision and how to do emotional healing work together.