Then Jack Happened


Dear Jack:
I’ve been dating a man for the passed three years and I have a confusing situation. He is extremely successful and runs his own business. I moved with him cross-country then from another city to the next. We live together in a house he bought. I have just started adjusting to my new city, got a job and some friends, but he is never around because he is traveling a lot for work. He told me the other day that he was ok with me dating other men, that he wasn’t going to date other women and that is just how it is when you are dating a big business owner. He said that he had this arrangement with his previous girlfriend. I am ok with him traveling and being absent a lot but I want to be in a monogamous relationship. Do you think this situation is salvageable?
I figure you can look at his plan one of two ways. Either he is into having an open relationship as he has clearly stated, which will be a problem because you want a monogamous relationship. Or, he’s throwing out the idea of an open relationship because he isn’t terribly into you but wants to maintain the current course of things for whatever reason. Either way, you should have another talk with him about what your long-term goals are for the relationship before you end up expending more time on a relationship that might not be going anywhere.
One part of your question I find interesting is that he told you ‘that is just how it is when you are dating a big business owner.’ Far be it for me to assume what it’s like to date and live with a ‘big business owner,’ but I tend to disagree with this kind of wide brush kind of logic. At the end of the day, what he is talking about is what it is like to date HIM not just a ‘big business owner.’ The ‘big business owner’ statement is just a way to deflect responsibility away from what he really wants. The other flag is that this is how he did things with his previous girlfriend. Emphasis on ‘previous.’ This might just be the first step he takes to passively indicate an end to the relationship. That’s why I tend to believe that he really isn’t as into you as you might think, or, he just doesn’t prioritize your relationship above what else he has going on in his life and he’s ok just keeping you at the house.
And honestly, that’s ok if he is up front about his true feelings and opinion of your relationship. If you are satisfied with the status quo and decide to let it go then that’s up to you. But if you are curious if he is actually saying what he means and you aren’t completely comfortable with your relationship’s status then you need to talk to him about your concerns and clarify exactly what is going on. Be direct, be honest, if he is still unclear or evasive you have an indication of his true opinion. Those conversations can be difficult but they are necessary to make sure that you and your significant other are on the same page, or to find out if it’s time to move on from a disintegrating relationship.
Delray/Boca, I’m ok with you seeing other people, but only if you promise to send me—and only me—your questions at