Bad news

Dear Dr. Lovemonkey,

I’ve been going out with a guy for a couple of years now, but it’s a little complicated. He lives with his girlfriend and we’ve been seeing each other on the sly all this time. A while back, his girlfriend got pregnant. She didn’t tell him for at least three months. The night that she had the baby, he came and stayed with me. I felt lousy about it, but he told me that he loved me and wanted to be with me.

The fact is that I do love this guy. I get the sense that if he could get out of his current admittedly complicated situation, we could start over and be happy. On the other hand, I feel guilty about the way this whole thing has developed. What do you think?

— Seriously Confused

Dear Seriously Confused,

Pull back a little bit and think about this. Here’s a guy who’s been operating for a number of years in a completely dysfunctional relationship. He’s been consistently lying to his girlfriend by being with you. She obviously doesn’t trust him because she didn’t share the information with him when she became pregnant. It’s a pretty bad scene, yet he didn’t do anything except continue with his deceptive ways.

This is much more than "complicated." He’s now a parent and shares a lifetime of responsibility for this child. It is not a situation one extricates oneself from and there is no "starting over." Think about the pathology of a guy who behaves like this. He’s bad news. Your relationship with him is bad news. Break it off and find someone who is not about lying, cheating, and refusing to face responsibility. That would mean someone who isn’t currently involved with someone else.

Dear Dr. Lovemonkey,

I’m a 29-year-old man who has never been married. For the past year and a half, I’ve been going out with a divorced woman who is 37 and has a 15-year-old son. Her ex-husband (they were divorced four years ago) is wealthy and owns his own business. While they were married he set her up in a business of her own that she still runs.

She is very attractive. Besides her ex-husband still being in her life because of their son, I’m aware that he’s still interested in her and would like to get back together with her. He was a very controlling factor in her life and this is one of the reasons that they are not together. He casts a fairly large shadow.

She tells me that she loves me and wants to be with me. She doesn’t, however, discourage the attention she gets from her ex and the other men who regularly come on to her. She’s not cheating on me, but I can tell that she enjoys the attention. She also enjoys the privileged sort of life she’s gotten used to since being married to her ex.

I don’t make a whole lot of money and won’t ever be able to compete in that aspect of life. I am considering asking her to marry me, but I don’t think it would work unless she changes a bit. Is this asking too much? What is the likelihood that she could switch gears to be happy with someone like me?

— Ed

Dear Ed,

It doesn’t seem to me (and it sounds like it doesn’t seem to you) that your girlfriend is likely to embrace a decidedly different lifestyle from the one to which she is accustomed. That doesn’t mean it can’t or won’t happen, or that you can’t try to develop a life that can be mutually satisfying. You haven’t given me any indication, though, that you’re both committed to each other in that way.

I would suggest you continue with your relationship and perhaps begin discussing very seriously whether this could work. My guess is that your girlfriend is reasonably satisfied with things the way they are and that there would have to be some sort of serious change of heart for things to work out. At this time, marriage doesn’t seem to be a wise step.