How Do I Convince Him That I’m Not Like His Ex?

Evan,
I’ve been dating this guy for the past four months. I am 26 and he is 38. We met on Match.com. Both of us are divorced with no kids. We were both in relationships with someone who treated us like we were worthless. Because of that we both have a hard time trusting that the other isn’t going to be like our ex. I have been divorced for over four years. He, on the other hand, has only been divorced for about nine months. I am his first serious relationship since his divorce. He is not my first serious — I’ve had a couple since my divorce. I am not in this to fall in love and get married right away — I am in this to have a companion. Someone to enjoy spending time with and get to know and see where it might go in a few years.

When our relationship started out, it was great! We enjoyed each other’s company, always laughed, had plenty to talk about. Due to the past couple of relationships I have been in, I took my time to get to know this one. It took me over two months to get comfortable enough with him to feel like he could be someone worth pursuing. But it seemed that as soon as I got on board, he stepped off the boat. He has been distant, doesn’t chat as much, doesn’t come around as much.

We’ve had a couple conversations about it. Each time he says he has hit a brick wall. He’s admitted to being afraid that I am going to turn out like his ex. He wants to go out and do things with his friends and things he enjoys, and he thinks I will be upset about it. I told him as long as he makes time for me too, I am fine with him wanting to have his own life. I told him the other night that if he just doesn’t want to be with me, he needs to tell me and let me go. He said that he wants to be with me, but also wants to be able to do his own thing. So how do I get this guy on board again? How do I prove to him that I am not going to turn out like his ex? And most importantly, how do I trust that he isn’t just dragging me along as just a spare time girl? —Jennifer

I have one overriding dating philosophy: Relationships are easy.

Dear Jennifer,

I have one overriding dating philosophy:

Relationships are easy.

All the people who tell you that relationships are “work” are people who married the wrong people and are justifying their bad decisions.

Sorry to say that, but I believe it to be true. Happy marriages are fun, not work!

That doesn’t mean that every second of the day is heavenly. But it does mean that you should get along with your partner 95% of the time, and the 5% you don’t should be resolved quickly and painlessly.

Sounds to me, 4 months in, that your relationship is a little too much “work” for my taste.

You are the CEO of Jennifer, Inc. and your boyfriend is an intern applying for a job with you.

Case in point: “As soon as I got on board, he stepped off the boat. He has been distant, doesn’t chat as much, doesn’t come around as much.”

Then what’s the point of him, Jennifer?

What’s the point of a boyfriend who is distant, doesn’t call, doesn’t make plans, doesn’t make you feel safe, heard or understood, and generally makes you feel like you’re one more thing he has to deal with?

That’s right. There IS no point.

I’m not sure if you’ve read my materials beyond this blog, but if you had, you would have heard me repeatedly reminding you that you are the CEO of Jennifer, Inc. and your boyfriend is an intern applying for a job with you.

He may have gotten in the door because he’s got a good resume and was a solid interview, but now that he’s been working with you for four months, how is his job performance?

“Each time he says he has hit a brick wall. He’s admitted to being afraid that I am going to turn out like his ex. He wants to go out and do things with his friends and things he enjoys, and he thinks I will be upset about it.”

He may be a good guy, my dear, but he’s a shitty employee.

You need a man who arrives at work early and stays late, all with a big smile on his face.

Unfortunately, you’re acting like the intern, who is just begging for her job: “How do I get this guy on board again? How do I prove to him that I am not going to turn out like his ex?”

You don’t. You’re the CEO. You bloodlessly evaluate his work, not based on his potential, but on his performance. Then you face the facts:

Your intern isn’t cutting it.

It’s time to downsize.