He’s sending pics to other women

Have a good weekend.

I’ve been an avid reader of you're column ever since I moved to Boston. I never thought I would write in myself, but, that seems to be the way of things. Here is my dilemma:

I am a 30something woman who has been in a relationship for 3 years. We met out in the mid-west. We were both in grad school at the time. We knew from the start of the relationship that I would be moving to Massachusetts at the end of that first year, and he was OK with that. We agreed that we would see how things went. When it was time for me to move, he said he wanted to make it work long distance. I agreed. I was totally, madly in love, and believed he was as well.

That year apart was one of the hardest I've experienced. But we made it work and were able to see each other at least once a month. We maintained the relationship because we both wanted it to grow. We had talked about trying to live in the same city again, since we still both wanted to be together. But he continued to explore jobs in places I wasn't, and to make a long story short, I started to wonder whether he was being faithful and if he was serious about moving ahead with the relationship. One day while he was visiting and had his computer out, as much as I hate to admit this, I looked at his e-mail. What I found completely astounded me. Not only had he been planning dates with a woman who worked at a company where he was hoping to get a job (and later found out that he went on a date with her, and they kissed), but I also found that he had been sending naked pictures of himself to his ex-girlfriend (whom he always denied having contact with), and had also carried on a serious e-mail flirtation with a classmate of his. I was devastated, as he was always saying how he would never cheat on someone, because he had been cheated on. He had good values. Was from a good family. I didn't get it.

He begged me for forgiveness and again said he wanted to make it work. He moved to Boston to show how committed he was to changing, and attempted to find jobs here. We moved in together, and began the long and arduous process of healing and moving forward. I did end up forgiving him, and we had many, long talks about what happened and why. He said he had been miserable at the time because he couldn't find a job, felt worthless, etc., and ended up cheating. He was going to go to counseling, but never did. I had wanted to marry him and he said he wanted to marry me. But, for whatever reason (he said financial) the ring never came. Still, things were going great this year, and I was happy. I thought we both were.

Fast forward to a few weeks ago. He still hasn't been able to find the job he wants out here (but has been able to work from home this past year). I again checked his e-mail while it was open (which I hadn't done all year). I again discovered that he had been sending naked pictures of himself to women, only this time it was to strangers he had found on Craigslist. Again, I was devastated.
So here we are again. He still wants to make it work, but I don't understand why, or if I want to go through this all again. I've been wanting to get married and begin that part of my life for a while now, and while I still love him, I fear that this person is for obvious reasons, just not the right person for me.

Is it possible to move on AGAIN after something like this? Is it likely it will happen again? Should I give him another chance? He started going to counseling this time, because he says he too wants to figure out why he has done these things, and prevent them from happening in the future. He has been ring shopping, and says he wants nothing more than for us to be married. I don't understand the motivation behind cheating, and wanting to maintain our relationship. I fear that I know the answer to my questions, that I will never be enough for him, but just don't know how to start all over again by myself.

– Confused and Afraid To Be Alone, South End

I don't know whether he'll send pictures of himself to strangers again (although, if I were a betting man, I might put some money on it), but I do know that rings and a lifetime commitments should not be on the table, CAATBA. I know you want to get married, but you have yet to make this work. It didn't work long distance. It hasn't worked with him living in the same house.

People who are just out of school and can't find jobs are often miserable and insecure. But -- that doesn't mean everything he's done is about his temporary situation. And it certainly doesn't mean all should be forgiven.

You're telling us that you know what you have to do but that you're afraid of being alone. I get that. But I would think that spending more time on a guy who isn't marriage material might be scarier than trusting your gut.

If you need to give him another chance before walking away, fine. But marriage shouldn't even be in the mix until you've had a good relationship for longer than you've had a bad one. At the moment, you're not even close.

Readers? Should she give him another chance? Is this about his unemployment? What’s with the ring talk? Should I run some updates on Monday? Because I think I want to. Now help CAATBA.

– Meredith