We keep breaking up; should I tuck tail and run?

Hey Guys,  

Thanks for having a page like this!

My question is similar to one previously answered but with a twist, a confusing twist. Here’s the background story. ….

I’ve been dating my boyfriend for nine months now and things have been amazing except for a few occasions. It’s been slow going and I think that’s why it’s been so good.  He had just arrived to the U.S. with the thought that he was going to enjoy his time here, party, travel and make new friends. He wasn’t really looking for anyone to date or be in a relationship with. Then we met. (I wasn’t looking for anything serious either.)

One day out of nowhere he started talking about how he hated his job, wanted to up and leave, blow a bunch of money and just travel. After his vent he saw that I looked upset. We had a conversation about what he has always wanted to do and he didn’t think it was fair to be involved with someone if he couldn’t even decide if he wanted to stay in this country for his three year tour. I reminded him that I wasn’t here to hold him back and he could do what he thought was best and  if we were together when he had to go back home in a few years that we would figure that out then and not now, only four months into our relationship. He asked if we could just be friends and I told him I don’t stay friends with my ex’s and he wouldn’t be an exception. We talked some more and he decided that he wanted to continue and take it day by day. I accepted and things went back to being amazing again.

Shortly thereafter he took off for the holidays with his family and I stayed home because I didn’t have my passport yet. When he returned he wanted me to Skype with his parents but I told him I wasn’t ready to meet them yet especially after our discussion before he left. A few weeks later we had the same conversation after having a fun day with friends bar hopping. Not wanting to talk about this in public I walked off to our room we booked prior with him chasing after me apologizing saying it was the booze. We talked about it the next morning and he just laughed at himself and apologized again for ruining the night. Things went back to normal like nothing happened and we continued to get closer and took another trip together. I didn’t expect what was coming next.

We had another breakup conversation soon after. He talked about his fear of commitment, not knowing what he wanted in life, and that he felt like he wasn’t reciprocating back my efforts in the relationship. I told him why I enjoyed his company so much and how I liked the no expectations nature of our relationship. I don’t think he expected to hear how wonderful I thought he was, that I didn’t expect him to take care of me, and that I was happy he had goals and a life outside of us. When we got back home he said he didn’t realize those things and he asked me if I would take him back. Obviously I did.

Three months passed without those break-up conversations. Then one day he started to get quiet and seemed uninterested in a lot of things, even me. I took it as he was stressed about his pocket book and had no outlet since he wasn’t smoking anymore.

So, for the fourth time we had the breakup talk.

I said he was an idiot and ridiculous for wanting to give up something that has been so good, taking it out on us when he gets overwhelmed with life and can’t cope with unforeseen responsibilities. As I was getting my things he told me he didn’t want me to go and asked me why I was fighting so hard for him and why things were so black and white with me. I could only tell him I had a lot to lose. That over the last few months  I let my feeling grow more and more  based off his actions. I thought his feelings had grown too. I brought up the fact that he had a lot of stressful things happen all at once in the last few weeks and asked if that was what really was bothering him and not our relationship. He thought about it for a while and then decided that I had a valid point and he didn’t want to break up.

Hopefully you can see why I’m beyond confused. I now find myself having trust issues after this last conversation and difficulty rebounding like I did before. There is open communication now, he’s telling me more about what is annoying him or things he wants to do alone. I can’t figure out what this man is thinking. If this is really what he wants or not. I’m worried he’s just trying to make me happy and not being true to himself and that’s the last thing I want even if I get hurt. Is he trying to fake it until he makes it? Should I just tuck tail and run?


Hi J,

What concerns us is simple. Every time his life gets stressful, he tends to want to push away everything that’s solid and steady in his life. (As you surmised.) And he seems to do that with relative ease. In fact, you’d be broken up already if you didn’t fight for the relationship to continue. From what you describe, he has yet to fight for the relationship himself, and that’s certainly a concern, and seems to be a pattern in his life, in his last relationship, and now yours.

So we can see why you’re having trust issues. Why wouldn’t you? He’s given you no reason to believe that he’s changed, or that he’s trying to change his behavior and his patterns.

Here’s a guy’s vicious cycle: 1. He’s not sure what he wants. 2. He pushes girlfriend away. Breaks up. 3. He says he doesn’t deserve her. 4. This makes her feel sad and guilty. She tries to comfort and reassure him. He’s still not sure. 5. But then he gets lonely. Horny. 6. She wants to try again. 7. He questions his initial breakup decision. Decides to try again too. Why not? Maybe he was a fool for leaving and things will be different. 8. Things are great for a time. Blissful even. 9. He starts to doubt himself. Realizes that maybe he should have stayed broken up. 10. Pattern repeats. (Often, the guy knows exactly what he wants or doesn’t want, but is afraid of hurting his partner.)

In general, once breakups begin, the relationship will eventually come to a conclusion. Yes, there are exceptions, but typically, the first breakup leads to the next, and the next, until the final breakup, or until the woman gets fed up and leaves.

Is your situation the exception or the rule? We can’t answer that. It’s hard to say. We tend to play the percentages. But it’s easy for us to say, and much harder for you to know.

Our advice: It’s time for a serious conversation about the future of the relationship. Stop making him think you’re okay being in a relationship with no expectations when clearly you’re not, at least not anymore. We’re not saying you’re pushing marriage, but it’s okay to say to the world, “I want this man; I want this relationship.” And it’s certainly okay to say it to him. Some women worry if it’s too soon to have this type of conversation, and early on, it might be. But you’re well past this point. Talk to him. Tell him what you want and that you can’t deal with his waffling. If he can’t give you a straight answer then you’ve got some serious thinking to do.

The Guy Conundrum: If he hasn’t figured out what he wants, then he’s figured out what he wants.

Final Thought: Sometimes, whether a relationship works or not, it just comes down to simply, timing. It’s frustrating to think, but in your case, it’s possible. We know this doesn’t help, because in some ways it gives false hope. But understand that bad timing is really the same as not connecting, even if that doesn’t make a lot of sense.

Questions? Thoughts?

Take care,


ps. Please let your friends know about us. Thanks!

Also Read More: Relationship Advice and Dating Advice on Breaking Up

Breaking up

What do I do now? How can I leave my relationship?

Getting back together: Is it possible?

Was breaking up with him the right thing to do? 

Will he come back? 







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