I have been seeing a man for about 9 months, and there have been disagreements and 2 break ups but all seemed trivial. I thought we would become closer as time went on as we are both older and been alone for many years so stuck in our ways. The last break I said I wouldn't make any more contact and would leave him alone forever as I found the breakups so difficult and always contacted him everyday even though we were meant to have split. Of course, this time after 2 weeks, I'm finding myself really wanting to email him saying how much I miss him. The thing is the negatives become fainter and the good times more in the front of my mind and there's regret that there's so much of him I never got to know and so many things for us to do together.He seemed to have a difficult personality which I found hard to work out, for example a few times he would say he's not leaving his house but I was welcome to go there, even if it was his turn to come to my house. A bit uncompromising which made me very frustrated. This is my first experience back on the dating scene for ages and think I might need to toughen up but on the other hand I think about what we could have together if I contacted him.

I think that if you are coming back to dating after ages of being away from it it is important to redefine what it is you want.
The fact that you broke up twice tells me that the problems that came up the first time were not properly addressed. I think you both need some time to just let the dust settle for a while so , that both of you can look at the relationship objectively. Find out what the issues are and if you can or want to fix them. That also depends on whether he wants to work with you as well.

But, 2 breakups are a pretty good red flag. The last thing you want to do it get caught up in a breakup/get back together wheel.
It may be in your better interest to go out and date other people, explore what is out there... that way you have some comparisons and can understand better who you want to be with.

Thanks your reply, it is really helpful. Looking at it sensibly taking a step back and meeting new people would be the right way to go. Sometimes you just need other people to tell you so.

Talaniman Rule - Don't miss other opportunities and options because your stuck on someone who is not as stuck on you, that’s just plain crazy.

Iin nine months, disagreements are normal, but, 2 breakups, and you characterize them as being 'trivial'. Can you elaborate on the reason for the breakups?

And when you did return, how were things resolved. Did the two of you have some good conversation going on, and did you both listen and talk to each other with respect? Anything resolved or negotiated after the air was cleared?

In the meanwhile, do you think you miss him, more than you miss the company? Have you a social life independent of him; friends, family, interests? Is it better to try to make the relationship work, or move on and find another partner that is perhaps more compatible.

If he's worth fighting for, and you are prepared to make the investment of time and commitment, you might want to consider alternative ways to better communcate your needs and wants. If he too, is willing to make a commitment, why not try couples counselling to address the roadblocks the two of you hit, that have thus far resulted in two splits. Maybe if the two of you learned to communicate more effectively, you can work past your differences enough to find that maybe there is more to staying together, than giving up.