Long term relationships- when do you let go?

Everyone "knows" a long history together shouldn't keep two people together when they aren't really happy anymore...

But how do you know when its time to move on?

My bf and I (of 3 solid-5 dating yrs) recently broke up over the summer due to his stress of graduating college and not being able to find a job, and me getting upset over a situation with a girl friend of his. We had planned to move together when he got a job, and so it kind of stung when he just dumped me after arranging my school schedule to suit a move and everything.

We decided to try to work things out after a 2 month breakup, but since he made out with one friend and then slept with her bestfriend only 2 weeks after we split its made me question things. (I also made uot with a friend, but did not have sex!) He told me right after and apologized deeply and said he realized how much I meant to him after that, but I dunno...

He's always been wishy-washy about his feelings, and I'm kinda of getting tired of waiting for him to grow up and be the partner I need in our relationship. However, we both have issues to work on, naturally. I do love him very, very much, but after the breakup I guess I realized I'd be miserable for a long time, but I won't DIE without him and so I need to make a logical decision before he gets a job and he moves (or he and I move) away.

I'm almost 24 and he's 25. I live with my Grandfather since my Gma passed 3 yrs ago, and it helps with tuition costs though I work full time. He's still living at home waiting to get hired on, but with the economy its tough. So obviously we're both under stress as well.

I'm just trying to decide if someone making an effort to be "nice" and do nice things for you (when they're unhappy with themselves) is enough to warrant continuing this relationship. I feel like something's broken and I'm not really sure how to fix it....

Well, I think that any 'activity' that took place while you two were broken up really doesn't hold much ground to pit against him (you weren't dating anymore, right?)

I think the question as to whether or not you want to reconcile your relationship with him rests on what *you* want out of a relationship at this current stage of your life.
Do you want a boyfriend or a husband? Are you financially secure enough to sustain such a relationship? Maybe take a pen out and write down all the things you want at the current time, then make an informed decision based on those ideals.

~Wandering Author

Yeah, I know that its not technically wrong, but it still makes you wonder how he could have so easily bedded another girl. And it wasn't a drunken accident either...

We've had issues in the past (not to get into a lengthy essay) with his character when it comes to judgement calls.

He's slept with 2 close sisters, not telling the one who really liked him and slept with her anyway as well. Still friends with her to this day and she doesnt know.

He slept with the 1st friend's best friend after making out with her, and didn't tell the 1st friend who likes him...

He's had various sexual encounters that just don't sit well with me and the fact that he hides them from people is what makes me most nervous. I wonder if he's capable of deceiving his friends this way, what does that say about him?

I guess the reason it bothers me is not the sex so much, but the lying to the friends and the inappropriate behavior which crosses the friend rules. I thought he had grown out of that... and it worries me that he recently did something so similar I suppose.

Does that make any sense?

But yes, you have a very good point. I need to decide what I want, and whether he can give it to me or not. Its just hard when you aren't sure if that person is really incompatible, or just stuck in a 20-something year old growing up stage, you know?