How do I know I should jump in the relationship?

[Anonymous]

Been conflicted on completely trusting this guy.

We’ve known each other for about more than an year but started to seriously talk for 3 months on a regular basis. He’s a guy who respects my time boundaries, fun to talk to, incredibly kind, and been pretty consistent. I think I like him and I think he might like me back. However, he had a rough history. He has a background of his dad often cheating, extended family cheating, and his past exes cheating on him. His extended family and his family also constantly compare each other’s achievements. On the contrary, my parent’s marriage has been faithful and I’ve never been in a relationship before (been scared of getting into one). My close friends say that I shouldn't trust/like him. But, there isn’t a direct reason of what he’s done as to why I shouldn’t. He claims he doesn’t seem like to be the type to cheat nor have cheated in the past and from talking to him it feels like he’s telling the truth. He’s also shared that he wants to live a more peaceful life and get away from the lifestyle he’s currently dealing with.

TDLR: As a person I think our values and chemistry match pretty well. But, his history and background worries me that it’ll cause problems in the future. Is it really worth on possibly getting hurt in the end then?

[DaveJord]

I would say that after a year or more of talking and after 3 months of constant talking, that you already know how you feel about this situation and what you should be doing about it without me giving and opinion.

So let me say this, as a man, after I meet a woman and talk to her for a week or two at the most, I am asking her out. If I am seriously interested, I would keep the conversation going for about a month, tops... but if we have not meet or are not dating or seriously progressing the relationship in any way after a month, I am done with her. That is because I am not a guy looking for quick score. I am looking for something and if it's that difficult for you to decide then I am obviously not the guy for you, and you definitely are not the women for me. If after a few dates, or weeks of texting and conversations you still are that undecided then it's not going to work for me and that is pretty much it. But like I said I am not looking for a quick score.

Now there are other types of guys that let these things drag on and on, and on... because eventually they get what they want from it and then move on. But up until that point they play a long and say all the right things, and do the right things, to really give the women the maximum amount of time and space... then they get what they want and realize it's not worth hanging around for the long term. This is fine to them because they got what they wanted.

So successful, accomplished and good intentioned guys, do not really hang out long enough for you to string these types of things out as long as this thing has been strung out. Over a year or so... you're interested but not really too interest, but showing enough interest to keep him coming back or hang round... but not really sure if you are ready yet to act on it. You're still not really sure if he's done enough to prove to you, he's really worth it. This is called playing hard to get, and most women don't do it on purpose or are even aware of the that they are doing it. But by this point most good men would be worn out and done with it. So, the fact that his guy is not is concerning to me... and the fact that you really haven't figure this out for yourself by now after a year of stringing this guy a long is an even bigger RED FLAG to me.

I would say trust your instincts.

[Guy13]

If the men in his line that cheat are Narcissist then there is be a malformation. Their brain is different. You need 6 months regularity around family and see if dad or like smacks your butt and tries to dominate you and/or him. That can be genetic. You guys should share medical, criminal, credit, and current STD info before going all in.

[slatyb]

Don't judge him by his family. Many lovely people come from troubled families. Judge him by his behavior.