Think it depends on the chick. For some, it could be an Alpha male thing that shows you can make it through tough shit and still have a level head. For others it could be a deal breaker. I wouldn't boast about it, but even if she doesn't like that fact, it is something that can be easily overcome (Unless she walks away just from that. And in that case, forget her for being closed minded. On to the next)
i c what u mean, but if i did say that to someone, how would i say it too them without seeming like im bragging?
i only bring up the times ive been arrested when im talking about silly sh*T from my past. or the girl brings up something illegal shes done. like said above becareful, it can be a deal breaker. some girls dont find bad boys "good".
As stated before it depends on the girl, but also how you bring it up. the girl who likes the bad boy will like a bit of the bragging, but dont say it like you are proud of it. Just say something, when the times comes up, "yeah I was in jail for a while. That stuff they show on tv and movies is not totally exaggerated. Some shit goes down in there. Luckily I never shanked or raped! But the politics, fights, and horrible conditions are all true"
If its a girl who doesnt like that type of thing you have to go about it differently, if you ever even want to bring it up (there are some things , In my opinion you should take to the grave). It would have to be during a deeeeep conversation where she is also admitting to some skeletons in her closet....then bring it up nonchalantly "Everyone makes mistakes they are not proud of. For instance Its amazing how many different types of people are in jail for pretty bad stuff and also ridiculous stuff. I was in jail for a while and met this guy who did ( say something awful that someone was in there for) anbd this other guy who was doing XXX amount of time for (say something stupid that seems incredible they are in there...i knew a guy when I was in that got locked up for hitting a pizza box, the box hit the girl on the thigh, and he got charged with domestic violence)." She will of course ask why you were in there, and as long as its not murder, rape, or shit involving kids.....you are ok to tell what you were in there for and how it happened. Most girls will be on your side once they hear your side of the story and you prep them with the "This monster i knew did this" and "this poor sap didnt do shit but got lucked up. the system can be fucked".